cas 119-36-8, Methyl salicylate | Articles data

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Novel aroylhydrazine-amide derivatives bearing pyridine core: Synthesis, characterisations and selective colorimetric recognition properties
Four aroylhydrazine-amides receptors AR1-4 with a hydrazine spacer have been designed, synthesised and characterised as novel colorimetric chemosensors by typical spectroscopic techniques. The receptors AR1-3 exhibited certainly selectivity and sensitivity towards F- and AcO-, forming 1:1 stoichiometry complex by hydrogen-bond interaction. Furthermore, AR4 has especially shown obvious colour change in the presence of these two important biologically anions.
Li, Shaowei,Li, Huangyong,Chen, Changshui,Yue, Xiali,Cao, Xiufang,Ke, Shaoyong
p. 384 - 392
(2013)
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New highly selective turn-on fluorescence receptor for the detection of copper (II)
Three new receptors (1a–c) bearing a p-dimethylaminobenzamide fluorophore have been synthesized and evaluated in terms of their fluoroionophoric properties towards various metal ions. Notably, receptors 1a and 1c exhibited dramatic fluorescent enhancement towards Cu2?+ in acetonitrile. Subsequent investigations revealed that the highly selective behavior of these receptors towards Cu2?+ could be attributed to the Cu2?+-mediated oxidative cyclization of these compounds to the corresponding 1,3,4-oxadiazoles. Solvent effects and quantum calculations indicated that 1a and 1c both possessed an intramolecular charge transfer channel, which could be obstructed by the oxidative cyclization of these receptors. Receptor 1a was successfully applied to the determination of the Cu2?+ in drug sample with a low detection limit of 2.2?×?10??8?mol?L??1.
Nan, Qian,Rong, Pu,Jiang, Yunbao,Yang, Rui
p. 307 - 315
(2017)
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Clinton,Laskowski
p. 3135
(1948)
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Exploring naphthyl-carbohydrazides as inhibitors of influenza A viruses
A library of hydrazide derivatives was synthesized to target non-structural protein 1 of influenza A virus (NS1) as a means to develop anti-influenza drug leads. The lead compound 3-hydroxy-N-[(Z)-1-(5,6,7,8-tetrahydronaphthalen-2-yl) ethylideneamino]naphthalene-2-carboxamide, which we denoted as "HENC", was identified by its ability to increase the melting temperature of the effector domain (ED) of the NS1 protein, as assayed using differential scanning fluorimetry. A library of HENC analogs was tested for inhibitory effect against influenza A virus replication in MDCK cells. A systematic diversification of HENC revealed the identity of the R group attached to the imine carbon atom significantly influenced the antiviral activity. A phenyl or cyclohexyl at this position yielded the most potent antiviral activity. The phenyl containing compound had antiviral activity similar to that of the active form of oseltamivir (Tamiflu), and had no detectable effect on cell viability.
Barman, Sanmitra,You, Lei,Chen, Ran,Codrea, Vlad,Kago, Grace,Edupuganti, Ramakrishna,Robertus, Jon,Krug, Robert M.,Anslyn, Eric V.
p. 81 - 90
(2014)
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Novel amide-type ligand bearing bis-pyridine cores: Synthesis, spectral characterizations and X-ray structure analyses
The novel salicylamide-type ligand containing bis-pyridine moieties, i.e. 2-((6-chloropyridin-3-yl)methoxy)-N-(2-((6-chloropyridin-3-yl)methylthio)phenyl)benzamide, which has been successfully synthesized and characterized by typical spectroscopic techniques mainly including IR, 1H NMR and ESI-MS. The structure of target compound was further determined by single crystal X-ray diffraction method and which crystallized in the monoclinic system with space group P2(1)/c.
Ke, Shaoyong
p. 91 - 97
(2016)
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Sowa,Nieuwland
p. 271
(1936)
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A catalyst-free, facile and efficient approach to cyclic esters: Synthesis of 4H-benzo[d][1,3]dioxin-4-ones
We have developed a green and practical method to construct 4H-benzo[d][1,3]dioxin-4-one and its derivatives, which are important structural units in insecticides, and intermediates to synthesize multiple-substituted benzene derivatives of great value. The catalyst- and additive-free conditions, commercial and cheap starting materials and short reaction time, make this transformation practical and attractive.
Lin, Feng,Song, Qiuling,Gao, Yuyu,Cui, Xiuling
p. 19856 - 19860
(2014)
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Synthesis of 2H-1,3-benzoxazin-4(3H)-one derivatives containing indole moiety: Their in vitro evaluation against PDE4B
A number of 2H-1,3-benzoxazin-4(3H)-one derivatives containing indole or benzofuran moieties were synthesized by using Pd/C-Cu mediated coupling-cyclization strategy as a key step. The o-iodoanilides or o-iodophenol were coupled with 3-{2-(prop-2-ynyloxy)ethyl}-2H-benzo[e][1,3]oxazin-4(3H)-one using 10%Pd/C-CuI-PPh3 as a catalyst system and Et3N as a base to give the target compounds. All the synthesized compounds were tested for their PDE4B inhibitory potential in vitro using a cell based cAMP reporter assay. Some of them showed fold increase of the cAMP level when tested at 30 μM. A representative compound showed encouraging PDE4B inhibitory properties that were supported by its docking results.
Rao, Raja Mohan,Luther, Bethala Jawahar,Rani, Chekuri Sharmila,Suresh, Namburi,Kapavarapu, Ravikumar,Parsa, Kishore V.L.,Rao, Mandava V. Basaveswara,Pal, Manojit
p. 1166 - 1171
(2014)
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Photocatalytic C–H activation and oxidative esterification using Pd@g-C3N4
Graphitic carbon nitride supported palladium nanoparticles, Pd@g-C3N4, have been synthesized and utilized for the direct oxidative esterification of alcohols using atmospheric oxygen as a co-oxidant via photocatalytic C–H activation.
Verma, Sanny,Nasir Baig,Nadagouda, Mallikarjuna N.,Varma, Rajender S.
p. 248 - 252
(2018)
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Anticancer activity ofwater-soluble olsalazine-pamam-dendrimer-salicylic acid-conjugates
Improving the activity and selectivity profile of anticancer agents will require designing drug carrier systems that employ soluble macromolecules. Olsalazine-PAMAM-dendrimer-salicylic acid-conjugates with dendritic arms of different lengths have shown good stability regarding the chemical link between drug and spacer. In this study, the drug release was followed in vitro by ultraviolet (UV) studies. Evaluation of the cytotoxicity of the olsalazine-PAMAM-dendrimer-salicylic acid-conjugates employing a sulforhodamine B (SRB) assay in PC-3 (human prostatic adenocarcinoma) and MCF-7 (human mammary adenocarcinoma) cell lines demonstrated that conjugate 9 was more active as an antiproliferative agent than cisplatin, and no cytotoxicity towards the African green monkey kidney fibroblast (COS-7) cell line was observed in any of the conjugates synthesized in the present work.
Cortez-Maya, Sandra,Pedro-Hernández, Luis Daniel,Martínez-Klimova, Elena,Ramírez-ápan, Teresa,Martínez-García, Marcos
(2019)
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ON THE BIOSYNTHESIS OF BENZOIC ACID IN GAULTHERIA PROCUMBENS L. II.
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GRISEBACH,VOLLMER
(1964)
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Klosa
p. 125
(1956)
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Discovery of new VEGFR-2 inhibitors based on bis([1, 2, 4]triazolo)[4,3-a:3',4'-c]quinoxaline derivatives as anticancer agents and apoptosis inducers
Herein, a new wave of bis([1, 2, 4]triazolo)[4,3-a:3',4'-c]quinoxaline derivatives have been successfully designed and synthesised. The synthesised derivatives were biologically investigated for their cytotoxic activities against HepG2 and MCF-7. Also, the tested compounds were further examined in?vitro for their VEGFR-2 inhibitory activity. The most promising derivative 23j was further investigated for its apoptotic behaviour in HepG2 cell lines using flow cytometric and western-plot analyses. Additional in-silico studies were performed to predict how the synthesised compounds can bind to VEGFR-2 and to determine the drug-likeness profiling of these derivatives. The results revealed that compounds 23a, 23i, 23j, 23l, and 23n displayed the highest antiproliferative activities against the two cell lines with IC50 values ranging from 6.4 to 19.4 μM. Furthermore, compounds 23a, 23d, 23h, 23i, 23j, 23l, 23 m, and 23n showed the highest VEGFR-2 inhibitory activities with IC50 values ranging from 3.7 to 11.8 nM, comparing to sorafenib (IC50 = 3.12 nM). Moreover, compound 23j arrested the HepG2 cell growth at the G2/M phase and induced apoptosis by 40.12% compared to the control cells (7.07%). As well, such compound showed a significant increase in the level of caspase-3 (1.36-fold), caspase-9 (2.80-fold), and BAX (1.65-fold), and exhibited a significant decrease in Bcl-2 level (2.63-fold).
Alsaif, Nawaf A.,Taghour, Mohammed S.,Alanazi, Mohammed M.,Obaidullah, Ahmad J.,Al-Mehizia, Abdulrahman A.,Alanazi, Manal M.,Aldawas, Saleh,Elwan, Alaa,Elkady, Hazem
p. 1093 - 1114
(2021)
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Heinzelmann,W.,Maerky,M.
p. 376 - 382
(1974)
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Dealkylation of alklyl and aryl ethers with AlCl3-NaI in the absence of solvent
A facile synthetic procedure, for dealkylation of alkyl and aryl ethers with AlCl3-NaI in the absence of solvent is developed. We have been able to deprotect different methyl ethers in excellent yields.
Ghiaci, Mehran,Asghari, Jila
p. 973 - 979
(1999)
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Mack,Pinhey
p. 451
(1972)
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Design, synthesis, and molecular docking of novel 3,5-disubstituted-1,3,4-oxadiazole derivatives as iNOS inhibitors
To obtain new anti-inflammatory agents, recent studies have aimed to replace the carboxylate functionality of nonsteroidal anti-inflammatory drugs with less acidic heterocyclic bioisosteres like 1,3,4-oxadiazole to protect the gastric mucosa from free carboxylate moieties. In view of these observations, we designed and synthesized a series of 3,5-disubstituted-1,3,4-oxadiazole derivatives as inhibitors of prostaglandin E2 (PGE2) and NO production with an improved activity profile. As initial screening, and to examine the anti-inflammatory activities of the compounds, the inhibitions of the productions of lipopolysaccharide-induced NO and PGE2 in RAW 264.7 macrophages were evaluated. The biological assays showed that, compared with indomethacin, compounds 5a, 5g, and 5h significantly inhibited NO production with 12.61 ± 1.16, 12.61 ± 1.16, and 18.95 ± 3.57 μM, respectively. Consequently, the three compounds were evaluated for their in vivo anti-inflammatory activities. Compounds 5a, 5g, and 5h showed a potent anti-inflammatory activity profile almost equivalent to indomethacin at the same dose in the carrageenan-induced paw edema test. Moreover, the treatment with 40 mg/kg of 5h produced significant anti-inflammatory activity data. Furthermore, docking studies were performed to reveal possible interactions with the inducible nitric oxide synthase enzyme. Docking results were able to rationalize the biological activity data of the studied inhibitors. In summary, our data suggest that compound 5h is identified as a promising candidate for further anti-inflammatory drug development with an extended safety profile.
Koksal, Meric,Dedeoglu-Erdogan, Ayca,Bader, Marwa,Gurdal, Enise E.,Sippl, Wolfgang,Reis, Rengin,Ozgurbuz, Melda,Sipahi, Hande,Celik, Turgay
(2021)
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Hirao,Yonemitsu
p. 812
(1972)
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Chromatography-free, Mitsunobu-triggered heterocyclizations of salicylhydroxamic acids to 3-hydroxybenzisoxazoles
The Mitsunobu reaction has become one of the most powerful tools to alkylate acidic pronucleophiles. A significant caveat of Mitsunobu chemistry, however, is that the reaction mixture is often plagued with purification problems owing to the phosphine oxide and hydrazine dicarboxylate by-products. In addition to the development of more readily separable Mitsunobu reagents, the product's physicochemical properties may be exploited to facilitate purification. In this regard, we present a swift and efficient preparation of 3-hydroxybenzisoxazoles by the Mitsunobu-triggered heterocyclizations of salicylhydroxamic acids, which can be isolated by an acid–base work-up. As expected, a range of functional groups was compatible with the chemistry.
Van Eker, Daniel,Chauhan, Jay,Murphy, William A.,Conlon, Ivie L.,Fletcher, Steven
p. 5301 - 5303
(2016)
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A Copper(II) tris-imidazolylphosphine complex as a functional model of flavonol 2,4-dioxygenase
Reaction of tetrakis(acetonitrile)copper(I) perchlorate ([Cu(NCCH3)4][ClO4]), tris-1-ethyl-4-methylimidazolylphosphine (T1Et4MeIP) (1) and 3-hydroxyflavone (flavH) under ambient conditions produces an in-situ generated flavonol bound copper(II) complex, which converts to a stable green complex that formulates to [Cu(T1Et4MeIP)(flav)][ClO4] (2). The crystal structure of 2 was determined by X-ray diffraction and crystallizes in a triclinic system (P1ˉ) with unit cell dimensions of a = 14.537(15) ?, b = 15.794(14) ?, c = 17.044(17) ?, α = 65.58(3)?, β = 86.80(5)?, γ = 73.34(4)?, V = 3376(6) ?3 and Z = 2. While the five-coordinate copper(II) complex is stable under ambient conditions in the solid state, it undergoes oxidative scission of the flavonol pyrone ring under photolytic (300 nm) and/or thermal (120 °C) conditions in the presence of molecular oxygen. The degradative process produces the corresponding methylated products: methylbenzoate, methyl salicylate and N,N-dimethylbenzamide. In addition, the previously undisclosed single crystal X-ray structure of tris-1-ethyl-4-methylimidazolylphosphine (1), T1Et4MeIP, is also reported.
Lynch, Will E.,Nivens, Delana,Quillian, Brandon,Padgett, Clifford W.,Petrillo, Anthony,Peek, Nathan,Stone, John
p. 99 - 106
(2019)
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POLYCYCLIC AMIDES AS UBE2K MODULATORS FOR TREATING CANCER
Provided are compounds of Formula (I) and pharmaceutically acceptable salts and compositions thereof, which are useful for treating conditions associated with modulation of UBE2K.
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Paragraph 00173-00175

