cas 881-90-3, 2-methyl-4-(phenylmethylene)oxazol-5(4H)-one

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Synthesis of series of low band gap small organic molecules and evaluation of their solar cell activity
Organic solar cells have attracted much attention in the recent years but still in search of devices with efficiency comparable to that of silicon solar cells. In this view, a series of highly conjugated imidazolinone molecules were synthesized by a simple in situ coupling method, which resulted in high yield (85-95 %) of the products compared to the traditional method of synthesis. UV-visible studies performed in varying solvents differing in polarity, showing shift in their spectra with change in polarity. The band gap calculated thereafter ranged between 2.8-3.1 eV showing their potential for use in photovoltaic cell. Studies of the I-V characteristics of the photovoltaic devices fabricated with the newly synthesized molecules were performed. The devices with naphthalene substituent showed the highest power conversion efficiency of 0.1 % compared to others, thereby opening up room for use in organic solar cells.
Sharma,Handique
p. 2223 - 2227
(2016)
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Synthesis, in silico prediction and in vitro evaluation of antimicrobial activity, dft calculation and theoretical investigation of novel xanthines and uracil containing imidazolone derivatives
Novel xanthine and imidazolone derivatives were synthesized based on oxazolone derivatives 2a-c as a key intermediate. The corresponding xanthine 3-5 and imidazolone derivatives 6-13 were obtained via reaction of oxazolone derivative 2a-c with 5,6-diaminouracils 1a-e under various conditions. Xanthine compounds 3-5 were obtained by cyclocondensation of 5,6-diaminouracils 1a-c with different oxazolones in glacial acetic acid. Moreover, 5, 6-diaminouracils 1a-e were reacted with oxazolones 2a-c in presence of drops of acetic acid under fused condition yielding the imidazolone derivatives 6-13. Furthermore, Schiff base of compounds 14-16 were obtained by condensing 5, 6-diaminouracils 1a,b,e with 4-dimethylaminobenzaldehyde in acetic acid. The structural identity of the resulting compounds was resolved by IR,1H-,13C-NMR and Mass spectral analyses. The novel synthesized compounds were screened for their antifungal and antibacterial activities. Compounds 3, 6, 13 and 16 displayed the highest activity against Escherichia coli as revealed from the IC50 values (1.8–1.9 μg/mL). The compound 16 displayed a significant antifungal activity against Candia albicans (0.82 μg/mL), Aspergillus flavus (1.2 μg/mL) com-paring to authentic antibiotics. From the TEM microgram, the compounds 3, 12, 13 and 16 exhib-ited a strong deformation to the cellular entities, by interfering with the cell membrane compo-nents, causing cytosol leakage, cellular shrinkage and irregularity to the cell shape. In addition, docking study for the most promising antimicrobial tested compounds depicted high binding affinity against acyl carrier protein domain from a fungal type I polyketide synthase (ACP), and Baumannii penicillin-binding protein (PBP). Moreover, compound 12 showed high drug-likeness, and excellent pharmacokinetics, which needs to be in focus for further antimicrobial drug devel-opment. The most promising antimicrobial compounds underwent theoretical investigation using DFT calculation.
El-Kalyoubi, Samar,Agili, Fatimah,Zordok, Wael A.,El-Sayed, Ashraf S. A.
(2021/10/14)

2H-thiazolo [3, 2-b]-1, 2, 4-triazine-3, 7-diketone derivative and application thereof
The invention discloses a 2Hthiazolo [3, 2b] 1, 2, 4triazine 3, 7diketone derivative as shown in a general formula I or pharmaceutically acceptable hydrate and salt thereof, the 2Hthiazolo [3, 2b] 1,2, 4triazine 3, 7diketone derivative comprises stereoisomers or tautomers thereof, and R1 and R2 in the general formula I can be optionally selected from one, two or three independently selected fromhydrogen, alkyl, alkoxy, halogen, hydroxyl, acetyl, propionyl, nitro or trifluoromethyl. The 1, 2, 4-triazine 3, 7diketone derivative has an obvious inhibiting effect on acetylcholin esterase, and isused for enhancing the memory of a patient suffering from dementia and Alzheimer's disease. The invention also relates to a preparation method of the compound and the application of the compound in preparation of drugs for treating Alzheimer's disease.
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(2020/12/29)