(2021/07/10)

New quinoxaline-based VEGFR-2 inhibitors: Design, synthesis, and antiproliferative evaluation with: In silico docking, ADMET, toxicity, and DFT studies
A new series of 3-methylquinoxaline-based derivatives having the same essential pharmacophoric features as VEGFR-2 inhibitors have been synthesized and evaluated for their antiproliferative activities against two human cancer cell lines, MCF-7 and HepG-2. Compounds 15b and 17b demonstrated a significant antiproliferative effect with IC50 ranging from 2.3 to 5.8 μM. An enzymatic assay was carried out for all the tested candidates against VEGFR-2. Compound 17b was the most potent VEGFR-2 inhibitor (IC50 = 2.7 nM). Mechanistic investigation including cell cycle arrest and apoptosis was performed for compound 17b against HepG-2 cells, and the results revealed that 17b induced cell apoptosis and arrested cell cycle in the G2/M phase. Moreover, apoptosis analyses were conducted for compound 17b to evaluate its apoptotic potential. The results showed upregulation in caspase-3 and caspase-9 levels, and improving the Bax/Bcl-2 ratio by more than 10-fold. Docking studies were performed to determine the possible interaction with the VEGFR-2 active site. Further docking studies were carried out for compound 17b against cytochrome P450 to present such compounds as non-inhibitors. In silico ADMET, toxicity, and physico-chemical properties revealed that most of the synthesized members have acceptable values of drug-likeness. Finally, DFT studies were carried out to calculate the thermodynamic, molecular orbital and electrostatic potential properties.
Alanazi, Manal M.,Alanazi, Mohammed M.,Alharbi, Madhawi A.,Alkahtani, Hamad M.,Alsaif, Nawaf A.,Dahab, Mohammed A.,Eissa, Ibrahim H.,Elkady, Hazem,Obaidullah, Ahmad J.
p. 30315 - 30328
(2021/10/25)

Design, modification of phyllanthone derivatives as anti-diabetic and cytotoxic agents
Twelve benzylidene derivatives, one Baeyer-Villiger oxidative, six imine derivatives were successfully designed and synthesised from phyllanthone. In the search for potential new anti-diabetic agents, phyllanthone along with its benzylidene and oxidation analogues were evaluated for enzyme inhibition against α-glucosidase. In the benzylidene series, most analogues displayed stronger activity than the mother compound. Compound 1c revealed the strongest activity, outperforming the acarbose positive control with an IC50 value of 19.59 μM. Phyllanthone and its derivatives were then tested for cytotoxic activity against the K562 cell line. The imine analogues displayed the most powerful cytotoxic activity with 3cand 3d having IC50 values of 57.55 and 68.02 μM, respectively.
Nguyen, Ngoc-Hong,Vo, Van-Giau,Phan, Hoang-Vinh-Truong,Ngo, Thanh-The,Sichaem, Jirapast,Nguyen, Thi-Phuong,Nguyen, Huu-Hung,Pham, Duc-Dung,Nguyen, Tien-Cong,Nguyen, Van-Kieu,Duong, Thuc-Huy
supporting information
p. 371 - 378
(2020/07/13)

Development of phenyltriazole thiol-based derivatives as highly potent inhibitors of DCN1-UBC12 interaction
Defective in cullin neddylation 1(DCN1) is a co-E3 ligase that is important for cullin neddylation. Dysregulation of DCN1 highly correlates with the development of various cancers. Herein, from the initial high-throughput screening, a novel hit compound 5a containing a phenyltriazole thiol core (IC50 value of 0.95 μM for DCN1-UBC12 interaction) was discovered. Further structure-based optimization leads to the development of SK-464 (IC50 value of 26 nM). We found that SK-464 not only directly bound to DCN1 in vitro, but also engaged cellular DCN1, suppressed the neddylation of cullin3, and hindered the migration and invasion of two DCN1-overexpressed squamous carcinoma cell lines (KYSE70 and H2170). These findings indicate that SK-464 may be a novel lead compound targeting DCN1-UBC12 interaction.
Zhou, Wenjuan,Xu, Chenhao,Dong, Guanjun,Qiao, Hui,Yang, Jing,Liu, Hongmin,Ding, Lina,Sun, Kai,Zhao, Wen
(2021/03/24)

DUAL ANDROGEN RECEPTOR/AKR1C3 INHIBITORS
The present invention provides benzamide compounds, compositions containing the benzamides, and use of the benzamides for inhibiting androgen receptor (AR) and/or aldo-keto reductase family 1 member C3 (AKR1C3). Also described herein methods for the treatment of hormone-mediated diseases and conditions, including hormone-related cancers such as castration resistant prostate cancer.
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Paragraph 0139-0140

(2021/05/29)

N-acylhydrazones confer inhibitory efficacy against New Delhi metallo-β-lactamase-1
The expression of β-lactamases, especially metallo-β-lactamases (MβLs) in bacteria is one of the main causes of drug resistance. In this work, an effective N-acylhydrazone scaffold as MβL inhibitor was constructed and characterized. The biological activity assays indicated that the synthesized N-acylhydrazones 1–11 preferentially inhibited MβL NDM-1, and 1 was found to be the most effective inhibitor with an IC50 of 1.2 μM. Analysis of IC50 data revealed a structure–activity relationship, which is that the pyridine and hydroxylbenzene substituents at 2-position improved inhibition of the compounds on NDM-1. ITC and enzyme kinetics assays suggested that it reversibly and competitively inhibited NDM-1 (Ki = 0.29 ± 0.05 μM). The synthesized N-acylhydrazones showed synergistic antibacterial activities with meropenem, reduced 4–16-fold MIC of meropenem on NDM-1- producing E. coli BL21 (DE3), while 1 restored 4-fold activity of meropenem on K. pneumonia expressing NDM-1 (NDM-K. pneumoniae). The mice experiments suggested that 1 combined meropenem to fight against NDM-K. pneumoniae infection in the spleen and liver. Cytotoxicity assays showed that 1 and 2 have low cytotoxicity. This study offered a new framework for the development of NDM-1 inhibitors.
Gao, Han,Li, Jia-Qi,Kang, Peng-Wei,Chigan, Jia-Zhu,Wang, Huan,Liu, Lu,Xu, Yin-Sui,Zhai, Le,Yang, Ke-Wu
(2021/07/07)

Method for hydrolyzing diarylether compound to generate aryl phenol compound
The invention discloses a method for hydrolyzing a diarylether compound to generate an arylphenol compound. According to the method, visible light is utilized to excite a photosensitizer for catalysis. In a reaction solvent, the raw material in the formula (1) breaks a C (sp2)-O bond under the auxiliary action of acid, and hydrolysis is performed to obtain the bimolecular aryl phenol compounds in the formula (3) and the formula (4). The method can catalyze the reaction at room temperature, is green and environment-friendly, and is easy to operate; the universality is wide, the reaction yield is relatively high, and the tolerance of functional groups is strong; the synthesis method not only can realize small-scale hydrolysis conversion of various diarylether compounds, but also can realize hydrolysis of herbicidal ether, triclosan and a lignin template substrate, and even can realize large-scale hydrolysis of triclosan and the lignin template substrate to realize gram-level degradation. A new strategy is provided for recovering phenol derivatives through lignin hydrolysis, degrading pesticides and purifying wastewater containing a degerming agent or herbicide. The method has wide application prospect and use value.
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Paragraph 0119-0123

(2021/09/29)

Ceramic boron carbonitrides for unlocking organic halides with visible light
Photochemistry provides a sustainable pathway for organic transformations by inducing radical intermediates from substrates through electron transfer process. However, progress is limited by heterogeneous photocatalysts that are required to be efficient, stable, and inexpensive for long-term operation with easy recyclability and product separation. Here, we report that boron carbonitride (BCN) ceramics are such a system and can reduce organic halides, including (het)aryl and alkyl halides, with visible light irradiation. Cross-coupling of halides to afford new C-H, C-C, and C-S bonds can proceed at ambient reaction conditions. Hydrogen, (het)aryl, and sulfonyl groups were introduced into the arenes and heteroarenes at the designed positions by means of mesolytic C-X (carbon-halogen) bond cleavage in the absence of any metal-based catalysts or ligands. BCN can be used not only for half reactions, like reduction reactions with a sacrificial agent, but also redox reactions through oxidative and reductive interfacial electron transfer. The BCN photocatalyst shows tolerance to different substituents and conserved activity after five recycles. The apparent metal-free system opens new opportunities for a wide range of organic catalysts using light energy and sustainable materials, which are metal-free, inexpensive and stable. This journal is
Yuan, Tao,Zheng, Meifang,Antonietti, Markus,Wang, Xinchen
p. 6323 - 6332
(2021/05/19)

Synthetic method of methyl salicylate
The invention discloses a synthesis method of methyl salicylate. The method comprises the following steps: preparing sodium phenolate by using caustic soda flakes and phenol as raw materials, carryingout carboxylation reaction on the obtained sodium phenolate and carbon dioxide gas to obtain sodium salicylate, reacting the obtained sodium salicylate with chloromethane gas under the action of a phase transfer catalyst to obtain a crude methyl salicylate product containing a toluene solvent, neutralizing and washing the crude methyl salicylate product, recovering the toluene solvent at normal pressure, and carrying out vacuum distillation to obtain a finished methyl salicylate product. According to the method, a strong acid catalyst is not used, so that the wastewater amount is greatly reduced, and the corrosion to equipment and the pollution to the environment are reduced. According to the method, equipment is not seriously corroded, the wastewater amount is small, and the process is more environmentally friendly.
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Paragraph 0016; 0018-0020; 0022-0024; 0026-0027

(2021/02/10)

Aryl phenol compound as well as synthesis method and application thereof
The invention discloses a synthesis method of an aryl phenol compound shown as a formula (3). All systems are carried out in an air or nitrogen atmosphere, and visible light is utilized to excite a photosensitizer for catalyzation. In a reaction solvent, ArNR1R2 as shown in a formula (1) and water as shown in a formula (2) are used as reaction raw materials and react under the auxiliary action of acid to obtain the aryl phenol compound as shown in a formula (3). The ArNR1R2 in the formula (1) can be primary amine and tertiary amine, can also be steroid and amino acid derivatives, and can also be drugs or derivatives of propofol, paracetamol, ibuprofen, oxaprozin, indomethacin and the like. The synthesis method has the advantages of cheap and easily available raw materials, simple reaction operation, mild reaction conditions, high reaction yield and good compatibility of substrate functional groups. The fluid reaction not only can realize amplification of basic chemicals, but also can realize amplification of fine chemicals, such as synthesis of drugs propofol and paracetamol. The invention has wide application prospect and use value.
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Paragraph 0092-0095

(2021/05/12)

Di(hydroperoxy)adamantane adducts: Synthesis, characterization and application as oxidizers for the direct esterification of aldehydes
The di(hydroperoxy)adamantane adducts of water (1) and phosphine oxides p-Tol3PO·(HOO)2C(C9H14) (2), o-Tol3PO·(HOO)2C(C9H14) (3), and Cy3PO·(HOO)2C(C9H14) (4), as well as a CH2Cl2 adduct of a phosphole oxide dimer (8), have been created and investigated by multinuclear NMR spectroscopy, and by Raman and IR spectroscopy. The single crystal X-ray structures for 1-4 and 8 are reported. The IR and 31P NMR data are in accordance with strong hydrogen bonding of the di(hydroperoxy)adamantane adducts. The Raman ν(O-O) stretching bands of 1-4 prove that the peroxo groups are present in the solids. Selected di(hydroperoxy)alkane adducts, in combination with AlCl3 as catalyst, have been applied for the direct oxidative esterification of n-nonyl aldehyde, benzaldehyde, p-methylbenzaldehyde, p-bromobenzaldehyde, and o-hydroxybenzaldehyde to the corresponding methyl esters. The esterification takes place in an inert atmosphere, under anhydrous and oxygen-free conditions, within a time frame of 45 minutes to 5 hours at room temperature. Hereby, two oxygen atoms per adduct assembly are active with respect to the quantitative transformation of the aldehyde into the ester.
Arp, Fabian F.,Ashirov, Rahym,Bhuvanesh, Nattamai,Blümel, Janet
supporting information
p. 15296 - 15309
(2021/11/16)