Activated carbon/Br?nsted acid-promoted aerobic benzylic oxidation under “on-water” condition: Green and efficient synthesis of 3-benzoylquinoxalinones as potent tubulin inhibitors
Green chemistry is becoming the favored approach to preparing drug molecules in pharmaceutical industry. Herein, we developed a clean and efficient method to synthesize 3-benzoylquinoxalines via activated carbon promoted aerobic benzylic oxidation under “on-water” condition. Moreover, biological studies with this class of compounds reveal an antiproliferative profile. Further structure modifications are performed and the investigations exhibited that the most active 12a could inhibit the microtubule polymerization by binding to tubulin and thus induce multipolar mitosis, G2/M phase arrest, and apoptosis of cancer cells. In addition, molecular docking studies allow the rationalization of the pharmacodynamic properties observed. Our systematic studies provide not only guidance for applications of O2/AC/H2O system, but also a new scaffold targeting tubulin for antitumor agent discovery.
Guan, Qi,Cong, Lin,Wang, Qing,Yu, Changyue,Bao, Kai,Zhou, Kai,Wu, Lan,Zhang, Weige
supporting information

(2019/12/06)

Nickel-Catalyzed Asymmetric Hydrogenation of 2-Amidoacrylates
Earth-abundant nickel, coordinated with a suitable chiral bisphosphine ligand, was found to be an efficient catalyst for the asymmetric hydrogenation of 2-amidoacrylates, affording the chiral α-amino acid esters in quantitative yields and excellent enantioselectivity (up to 96 % ee). The active catalyst component was studied by NMR and HRMS, which helped us to realize high catalytic efficiency on a gram scale with a low catalyst loading (S/C=2000). The hydrogenated products could be simply converted into chiral α-amino acids, β-amino alcohols, and their bioactive derivatives. Furthermore, the catalytic mechanism was investigated using deuterium-labeling experiments and computational calculations.
Chen, Jianzhong,Gridnev, Ilya D.,Hu, Yawen,Li, Bowen,Zhang, Wanbin,Zhang, Zhenfeng
supporting information
p. 5371 - 5375
(2020/02/15)

Topology-Based Functionalization of Robust Chiral Zr-Based Metal-Organic Frameworks for Catalytic Enantioselective Hydrogenation
The design and development of robust and porous supported catalysts with high activity and selectivity is extremely significant but very challenging for eco-friendly synthesis of fine chemicals and pharmaceuticals. We report here the design and synthesis of highly stable chiral Zr(IV)-based MOFs with different topologies to support Ir complexes and demonstrate their network structures-dependent asymmetric catalytic performance. Guided by the modulated synthesis and isoreticular expansion strategy, five chiral Zr-MOFs with a flu or ith topology are constructed from enantiopure 1,1′-biphenol-derived tetracarboxylate linkers and Zr6, Zr9, or Zr12 clusters. The obtained MOFs all show high chemical stability in boiling water, strongly acidic, and weakly basic aqueous solutions. The two flu MOFs featuring the dihydroxyl groups of biphenol in open and large cages, after sequential postsynthetic modification with P(NMe2)3 and [Ir(COD)Cl]2, can be highly efficient and recyclable heterogeneous catalysts for hydrogenation of α-dehydroamino acid esters with up to 98% ee, whereas the three ith MOFs featuring the dihydroxyl groups in small cages cannot be installed with P(NMe2)3 to support the Ir complex. Incorporation of Ir-phosphorus catalysts into Zr-MOFs leads to great enhancement of their chemical stability, durability, and even stereoselectivity. This work therefore not only advances Zr-MOFs as stable supports for labile metal catalysts for heterogeneous asymmetric catalysis but also provides a new insight into how highly active chiral centers can result due to the framework topology.
Jiang, Hong,Zhang, Wenqiang,Kang, Xing,Cao, Ziping,Chen, Xu,Liu, Yan,Cui, Yong
supporting information
p. 9642 - 9652
(2020/07/02)