Synthesis, structure and in vitro cytotoxicity testing of some 2-aroylbenzofuran-3-ols
Five 2-aroyl-5-bromobenzo[b]furan-3-ol compounds (two of which are new) and four new 2-aroyl-5-iodobenzo[b]furan-3-ol compounds were synthesized starting from salicylic acid. The compounds were characterized by mass spectrometry and 1H NMR and 13C NMR spectroscopy. Single-crystal X-ray diffraction studies of four compounds, namely, (5-bromo-3-hydroxybenzofuran-2-yl)(4-fluorophenyl)methanone, C15H8BrFO3, (5-bromo-3-hydroxybenzofuran-2-yl)(4-chlorophenyl)methanone, C15H8BrClO3, (5-bromo-3-hydroxybenzofuran-2-yl)(4-bromophenyl)methanone, C15H8Br2O3, and (4-bromophenyl)(3-hydroxy-5-iodobenzofuran-2-yl)methanone, C15H8BrIO3, were also carried out. The compounds were tested for their in vitro cytotoxicity on the four human cancer cell lines KB, Hep-G2, Lu-1 and MCF7. Six compounds show good inhibiting abilities on Hep-G2 cells, with IC50 values of 1.39-8.03?μM.
Anh, Dang Thi Tuyet,Cong, Nguyen Tien,Dat, Nguyen Dang,Dung, Pham Duc,Meervelt, Luc Van,Phuong, Tran Hoang,Trang, Huynh Thi Xuan,Trung, Vu Quoc,Tuyen, Nguyen Van
p. 874 - 882
(2020/09/23)

Fluorescent molecular probe for identifying and detecting oxalic acid as well as preparation method and application thereof
The invention discloses a fluorescent molecular probe for identifying and detecting oxalic acid as well as a preparation method and an application thereof, which relate to a probe for identifying anddetecting oxalic acid as well as the preparation method and the application thereof. The invention aims to solve the technical problems that the existing fluorescent probe for identifying and detecting oxalic acid by using a fluorescence method cannot realize quantitative detection, is poor in selectivity and is easily interfered by other organic acids. The structural formula of the fluorescent molecular probe of the present invention is in the specification. The preparation method of the fluorescent molecular probe comprises the following steps: 1, reacting salicylic acid, concentrated sulfuric acid and methanol to prepare an intermediate I; 2, preparing an intermediate II from the intermediate I and hydrazine hydrate; 3, carrying out a reaction on 8-hydroxyquinaldine, selenium dioxide and 1, 4-dioxane to prepare an intermediate III; 4, reacting the intermediate III with the intermediate II to obtain an intermediate IV; and 5, reacting the intermediate IV with Fe to obtain the probe. The oxalic acid is recognized and detected through fluorescence enhancement, the selectivity is high, interference of other organic acids is avoided, and the detection limit is 1.3*10 mol/L.The method can be used in environment and food fields.
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Paragraph 0038-0040; 0056-0058; 0074-0076

(2020/08/27)

Design, synthesis, and in vitro evaluation of novel 1,3,4-oxadiazolecarbamothioate derivatives of Rivastigmine as selective inhibitors of BuChE
Rivastigmine has been prescribed for the therapy of Alzheimer’s disease (AD) symptoms. This drug is classified in the carbamate derivative group that has dual activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). According to the structure of Rivastigmine and its performance, a new series of 5-aryl-1,3,4-oxadiazole-2-carbamothioate compounds I–XI was synthesized using structure-based drug discovery approaches. For this purpose a set of these compounds were designed with computational docking method and their interactions with amino acid residues in the active sites of AChE and BuChE checked out. The structures of synthesized compounds were established by physicochemical and spectroscopic methods. The carbamoyl moiety of Rivastigmine structure was modified to carbamothioate and the effects of 1,3,4-oxadiazole heterocycle as a pharmacophoric nucleus were investigated. The potential of the synthesized compounds I–XI was evaluated against two most known agents of AD (AChE and BuChE) to determine their IC50 values. The results of the docking showed the range of binding affinity for the best poses of ten individual conformers for any compounds (I–XI) was between ?7.81 (VI) and ?6.75 (II) kcal/mol. The results of biological experiments displayed that most synthetic compounds (I–VIII) showed moderate to excellent selective activity range against BuChE (0.51–69.44 μM). In vitro cytotoxicity evaluation of these compounds (I–XI) by MTT assay on human dermal fibroblast (HDF) cell line exhibited no activity against HDF. The compound VI [S-(5-(p-tolyl)-1,3,4-oxadiazol-2-yl) ethyl(methyl)carbamothioate] showed the most stable binding affinity (?7.81 kcal/mol) and the lowest IC50 value (0.51 μM) in comparison with Rivastigmine with 7.72 μM and Donepezil with 5.20 μM against BuChE.
Fallah, Akram,Mohanazadeh, Farajollah,Safavi, Maliheh
p. 341 - 355
(2019/12/30)

Synthesis and biological evaluation of novel 5,6,7-trimethoxy flavonoid salicylate derivatives as potential anti-tumor agents
5,6,7-Trimethoxy flavonoid salicylate derivatives were designed by the joining of three important pharmacophores (TMP, flavonoid, and SA) according to the combination principle. A series of novel trimethoxy flavonoid salicylate derivatives were synthesized and their in vitro anti-tumor activities were evaluated. Among these derivatives, compound 7f exhibited excellent antiproliferative activity against HGC-27 cells and MGC-803 cells with IC50 values of 10.26 ± 6.94 μM and 17.17 ± 3.03 μM, respectively. Subsequently, the effects on cell colony formation (clonogenic survival assay), cell migration (wound healing assay), cell cycle distribution (PI staining assay), cell apoptosis (Hoechst 33258 staining assay and annexin V-FITC/PI dual staining assay), lactate level (lactate measurement), microtubules disarrangement (immunofluorescence staining analysis) and docking posture (molecular docking simulation) were determined. Further western blot analysis confirmed that compound 7f could effectively down-regulate the expression of glycolysis-related proteins HIF-1α, PFKM and PKM2 and tumor angiogenesis-related proteins VEGF. Overall, these studies suggested that compound 7f, as the representative compound of those, might be a promising candidate for the treatment of gastric cancer and deserved the further studies.
Deng, Xiangping,Feng, Wanshi,Lei, Xiaoyong,Liu, Renbo,Peng, Yijiao,Tang, Guotao,Xie, Zhizhong,Xiong, Runde,Zheng, Xing,Zou, Yang
(2020/02/13)

Synthesis, anti-inflammatory activity, and molecular docking studies of some novel Mannich bases of the 1,3,4-oxadiazole-2(3H)-thione scaffold
A series of novel ibuprofen and salicylic acid-based 3,5-disubstituted-1,3,4-oxadiazole-2(3H)-thione derivatives was synthesized, and they were evaluated as potential anti-inflammatory agents. Following the structure identification studies employing IR, 1H nuclear magnetic resonance (NMR), 13C NMR, and elemental analysis, the title compounds were tested by cyclooxygenase (COX)-1 and COX-2 inhibition assays concomitant to lipopolysaccharide (LPS)-induced nitric oxide and prostaglandin production prevention experiments. The results indicated that the majority of the compounds displayed either a superior or comparable activity in preventing both LPS-induced NO production and COX-1 activity in comparison to the activities of the reference molecules. Furthermore, docking studies were also performed to reveal possible interactions with the COX enzymes.
Ozyazici, Tugce,Gurdal, Enise E.,Orak, Duygu,Sipahi, Hande,Ercetin, Tuba,Gulcan, Hayrettin O.,Koksal, Meric
(2020/04/28)

Preparation of Acifluorfen-Based Ionic Liquids with Fluorescent Properties for Enhancing Biological Activities and Reducing the Risk to the Aquatic Environment
In this work, 12 novel herbicidal ionic liquids (HILs) based on acifluorfen were prepared by pairing with the fluorescent hydrazides or different alkyl chains for increasing activities and reducing negative impacts on the aquatic environment. The results showed that the fluorescence of coumarin hydrazide in the HILs was applied as the internal and supplementary light source to meet the requirement of light wavelength range of acifluorfen, which improved the phytotoxicity of acifluorfen to weeds by enhancing singlet oxygen generation with increased sunlight utilization. The herbicidal activities of HILs were related positively with the length of chain of cation under high light intensity and depended mainly on the fluorescence characteristic of the cation under low light intensity, and the double salt IL forms of acifluorfen containing coumarin hydrazide and n-hexadecyltrimethylammonium had enhanced efficacies against broadleaf weeds in the field. Compared with acifluorfen sodium, HILs had lower water solubility, better surface activity, weaker mobility in soils, and higher decomposition temperature. These results demonstrated that HILs containing different cations provided a wider scope for fine-tuning of the physicochemical and biological properties of herbicides and established a promising way for the development of environmentally friendly herbicidal formulations.
Cao, Yongsong,Li, Jianqiang,Niu, Junfan,Tang, Gang,Tang, Jingyue,Tang, Rong,Yang, Jiale,Zhang, Wenbing,Zhou, Zhiyuan
p. 6048 - 6057
(2020/06/26)

Synthesis, α-glucosidase inhibition, and molecular docking studies of novel N-substituted hydrazide derivatives of atranorin as antidiabetic agents
A series of novel N-substituted hydrazide derivatives were synthesized by reacting atranorin, a compound with a natural depside structure (1), with a range of hydrazines. The natural product and 12 new analogues (2–13) were investigated for inhibition of α-glucosidase. The N-substituted hydrazide derivatives showed more potent inhibition than the original. The experimental results were confirmed by docking analysis. This study suggests that these compounds are promising molecules for diabetes therapy. Molecular dynamics simulations were carried out with compound 2 demonstrating the best docking model using Gromac during simulation up to 20 ns to explore the stability of the complex ligand-protein. Furthermore, the activity of all synthetic compounds 2–13 against a normal cell line HEK293, used for assessing their cytotoxicity, was evaluated.
Alam, Mahboob,Chavasiri, Warinthorn,Duong, Thuc-Huy,Huynh, Ngoc-Vinh,Nguyen, Huu-Hung,Nguyen, Thi-Phuong,Nguyen, Tien-Cong,Paramita Devi, Asshaima,Phan, Hoang-Vinh-Truong,Sichaem, Jirapast,Tran, Hoai-Duc,Tran, Nguyen-Minh-An
(2020/07/10)

Modulation of estrogen-related receptors subtype selectivity: Conversion of an ERRβ/γ selective agonist to ERRα/β/γ pan agonists
Estrogen Related Receptors (ERRs) are key regulators of energy homeostasis and play important role in the etiology of metabolic disorders, skeletal muscle related disorders, and neurodegenerative diseases. Among the three ERR isoforms, ERRα emerged as a potential drug target for metabolic and neurodegenerative diseases. Although ERRβ/γ selective agonist chemical tools have been identified, there are no chemical tools that effectively target ERRα agonism. We successfully engineered high affinity ERRα agonism into a chemical scaffold that displays selective ERRβ/γ agonist activity (GSK4716), providing novel ERRα/β/γ pan agonists that can be used as tools to probe the physiological roles of these nuclear receptors. We identified the structural requirements to enhance selectivity toward ERRα. Molecular modeling shows that our novel modulators have favorable binding modes in the LBP of ERRα and can induce conformational changes where Phe328 that originally occupies the pocket is dislocated to accommodate the ligands in a rather small cavity. The best agonists up-regulated the expression of target genes PGC-1α and PGC-1β, which are necessary to achieve maximal mitochondrial biogenesis. Moreover, they increased the mRNA levels of PDK4, which play an important role in energy homeostasis.
Avdagic, Amer,Billon, Cyrielle,Burris, Sheryl L.,Burris, Thomas P.,Elagawany, Mohamed,Elgendy, Bahaa,Goher, Shaimaa S.,Hegazy, Lamees,Sanders, Ryan,Shahien, Mohamed,Sitaula, Sadichha
(2020/07/21)

Ultralow-Molecular-Weight Stimuli-Responsive and Multifunctional Supramolecular Gels Based on Monomers and Trimers of Hydrazides
The simpler, the better. A series of simple, neutral and ultralow-molecular-weight (MW: 140–200) hydrazide-derived supramolecular gelators have been designed and synthesized in two straightforward steps. For non-conjugated cyclohexane-derived hydrazides, their monomers can self-assemble to form gels through intermolecular hydrogen bonds and dipole-dipole interactions. Significantly, conjugated phthalhydrazide can self-aggregate into planar and circular trimers through intermolecular hydrogen bonds and then self-assemble to form gels through intermolecular π–π stacking interactions. It is interesting that these simple gelators exhibit unusual properties, such as self-healing, multi-response fluorescence, and visual and selective recognition of chiral (R)/(S)-1,1′-binaphthalene-2,2′-diamine and S2? through much different times of gel re-formation and blue-green color change, respectively. These results underline the importance of supramolecular gels and extend the scope of supramolecular gelators.
Wu, Dehua,Song, Jintong,Qu, Lang,Zhou, Weilan,Wang, Lei,Zhou, Xiangge,Xiang, Haifeng
supporting information
p. 3370 - 3378
(2020/10/02)

Mechanistic Studies on the Salicylate-Catalyzed Peroxyoxalate Chemiluminescence in Aqueous Medium
The peroxyoxalate reaction is one of the most efficient chemiluminescence transformations known and the only system occurring by an intermolecular chemically initiated electron exchange luminescence (CIEEL) mechanism with confirmed high quantum yields. The peroxyoxalate chemiluminescence (PO-CL) is mainly studied in anhydrous organic medium; however, for bioanalytical application, it should be performed in aqueous media. In the present work, we study the peroxyoxalate system in a binary 1,2-dimethoxyethane/water mixture with bis(2,4,6-trichlorophenyl) oxalate (TCPO), bis(4-methylphenyl) oxalate (BMePO) and bis[2-(methoxycarbonyl)phenyl] oxalate (DMO), catalyzed by sodium salicylate, in the presence of rhodamine 6G as activator. Reproducible kinetic results are obtained for all systems; emission decay rate constants depend on the salicylate as well as hydrogen peroxide concentration, and the occurrence of a specific base catalysis is verified. Although singlet quantum yields determined are lower than in anhydrous media in comparable conditions, they are still considerably high and adequate for analytical applications. The highest singlet quantum yields are obtained for the “ecologically friendly” derivative DMO indicating that this derivative might be the most adequate substrate for the use of the peroxyoxalate system in bioanalytical applications.
Cabello, Maidileyvis C.,Souza, Glalci A.,Bello, Liena V.,Baader, Wilhelm J.
p. 28 - 36
(2020/01/08)

Method for preparing alcohol and phenol through aerobic hydroxylation reaction of boric acid derivative in absence of photocatalyst
The invention discloses a method for preparing alcohol and phenol through aerobic hydroxylation reaction of a boric acid derivative in the absence of a photocatalyst, wherein the boric acid derivativeis aryl boronic acid or alkyl boronic acid, and the corresponding target compounds are respectively a phenol-based compound and an alcohol-based compound. According to the method, by using a boric acid derivative as a reaction substrate, an additive is added under a solvent condition, and a hydroxylation reaction is performed under aerobic and illumination conditions to obtain a corresponding target compound. According to the invention, the new strategy is provided for the synthesis of phenols through aerobic hydroxylation of aryl boronic acid without a photocatalyst; the catalyst-free aerobic hydroxylation method for photocatalysis of aryl boronic acid or alkyl boronic acid by using triethylamine as an additive is firstly disclosed; and the new method has advantages of photocatalyst-freecondition, wide substrate range and good functional group compatibility.
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Paragraph 0025-0028; 0030-0032

(2020/01/25)

A Structure-Reactivity Relationship of the Tandem Asymmetric Dihydroxylation on a Biologically Relevant Diene: Influence of Remote Stereocenters on Diastereofacial Selectivity
The Sharpless asymmetric dihydroxylation (AD) finds widespread use in natural product and drug molecule syntheses, in part, due to its efficiency and predictability. However, the tandem AD of dienes is much less studied, but important in complex molecular synthesis. Herein, a biologically relevant tandem AD is reported, and several anomalies are discovered with the accepted model. These include the formation of unpredicted diastereoisomers, with matched and mismatched stereocenters contradicting the Sharpless mnemonic device. From a structural analysis of the tandem AD, we present a strategy to improve asymmetric induction in sterically hindered alkenes using double diastereodifferentiation from a 9-bond distant stereocenter. A theoretical justification for the unpredicted stereoselectivity, accounting for the influence of steric hindrance and pre-installed chirality, is proposed.
Gill, Daniel M.,Male, Louise,Jones, Alan M.
supporting information
p. 7568 - 7577
(2019/12/11)