Scope and limitations of reductive amination catalyzed by half-sandwich iridium complexes under mild reaction conditions
The conversion of aldehydes and ketones to 1° amines could be promoted by half-sandwich iridium complexes using ammonium formate as both the nitrogen and hydride source. To optimize this method for green chemical synthesis, we tested various carbonyl substrates in common polar solvents at physiological temperature (37 °C) and ambient pressure. We found that in methanol, excellent selectivity for the amine over alcohol/amide products could be achieved for a broad assortment of carbonyl-containing compounds. In aqueous media, selective reduction of carbonyls to 1° amines was achieved in the absence of acids. Unfortunately, at Ir catalyst concentrations of 1 mM in water, reductive amination efficiency dropped significantly, which suggest that this catalytic methodology might be not suitable for aqueous applications where very low catalyst concentration is required (e.g., inside living cells).
Nguyen, Dat P.,Sladek, Rudolph N.,Do, Loi H.
supporting information

(2020/07/15)

Silver-Promoted Direct Phosphorylation of Bulky C(sp2)-H Bond to Build Fully Substituted β-Phosphonodehydroamino Acids
A general and practical cross-dehydrogenative coupling protocol between readily available trisubstituted α,β-dehydro α-amino carboxylic esters and H-phosphites is described. This C(sp2)-H phosphorylation reaction proceeds with absolute Z-selectivity promoted by silver salt in a radical relay manner. The bulky tetrasubstituted β-phosphonodehydroamino acids were obtained in grams and added new modules to the toolkit for peptide modifications.
Cao, Hao-Qiang,Liu, Hao-Nan,Liu, Zhe-Yuan,Qiao, Baokun,Zhang, Fa-Guang,Ma, Jun-An
supporting information
p. 6414 - 6419
(2020/09/02)

Synthesis and biological evaluation of imidazoline derivatives as potential CNS and CVS agents
A series of substituted imidazoline derivatives were synthesized and characterized. Compounds were tested in-vivo for their antihypertensive, analgesic, antiaggressive, depressant, antidepressant, and ALD50 activities. The compounds 3a, 3c, 4c, 5a, and 6c showed cardiovascular as well as central nervous system activities and are potential candidate as drug among all fifteen compounds tested. All these compounds have shown better activity for antihypertensive, analgesic, antiaggressive, and depressant-antidepressant, properties than reference compounds clonidine, morphine, diazepam, and imipramine respectively. Most of the compounds have shown ALD50 > 500 mg/kg with maximum in 4a and 5a (>1000 mg/kg).
Malhotra, Vineet,Vats, Monika,Nath, Rajendra,Mehta, Simpi,Kumar, Rakesh,Bhalla, Manish,Sinha,Shanker,Pathak, Seeema R.
supporting information

(2020/10/21)

Synthesis of the Natural Product Iotrochamide B
Iotrochamide B is the first cinnamoyl amino acid reported from the marine sponge Iotrochota sp. The total synthesis of the marine indole alkaloid iotrochamide B was achieved by condensation of 6-bromo-L-tryptophan (3) and (Z)-2-methoxy-3-phenylacrylic acid (6). The key step was the synthesis of 6-bromo-L-tryptophan ((S)-3) from racemic N-acetyltryptophan by optical resolution using (S)-(–)-1-phenylethylamine. This work provides an efficient method for future synthesis of iotrochamide B derivatives.
Wang,Zhao,Que
p. 499 - 501
(2019/07/02)

Chiral bisphosphine ligands based on quinoline oligoamide foldamers: application in asymmetric hydrogenation
A series of chiral bisphosphine ligands were designed and synthesized based on single-handed quinoline oligoamide foldamers. The bisphosphine ligands can coordinate with Rh(cod)2BF4 in a 1 : 1 stoichiometry and the resulted chiral Rh(i) catalysts were applied in the asymmetric hydrogenation of α-dehydroamino acid esters, in which excellent conversions and promising levels of enantioselectivity were achieved.
Zheng, Lu,Zheng, Dan,Wang, Yanru,Yu, Chengyuan,Zhang, Kun,Jiang, Hua
supporting information
p. 9573 - 9577
(2019/11/20)