Synthesis and biological activities of benzothiazole derivatives bearing a 1,3,4-thiadiazole moiety
A series of benzothiazole derivatives bearing a 1,3,4-thiadiazole moiety were designed, synthesized and evaluated for their antibacterial, antifungal and antiviral activities. The bioassay results indicated that most of target compounds showed good antiviral activities against tobacco mosaic virus (TMV) and antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (Rs). Especially, the anti-Xoo effect of title compounds 5k (N-(5-methoxybenzo[d]thiazol-2-yl)-2-((5-(2-tolyl)-1,3,4-thiadiazol-2-yl)thio)acetamide) and the anti-Rs effect of title compounds 5a (N-(5-nitrobenzo[d]thiazol-2-yl)-2-((5-(4-(trifluorom ethyl)phenyl)-1,3,4-thiadiazol-2-yl)thio)acetmide) respectively reached 52.4% and 71.6% at 100 μg/mL, which are superior to that of bismerthiazol (32.0% and 52.3%). In addition, the protective and inactivation activities of title compound 5i (N-(5-methoxybenzo [d]thiazol-2-yl)-2-((5-(4-nitrophenyl)-1,3,4-thiadiazol-2-yl)thio)acetamide) against TMV were 79.5% and 88.3%, respectively, which are better than that of ningnanmycin (76.4% and 86.8%). The above research showed that benzothiazole derivatives bearing a 1,3,4-thiadiazole moiety may be used as potential molecular templates in searching for highly-efficient antiviral and antibacterial agents.
Tang, Xu,Wang, Zhongbo,Zhong, Xinmin,Wang, Xiaobin,Chen, Lijuan,He, Ming,Xue, Wei
p. 241 - 248
(2019/01/04)

Halogen-substituted triazolethioacetamides as a potent skeleton for the development of metallo-β-lactamase inhibitors
Metallo-β-lactamases (MβLs) are the target enzymes of β-lactam antibiotic resistance, and there are no effective inhibitors against MβLs available for clinic so far. In this study, thirteen halogen-substituted triazolethioacetamides were designed and synthesized as a potent skeleton of MβLs inhibitors. All the compounds displayed inhibitory activity against ImiS with an IC50 value range of 0.032–15.64 μM except 7. The chlorine substituted compounds (1, 2 and 3) inhibited NDM-1 with an IC50 value of less than 0.96 μM, and the fluorine substituted 12 and 13 inhibited VIM-2 with IC50 values of 38.9 and 2.8 μM, respectively. However, none of the triazolethioacetamides exhibited activity against L1 at inhibitor concentrations of up to 1 mM. Enzyme inhibition kinetics revealed that 9 and 13 are mixed inhibitors for ImiS with Ki values of 0.074 and 0.27μM using imipenem as the substrate. Docking studies showed that 1 and 9, which have the highest inhibitory activity against ImiS, fit the binding site of CphA as a replacement of ImiS via stable interactions between the triazole group bridging ASP120 and hydroxyl group bridging ASN233.
Zhang, Yilin,Yan, Yong,Liang, Lufan,Jiefeng,Wang, Xuejun,Li, Li,Yang, Kewu
(2019/04/03)

Evaluation of novel N′-(3-hydroxybenzoyl)-2-oxo-2H-chromene-3-carbohydrazide derivatives as potential HIV-1 integrase inhibitors
In an attempt to identify potential new agents that are active against HIV-1 IN, a series of novel coumarin-3-carbohydrazide derivatives were designed and synthesised. The toxicity profiles of these compounds showed that they were non-toxic to human cells and they exhibited promising anti-HIV-1 IN activities with IC50 values in nM range. Also, an accompanying molecular modeling study showed that the compounds bind to the active pocket of the enzyme.
Jesumoroti, Omobolanle J.,Faridoon,Mnkandhla, Dumisani,Isaacs, Michelle,Hoppe, Heinrich C.,Klein, Rosalyn
p. 80 - 88
(2019/01/30)

Design, synthesis, and preliminary biological evaluation of 3′,4′,5′-trimethoxy flavonoid salicylate derivatives as potential anti-tumor agents
According to the pharmacophore combination principle, a set of new 3′,4′,5′-trimethoxy flavonoid salicylate derivatives were designed, synthesized, and evaluated for biological activity. The cytotoxicity evaluation revealed that compound 10v exhibited higher potency than 5-Fu against HCT-116 cells. Preliminary biological activity studies showed that compound 10v could inhibit the colony formation and migration of HCT-116 cells. Besides, the Hoechst 33258 staining assay and flow cytometry revealed that treatment with compound 10v induced the apoptosis of HCT-116 cells in a concentration-dependent manner, while it had no effect on their cell cycle. The WB analysis suggested that HIF-1α, tubulin, HK-2, and PFK might be the potential pharmacophore targets of compound 10v. Tubulin was a potential drug target for compound 10v, which was explained by analyzing the crystal structure of compound 10v complexed with tubulin. These results indicated that compound 10v might be a promising anti-tumor agent candidate, deserving further optimization and evaluation.
Deng, Xiangping,Liu, Renbo,Li, Junjian,Li, Zhongli,Liu, Juan,Xiong, Runde,Lei, Xiaoyong,Zheng, Xing,Xie, Zhizhong,Tang, Guotao
p. 1874 - 1884
(2019/01/28)

Microwave-Assisted Synthesis of Benzofuran-3(2H)-ones
A new method for the synthesis of benzofuran-3(2H)-ones under microwave conditions was developed. The reaction conditions were screened, and the scope of benzoate substrates was investigated. The results showed that our method could provide rapid access to these important dihydrobenzofuranones in 43% to 58% yields.
Hu, Xiaojing,Lai, Huimin,Zhao, Fangfei,Hu, Shuyu,Sun, Qianqian,Fang, Lizhen
p. 745 - 750
(2019/10/14)

Pd(OAc)2-catalyzed orthogonal synthesis of 2-hydroxybenzoates and substituted cyclohexanones from acyclic unsaturated 1,3-carbonyl compounds
A Pd-catalyzed orthogonal synthesis of substituted 2-hydroxybenzoates and substituted cyclohexanones was developed for the first time. The substituted 2-hydroxybenzoates were obtained from acyclic unsaturated 1,3-carbonyl compounds using a combination of catalytic Pd(OAc)2 and Cu(OAc)2. On the other hand, the substituted cyclohexanones were produced from similar substrates via catalytic Pd(OAc)2 and hydrogen chloride. Each transformation was clean, easy to work up, provided the desired compounds in good purities, and did not require column chromatography purification.
Miyagi, Toshinori,Okada, Sho,Tada, Naoya,Sugihara, Masahiro,Kagawa, Natsuko,Takabatake, Tetsuhiko,Toyota, Masahiro
supporting information
p. 1653 - 1657
(2019/05/29)

Photoinduced hydroxylation of arylboronic acids with molecular oxygen under photocatalyst-free conditions
Photoinduced hydroxylation of boronic acids with molecular oxygen under photocatalyst-free conditions is reported, providing a green entry to a variety of phenols and aliphatic alcohols in a highly concise fashion. This new protocol features photocatalyst-free conditions, wide substrate scope and excellent functional group compatibility.
Xu, Yu-Ting,Li, Chen-Yuan,Huang, Xiao-Bo,Gao, Wen-Xia,Zhou, Yun-Bing,Liu, Miao-Chang,Wu, Hua-Yue
supporting information
p. 4971 - 4975
(2019/09/30)

P-Methylbenzyl Group: Oxidative Removal and Orthogonal Alcohol Deprotection
We describe the practical removal of p-methylbenzyl (MBn) protections of alcohols by treatment with 2,3-dichloro-5,6-dicyano-p-benzoquinone. When a molecule bears benzyl and MBn groups, the oxidant selectively removes the latter groups. Further, the MBn groups tolerate ceric ammonium nitrate, resulting in chemoselective removal of the p-methoxybenzyl group in the presence of the MBn groups. These orthogonal alcohol deprotections would provide novel synthetic strategies of organic compounds.
Ikeuchi, Kazutada,Murasawa, Kentaro,Ohara, Kenya,Yamada, Hidetoshi
supporting information
p. 6638 - 6642
(2019/09/30)