METHOD OF SCREENING FOR AGENTS FOR DIFFERENTIATING STEM CELLS
The present application discloses a method for identifying an agent for the treatment or prevention of cancer or metastatic cancer comprising the steps of contacting stem cell with a potential agent, and identifying an agent that induces differentiation, or inhibits stem cell pluripotency or growth of the stem cell, wherein such agent is determined to be an anti-cancer agent.
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(2018/11/02)

Synthesis, β-catenin translocation capability and ALP activation activity of 7h-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives
Background: Osteoporosis (OP) is a common bone disease, most often diagnosed in post-menopausal women. The majority of OP treatments are focused on manipulation of the patient's hormone levels, therefore, they are associated with significant adverse effects. Objective: The study aimed to design, synthesize and evaluate the β-Catenin translocation capability and the alkaline phosphatase (ALP) activation activity of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives. Method: The styrene derivatives were synthesized as raw materials, followed by oxidation and condensation reactions, in which 6-aryl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one derivatives (1) were obtained. The 3,6-diaryl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-ones (2) were obtained by a condensation reaction of compound 1 with substituted phenacyl chlorides in acetic acid. The target compounds 3,6-diaryl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-ones (3a-3c) were prepared by compound 2 with substituted alkyl chloride by Williamson reaction. As to 6-benzyl-3-aryl-7H-thiazolo[3,2- b]-1,2,4-triazin-7-one derivatives as the target compounds, the benzaldehyde and acetylglycine used as raw materials, followed by Erlenmeyer-Pl?chl reaction, condensation reaction, hydrolysis reaction, condensation reaction, 6-benzyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one derivatives were obtained, and were converted to the target compounds 6-benzyl-3-(hydroxylaryl)-7Hthiazolo[ 3,2-b]-1,2,4-triazin-7-one derivatives (5a-5d) using reaction with substituted β-phenacyl chlorides. Finally, Williamson reaction were used to yield 6-benzyl-3-aryl-7H-thiazolo[3,2-b]- 1,2,4-triazin-7-ones as target compounds (6a-6e). The β-Catenin translocation capability and the ALP activation activity were tested, and the glycogen synthase kinase-3 (GSK-3) inhibition was simulated by molecular docking. Results: Fourteen 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives were synthesized and characterized by mass spectra, proton NMR and infrared spectra, the β-Catenin translocation capability and the ALP activation activities of the target compounds were tested and calculated. The EC50 value of the ALP activation activity of 6-(4-chlorobenzyl)-3-{4-[(2-dimethylamino)-2- oxoethoxy]phenyl}-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one (6b) was 11.283 μM. The molecular docking results have showed that the target compounds would be GSK-3 inhibitors. Conclusion: Based on the results of the biological activity test, the target compounds have exhibited the β-Catenin translocation capability and the ALP activation activity.
Hou, Shicheng,Xu, Henan,Hu, Jianshu,Hou, Jian,Wang, Yan,Jin, Zhe,Wan, David C. C.,Hu, Chun
p. 67 - 73
(2018/02/14)

An Atropos Biphenyl Bisphosphine Ligand with 2,2′-tert-Butylmethylphosphino Groups for the Rhodium-Catalyzed Asymmetric Hydrogenation of Enol Esters
This is an update of our previous work concerning the development of Atropos biphenyl bisphosphine ligands. An unexpected Atropos structural property was confirmed by single crystal X-ray diffraction and this result is consistent with the computational calculations described in our previous work. This P-stereogenic bisphosphine ligand possessing a biphenyl backbone and 2,2′-tert-butylmethylphosphino groups has been applied to the Rh-catalyzed asymmetric hydrogenation of enol esters, which has not been widely studied and can be used for the synthesis of several important bioactive compounds. Although there is room for further improvement in enantioselectivity, the results reported herein provide a further understanding of such types of ligands. (Figure presented.).
Jia, Jia,Fan, Dongyang,Zhang, Jian,Zhang, Zhenfeng,Zhang, Wanbin
supporting information
p. 3793 - 3800
(2018/09/20)

Resolving Electronic Transitions in Synthetic Fluorescent Protein Chromophores by Magnetic Circular Dichroism
The detailed electronic structures of fluorescent chromophores are important for their use in imaging of living cells. A series of green fluorescent protein chromophore derivatives is examined by magnetic circular dichroism (MCD) spectroscopy, which allows the resolution of more bands than plain absorption and fluorescence. Observed spectral patterns are rationalized with the aid of time-dependent density functional theory (TDDFT) computations and the sum-over-state (SOS) formalism, which also reveals a significant dependence of MCD intensities on chromophore conformation. The combination of organic and theoretical chemistry with spectroscopic techniques also appears useful in the rational design of fluorescence labels and understanding of the chromophore's properties. For example, the absorption threshold can be heavily affected by substitution on the phenyl ring but not much on the five-member ring, and methoxy groups can be used to further tune the electronic levels.
Cowie, Thomas Y.,?afa?ík, Martin,?ebestík, Jaroslav,Pohl, Radek,Bou?, Petr,?těpánek, Petr
p. 2348 - 2354
(2016/08/27)

Thiazole[3,2-b]-1,2,4-thiazole derivatives and application thereof
The invention belongs to the technical field of medicine and relates to thiazole[3,2-b]-1,2,4-thiazole derivatives and an application thereof. The thiazole[3,2-b]-1,2,4-thiazole derivatives comprise thiazole[3,2-b]-1,2,4-thiazole derivative compounds as well as stereoisomers and pharmaceutically applicable salts of the compounds, and a general structural formula of the compounds is represented in the specification; the thiazole[3,2-b]-1,2,4-thiazole derivatives and the pharmaceutically applicable acid-addition salts of the compounds can be combined with existing drugs or separately utilized to serve as glucose concentration dependent type insulin secretion accelerants for treatment of type II diabetes. Compared with the prior art, the compounds are the glucose concentration dependent type insulin secretion accelerants, can promote insulin secretion under high glucose concentration and do not influence insulin secretion under low glucose concentration, so that the side effect of hypoglycemia is avoided.
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(2018/02/04)

Design, synthesis and biological evaluation of novel 1,2,4-triazolo and 1,2,4-triazino[4,3-a]quinoxalines as potential anticancer and antimicrobial agents
In an effort to find new leads as anticancer or antimicrobial agents, the present work deals with the synthesis of some novel 1-substituted 1,2,4-triazolo[4,3-a]quinoxalines 7, 9a,b, and 14-19 and 1,2,4-triazino[4,3-a]quinoxalines 10a-c as well as 2-[5-amino-3-(4-chlorophenyl)pyrazol-1-yl]-3-benzylquinoxaline 13. These were synthesized using the key intermediate 3-benzyl-2-hydrazinoquinoxaline 6 with various reagents. Ten compounds, namely 7, 9a, 10b, 11, and 13-18 were chosen by the National Cancer Institute of Bethesda (NCI) for evaluation of their anticancer activity. The results indicated that 9a was the most active and was further evaluated for in vitro five dose assay against 60 human cell lines. It was proven to possess the highest broad spectrum anticancer activity. It showed particular effectiveness towards leukemia SR, non-small cell lung cancer HOP-92, NCI-H460, colon cancer HCT-116, HCT-15, CNS cancer U251, melanoma LOX IMVI, renal cancer A498, prostate cancer PC-3, and breast cancer MDA-MB-468 cell lines (GI50 = 3.91, 3.45, 3.49, 3.21, 1.96, 5.18, 3.69, 1.80, 5.19, and 5.55 μM, respectively). All new compounds were screened for their antimicrobial activity and were very active against P. aeruginosa. Compounds 10a and 16 were twice as active as ampicillin against P. aeruginosa. Five compounds, 9a, b, 10b, 13, and 14 were equipotent to ampicillin against P. aeruginosa. In addition, compound 16 showed a broad spectrum antimicrobial activity. Furthermore, compound 9a showed dual activity as an anticancer and antimicrobial agent. This journal is
Issa, Doaa A. E.,Habib, Nargues S.,Abdel Wahab, Abeer E.
p. 202 - 211
(2015/02/05)