Pd-Colloids-Catalyzed/Ag2O-Oxidized General and Selective Esterification of Benzylic Alcohols
Palladium colloids obtained from the degradation of Hermann–Beller palladacycle proved to be an efficient catalytic system in combination with silver oxide as a selective oxidant for the oxidative esterification of differently substituted benzyl alcohols in MeOH as solvent. Excellent reactivity exhibited by the catalytic system also allowed the alcoholic coupling partner to be changed from MeOH to a wide range of alcohols having diverse functionalities. The mildness of the developed protocol also made it possible to employ propargyl alcohol as the coupling partner without any observation of any interference of the terminal alkyne. Selective oxidative coupling of a primary alcoholic functional group over secondary in the case of glycols and glycerols was also made possible using the developed catalyst system. To test the relevancy of Pd/Ag combined catalysis mixed Pd/Ag colloids were synthesized, characterized by TEM, XRD and XPS and applied to oxidative-esterification successfully.
Sable, Vaibhav,Shah, Jagrut,Sharma, Anuja,Kapdi, Anant R.
supporting information
p. 2639 - 2647
(2019/07/08)

Benzoheterocycle-carboxamide-pyridone derivatives and preparation method and applications thereof
The invention belongs to the field of chemical medicine preparation, and concretely relates to benzoheterocycle-carboxamide-pyridone derivatives, a preparation method and applications thereof. The invention provides the benzoheterocycle-carboxamide-pyridone derivatives, and a structure is represented by a formula I. The present invention also provides the preparation method and the applications ofthe above benzoheterocycle-carboxamide-pyridone derivatives. The benzoheterocycle-carboxamide-pyridone derivatives provided by the invention are novel compounds obtained on the basis of a large number of screening, inhibit EZH2 activity, and provide a novel selection for development and application of medicines for resisting tumors and autoimmune diseases.
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Paragraph 0090; 0091; 0092

(2018/03/26)

Synthesis, structure and in vitro cytotoxicity testing of some 1,3,4-oxadiazoline derivatives from 2-hydroxy-5-iodobenzoic acid
The syntheses of nine new 5-iodosalicylic acid-based 1,3,4-oxadiazoline derivatives starting from methyl salicylate are described. These compounds are 2-[4-acetyl-5-methyl-5-(3-nitrophenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4- iodophenyl acetate (6a), 2-[4-acetyl-5-methyl-5-(4-nitrophenyl)-4,5-dihydro- 1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6b), 2-(4-acetyl-5-methyl-5-phenyl- 4,5-dihydro-1,3,4-oxadiazol-2-yl)-4-iodophenyl acetate, C19H17IN2O4 (6c), 2-[4-acetyl-5-(4-fluorophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate, C19H16FIN2O4 (6d), 2-[4-acetyl-5-(4-chlorophenyl)-5-methyl- 4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate, C19H16ClIN2O4 (6e), 2-[4-acetyl-5-(3-bromophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6f), 2-[4-acetyl-5-(4-bromophenyl)-5-methyl-4,5-dihydro-1,3,4- oxadiazol-2-yl]-4-iodophenyl acetate (6g), 2-[4-acetyl-5-methyl-5-(4-methylphenyl)- 4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6h) and 2-[5-(4- acetamidophenyl)-4-acetyl-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6i). The compounds were characterized by mass,1H NMR and13C NMR spectroscopies. Single-crystal X-ray diffraction studies were also carried out for 6c, 6d and 6e. Compounds 6c and 6d are isomorphous, with the 1,3,4-oxadiazoline ring having an envelope conformation, where the disubstituted C atom is the flap. The packing is determined by C—H…O, C—H…and I…π interactions. For 6e, the 1,3,4-oxadiazoline ring is almost planar. In the packing, Cl…π interactions are observed, while the I atom is not involved in short interactions. Compounds 6d, 6e, 6f and 6h show good inhibiting abilities on the human cancer cell lines KB and Hep-G2, with IC50 values of 0.9-4.5 μM.
Nguyen Tien, Cong,Nguyen Van, Thin,Le Duc, Giang,Vu Quoc, Manh,Vu Quoc, Trung,Pham Chien, Thang,Nguyen Huy, Hung,Dang Thi Tuyet, Anh,Nguyen Van, Tuyen,Van Meervelt, Luc
p. 839 - 846
(2018/07/15)

Structure-Guided Synthesis and Mechanistic Studies Reveal Sweetspots on Naphthyl Salicyl Hydrazone Scaffold as Non-Nucleosidic Competitive, Reversible Inhibitors of Human Ribonucleotide Reductase
Ribonucleotide reductase (RR), an established cancer target, is usually inhibited by antimetabolites, which display multiple cross-reactive effects. Recently, we discovered a naphthyl salicyl acyl hydrazone-based inhibitor (NSAH or E-3a) of human RR (hRR) binding at the catalytic site (C-site) and inhibiting hRR reversibly. We herein report the synthesis and biochemical characterization of 25 distinct analogs. We designed each analog through docking to the C-site of hRR based on our 2.7 ? X-ray crystal structure (PDB ID: 5TUS). Broad tolerance to minor structural variations preserving inhibitory potency is observed. E-3f (82% yield) displayed an in vitro IC50 of 5.3 ± 1.8 μM against hRR, making it the most potent in this series. Kinetic assays reveal that E-3a, E-3c, E-3t, and E-3w bind and inhibit hRR through a reversible and competitive mode. Target selectivity toward the R1 subunit of hRR is established, providing a novel way of inhibition of this crucial enzyme.
Huff, Sarah E.,Mohammed, Faiz Ahmad,Yang, Mu,Agrawal, Prashansa,Pink, John,Harris, Michael E.,Dealwis, Chris G.,Viswanathan, Rajesh
supporting information
p. 666 - 680
(2018/02/16)

Gold promoted arylative cyclization of alkynoic acids with arenediazonium salts
Alkynoic acids derived from salicylic acid and analogues undergo arylative cyclization with arenediazonium salts promoted by gold in the absence of external ligands. The reaction is thermally induced and proceeds even in the absence of light. A difference in regioselectivity has been found compared with that observed in the cycloisomerization process of the same type of compounds.
Carrillo-Arcos, Ulises A.,Porcel, Susana
supporting information
p. 1837 - 1842
(2018/03/23)

Structural design, synthesis and substituent effect of hydrazone-N-acylhydrazones reveal potent immunomodulatory agents
4-(Nitrophenyl)hydrazone derivatives of N-acylhydrazone were synthesized and screened for suppress lymphocyte proliferation and nitrite inhibition in macrophages. Compared to an unsubstituted N-acylhydrazone, active compounds were identified within initial series when hydroxyl, chloride and nitro substituents were employed. Structure-activity relationship was further developed by varying the position of these substituents as well as attaching structurally-related substituents. Changing substituent position revealed a more promising compound series of anti-inflammatory agents. In contrast, an N-methyl group appended to the 4-(nitrophenyl)hydrazone moiety reduced activity. Anti-inflammatory activity of compounds is achieved by modulating IL-1β secretion and prostaglandin E2 synthesis in macrophages and by inhibiting calcineurin phosphatase activity in lymphocytes. Compound SintMed65 was advanced into an acute model of peritonitis in mice, where it inhibited the neutrophil infiltration after being orally administered. In summary, we demonstrated in great details the structural requirements and the underlying mechanism for anti-inflammatory activity of a new family of hydrazone-N-acylhydrazone, which may represent a valuable medicinal chemistry direction for the anti-inflammatory drug development in general.
Meira, Cássio S.,dos Santos Filho, José Maurício,Sousa, Caroline C.,Anjos, Pamela S.,Cerqueira, Jéssica V.,Dias Neto, Humberto A.,da Silveira, Rafael G.,Russo, Helena M.,Wolfender, Jean-Luc,Queiroz, Emerson F.,Moreira, Diogo R.M.,Soares, Milena B.P.
p. 1971 - 1985
(2018/03/12)

A biocatalytic method for the chemoselective aerobic oxidation of aldehydes to carboxylic acids
Herein, we present a study on the oxidation of aldehydes to carboxylic acids using three recombinant aldehyde dehydrogenases (ALDHs). The ALDHs were used in purified form with a nicotinamide oxidase (NOx), which recycles the catalytic NAD+ at the expense of dioxygen (air at atmospheric pressure). The reaction was studied also with lyophilised whole cell as well as resting cell biocatalysts for more convenient practical application. The optimised biocatalytic oxidation runs in phosphate buffer at pH 8.5 and at 40 °C. From a set of sixty-one aliphatic, aryl-Aliphatic, benzylic, hetero-Aromatic and bicyclic aldehydes, fifty were converted with elevated yield (up to >99%). The exceptions were a few ortho-substituted benzaldehydes, bicyclic heteroaromatic aldehydes and 2-phenylpropanal. In all cases, the expected carboxylic acid was shown to be the only product (>99% chemoselectivity). Other oxidisable functionalities within the same molecule (e.g. hydroxyl, alkene, and heteroaromatic nitrogen or sulphur atoms) remained untouched. The reaction was scaled for the oxidation of 5-(hydroxymethyl)furfural (2 g), a bio-based starting material, to afford 5-(hydroxymethyl)furoic acid in 61% isolated yield. The new biocatalytic method avoids the use of toxic or unsafe oxidants, strong acids or bases, or undesired solvents. It shows applicability across a wide range of substrates, and retains perfect chemoselectivity. Alternative oxidisable groups were not converted, and other classical side-reactions (e.g. halogenation of unsaturated functionalities, Dakin-Type oxidation) did not occur. In comparison to other established enzymatic methods such as the use of oxidases (where the concomitant oxidation of alcohols and aldehydes is common), ALDHs offer greatly improved selectivity.
Knaus, Tanja,Tseliou, Vasilis,Humphreys, Luke D.,Scrutton, Nigel S.,Mutti, Francesco G.
p. 3931 - 3943
(2018/09/11)