Cation-triggered switchable asymmetric catalysis with chiral aza-crownphos
An aza-crown ether, modified phosphoramidite ligand, has been designed and synthesized. The ON/OFF reversible switch of catalytic activity for its rhodium catalyst was thoroughly investigated in the asymmetric hydrogenation of dehydroamino acid esters modulated by host-guest interactions. In the OFF state, the catalyst is almost inactive (less than 1% conversion) because of the formation of an intermolecular sandwich complex by two aza-crown ether moities and the cationic rhodium metal center. In using alkali-metal-cations as the trigger, the catalytic activity was turned ON and consequently resulted in full conversions and excellent enantioselectivities (up to 98% ee).
Ouyang, Guang-Hui,He, Yan-Mei,Li, Yong,Xiang, Jun-Feng,Fan, Qing-Hua
supporting information
p. 4334 - 4337
(2015/04/14)

Synthesis and biological evaluation of 7H-thiazolo[3,2-b]-1,2,4-triazin-7- one derivatives as dual binding site acetylcholinesterase inhibitors
A series of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives 7a-i were synthesized and evaluated as novel acetylcholinesterase (AChE) inhibitors. All target compounds were evaluated in vitro for the inhibitory activities against AChE via Ellman colorimetric assay. Compound 7c showed an excellent (89.82%) inhibitory activity. The molecular docking studies revealed that 7c, 7d and 7g, with the lateral chain in the para position of the phenyl ring, possessed an optimal docking pose and can perfectly fit into the catalytic active site (CAS) and peripheral anionic site (PAS), simultaneously, and, consequently, exhibited higher inhibitory potency than 7b that bears the same lateral chain as 7g, but in the ortho position of the phenyl ring.
Liu, Sijie,Shang, Ruofeng,Shi, Lanxiang,Wan, David Chi-Cheong,Lin, Huangquan
p. 237 - 244
(2014/06/09)

N-Acetyl-5-arylidenetetramic acids: Synthesis, X-ray structure elucidation and application to the preparation of zinc(II) and copper(II) complexes
A new route to N-acetyl-3-acyl-5-arylidenetetramic acids was developed and applied to the synthesis of a small library of compounds with diversity at carbon 3 of the heterocyclic ring. The 3-acetyl derivative was used as ligand for complexation with zinc(II) and copper(II) acetates. Both the ligand and the zinc complex were studied by X-ray single crystal structure analysis, the zinc complex forms ribbons by H-bonding from the ethanol to a neighbouring molecule.
Matiadis, Dimitris,Igglessi-Markopoulou, Olga,McKee, Vickie,Markopoulos, John
supporting information
p. 2439 - 2443
(2014/04/03)

A concise approach to polysubstituted oxazoles from N-acyl-2-bromo enamides via a copper(i)/amino acid-catalyzed intramolecular C-O bond formation
A straightforward and efficient copper(i)/amino acid-catalyzed intramolecular Ullmann-type C-O coupling reaction has been developed. This protocol affords a facile methodology for the synthesis of a series of novel 2,4,5-substituted oxazoles from readily accessible N-acyl-2-bromo enamides under mild conditions. This journal is the Partner Organisations 2014.
Liu, Bingjie,Zhang, Yueteng,Huang, Gang,Zhang, Xinting,Niu, Pengfei,Wu, Jie,Yu, Wenquan,Chang, Junbiao
p. 3912 - 3923
(2014/06/09)

Synthesis, in-vitroreverse transcriptase inhibitory activity and docking study of some new imidazol-5-one analogs
Non-nucleoside reverse transcriptase inhibitors have a definitive role and most commonly used in treatment of HIV-1 infection. A new series of 4-ethylidene/substituted-benzylidene-1-(4-hydroxy/chloro-6-methylpyrimidin-2-yl) -2-ethyl/phenyl-1H-imidazol-5(4H)-one were designed, synthesized, and evaluated for HIV-1 reverse transcriptase (RT) inhibitory activity. The results of in-vitro HIV-1 RT assay showed that some of the new compounds, such as 4c, 4d, 4e, 5a, and 5e effectively inhibit HIV-1 RT activity. 1-(4-Chloro-6- methylpyrimidin-2-yl)-4-(furan-2-ylmethylene)-2-methyl-1H-imidazol-5(4H)-one (5e) exerted most potent in-vitro HIV-1 RT inhibitory activity, among the group of compounds. Molecular docking studies were carried out to explore the binding affinity of imidazole-5-one analogs in active site of HIV-1 RT enzyme. Springer Science+Business Media 2014.
Mokale, Santosh N.,Lokwani, Deepak K.,Shinde, Devanand B.
p. 3752 - 3764
(2014/08/05)