Palladium-Catalyzed Aerobic Oxidative Carbonylation of C–H Bonds in Phenols for the Synthesis of p-Hydroxybenzoates
This work reports the synthesis of p-hydroxybenzoates directly from phenols by oxidative carbonylation of phenolic C–H bonds, proceding through oxidative iodination. The developed methodology is efficient and economically attractive because phenols are cheap and easily available starting materials. This one-pot strategy was expediently applied to the synthesis of a variety of p-hydroxybenzoates by utilizing simple primary and secondary alcohols with different phenols under mild reaction conditions. Advantageously, the procedure has no need for co-catalysts, co-solvents or external ligands. The utilization of molecular oxygen as a terminal oxidant for C–H bond oxidation represents an additional benefit.
Gaikwad, Vinayak V.,Bhanage, Bhalchandra M.
supporting information
p. 2877 - 2881
(2018/06/21)

One-Step O -Demethyl-Decarboxylation of ortho -Methoxy Aromatic Carboxylic Acids
A highly selective decarboxydemethylation of o -methoxyarenecarboxylic acids is described. The reaction takes place in DMPU at 170 °C in the presence of TMEDA and iron powder. A similar reaction has not been reported until now.
Cahiez, Gérard,Moyeux, Alban,Zhou, Edouard,Poizat, Ma?l
p. 2119 - 2123
(2018/04/12)

A convenient synthesis of phenols
Anilines are rapidly, often within 60 minutes, converted into the corresponding phenols in up to 87% isolated yield. The presented experimentally simple protocol display broad compatibility with a variety of functional groups, and in particular, well suited for the preparation of methyl-substituted phenols. Such phenols are not easily available by other synthetic approaches. The formation of phenolic radical coupling products was not observed even for activated anilines using this open flask method.
Kristianslund, Renate,Vik, Anders,Hansen, Trond V.
supporting information
p. 2809 - 2814
(2018/12/04)

Synthesis of Hydroxybenzoic Acids and Their Esters by Reaction of Phenols with Carbon Tetrachloride and Alcohols in the Presence of Iron Catalysts
Alkyl esters of hydroxy-, methoxy-, and ethoxybenzoic and cresotic acids have been synthesized by reaction of phenols, anisole, phenetole, and cresols with carbon tetrachloride and alcohols in the presence of iron catalysts.
Bayguzina,Tarisova,Khusnutdinov
p. 208 - 215
(2018/03/26)

Chemoselective ester/ether C–O cleavage of methyl anisates by aluminum triiodide
The aluminum triiodide mediated chemoselective ester/ether C–O cleavage of methyl anisates was investigated. o-Anisate undergoes ether cleavage at low temperatures in carbon disulfide, cyclohexane and acetonitrile. Further cleavage of the ester group occurs at elevated temperatures to afford salicylic acid. The cleavage of p-anisate is solvent-dependent. In cyclohexane, the ester and ether groups were cleaved non-selectively to give equimolar amounts of p-anisic acid and methyl p-hydroxybenzoate. The ester group was preferentially cleaved in acetonitrile, compared to ether group cleavage in carbon disulfide. The ester cleavage reaction was improved using pyridine as an acid scavenger additive. Reasons for the contrasting reactivity of anisates towards AlI3 were explored, and the methods were applied to cleavage of the tert-butyl ester of acemetacin which gave different products under these conditions.
Sang, Dayong,Yi, Cuicui,He, Zhoujun,Wang, Jiahui,Tian, Juan,Yao, Ming,Shi, Hong
supporting information
p. 1469 - 1472
(2018/03/13)

Benzo wicked zuozuo apperception compound and its preparation and use
The invention provides a benzoxazole compound. The structure of the benzoxazole compound is shown in the formula (I), wherein R1, R2, R3 and R4 are hydrogen, C1-C5 alkyl, benzyl, aryl or hetero aryl. The preparation method of the benzoxazole compound is carried out according to the following reaction route. Compared with the prior art, the benzoxazole compound has the benefits that the Sortase A protease of bacteroid is used as a target spot, a similar structure of a Sortase A substrate is constructed through the action mechanism of the known Sortase A and the cell wall of a host cell, and new compounds with benzoxazole and mother nucleus are synthesized; the new compounds carry out the test screening of Sortase A activity inhibition so as to try to find candidate compounds for effectively inhibiting staphylococcus aureus infection.
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Paragraph 0040-0042

(2017/10/27)

Zirconocene-catalyzed direct (trans)esterification of acyl acids (esters) and alcohols in a strict 1:1 ratio under solvent-free conditions
A highly efficient way for the direct (trans)esterification of acyl acids (esters) and alcohols in a strict 1:1 ratio using a zirconocene complex (1, 1 mol%), a strong Lewis acid of good water tolerance, as a catalyst under solvent-free conditions has been developed. A wide range of acid and alcohol (esters) substrates undergo (trans)esterification to produce carboxylic ester motifs in moderate to good or excellent yields with good functional tolerance, such as that towards C-Br as well as CC and CC bonds. And complex 1 can be recycled six times without showing a significant decline in catalytic efficiency. It was demonstrated that cyclandelate, which is used to treat high blood pressure as well as heart and blood-vessel diseases, can be directly synthesized on a gram scale with 81% yield (6.70 g) using complex 1.
Tang, Zhi,Jiang, Qiutao,Peng, Lifen,Xu, Xinhua,Li, Jie,Qiu, Renhua,Au, Chak-Tong
supporting information
p. 5396 - 5402
(2017/11/22)

Chemical Properties

Appearance/Colour :colourless liquid with an odour of wintergreen
Melting Point: -8 °C
Boiling Point: 222 °C at 760 mmHg
Flash Point:86.8 °C
Density: 1.209 g/cm³
Solubility:Very slightly soluble in water, miscible with ethanol (96 per cent) and with fatty and essential oils.
Storage Temp.:Inert atmosphere,Room Temperature
Vapor Density: 5.26 (vs air)
Vapor Pressure: 1 mm Hg ( 54 °C)
Refractive Index: 1.535 - 1.538
PKA: pKa 9.90 (Uncertain)
Merck: 14,6120
BRN: 971516
PSA: 46.53000
LogP: 1.17880

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Article Database

119-36-8

Articles about 119-36-8Total 218 be found

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Chemical Properties

Appearance/Colour :colourless liquid with an odour of wintergreen

Melting Point: -8 °C

Boiling Point: 222 °C at 760 mmHg

Flash Point:86.8 °C

Density: 1.209 g/cm³

Solubility:Very slightly soluble in water, miscible with ethanol (96 per cent) and with fatty and essential oils.

Storage Temp.:Inert atmosphere,Room Temperature

Vapor Density: 5.26 (vs air)

Vapor Pressure: 1 mm Hg ( 54 °C)

Refractive Index: 1.535 - 1.538

PKA: pKa 9.90 (Uncertain)

Merck: 14,6120

BRN: 971516

PSA: 46.53000

LogP: 1.17880

Global suppliers and manufacturers of 119-36-8total 309 suppliers on LookChem

Article Database

119-36-8

Articles about 119-36-8Total 218 be found

More Articles about upstream products of 119-36-8

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Chemical Properties

Appearance/Colour :colourless liquid with an odour of wintergreen

Melting Point: -8 °C

Boiling Point: 222 °C at 760 mmHg

Flash Point:86.8 °C

Density: 1.209 g/cm3

Solubility:Very slightly soluble in water, miscible with ethanol (96 per cent) and with fatty and essential oils.

Storage Temp.:Inert atmosphere,Room Temperature

Vapor Density: 5.26 (vs air)

Vapor Pressure: 1 mm Hg ( 54 °C)

Refractive Index: 1.535 - 1.538

PKA: pKa 9.90 (Uncertain)

Merck: 14,6120

BRN: 971516

PSA: 46.53000

LogP: 1.17880

Global suppliers and manufacturers of 119-36-8total 309 suppliers on LookChem

Density: 1.209 g/cm³