Asymmetric synthesis of unnatural amino acids and tamsulosin chiral intermediate
An efficient and enantioselective hydrogenation of N-acetylamino phenyl acrylic acids was successfully developed by using ruthenium catalyst. This methodology is important in the field of pharmaceuticals and provides a new process for the preparation of unnatural amino acids and tamsulosin chiral intermediate.
Arava, Veera Reddy,Amasa, Srinivasulu Reddy,Goud Bhatthula, Bharat Kumar,Kompella, Laxmi Srinivas,Matta, Venkata Prasad,Subha
supporting information
p. 2892 - 2897
(2013/09/02)

Microwave-assisted synthesis and antimicrobial screening of new imidazole derivatives bearing 4-thiazolidinone nucleus
A new series of compounds 2-((1-(4-(4-arylidene-2-methyl-5-oxo-4,5-dihydro- 1H-imidazol-1-yl)phenyl)ethylidene)hydrazono)thiazolidin-4-ones (4a-o) have been synthesized under conventional and microwave irradiation method. All compounds were characterized by IR, 1H NMR, 13C NMR and mass spectra. Newly synthesized compounds were screened for their antibacterial and antifungal activities on Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Staphylococcus pyogenes, Candida albicans, Aspergillus niger and Aspergillus clavatus by bioassays, namely serial broth dilution. The synthesized compounds showed potent antimicrobial activity against tested microorganisms. Compounds 4h, 4j, 4m and 4n were the most potent amongst tested compounds.
Desai,Joshi,Rajpara,Vaghani,Satodiya
p. 1893 - 1908
(2013/07/26)

Synthesis and antibacterial activity of some new hydrazones
New hydrazone derivatives were synthesized by the condensation of some selected heteroaromatic hydrazines with appropriate aromatic ketones at high temperature (100 °C). The structures of the synthesized compounds were established by elemental (CHN) and spectral (IR, 1HNMR, and Mass) analysis. The synthesized compounds were screened for their antibacterial (Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi, Proteus mirabilis) activities, which reveal that all the compounds possess activity against all the tested organisms.
Rudrapal,Satyanandam, R. Siva,Swaroopini, T. Sri,Lakshmi, T. Naga,Jaha, S. Kamar,Zaheera
p. 2840 - 2846
(2013/07/26)

Design, synthesis, and biological evaluation of 7H-thiazolo[3,2-b]-1,2,4- triazin-7-one derivatives as dual binding site acetylcholinesterase inhibitors
A series of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives were designed, synthesized and evaluated as dual binding site acetylcholinesterase inhibitors. The target compounds exhibited promising inhibitory activity for AChE. The structure-activity relationships were discussed and their binding conformation and simultaneous interactions mode were further clarified by the molecular docking studies.
Liu, Si-Jie,Cui, Li-Bo,Xu, Hui-Lan,Wang, Tie-Ying,Hu, Chun,Li, Shuo,Lin, Huang-Quan,Wan, David Chicheong
p. 2607 - 2614
(2014/01/06)

Synthesis, biological activity and docking study of imidazol-5-one as novel non-nucleoside HIV-1 reverse transcriptase inhibitors
A novel series of substituted imidazol-5-ones were designed, synthesized and evaluated for in vitro reverse transcriptase (RT) inhibition activity using reverse transcriptase assay kit (Roche, Colorimetric). It has been observed from in vitro screening that newly synthesized compounds possess RT inhibitory activity. Docking study was performed to study the binding orientation and affinity of synthesized compounds for RT enzyme.
Mokale, Santosh N.,Lokwani, Deepak,Shinde, Devanand B.
experimental part
p. 3119 - 3127
(2012/06/29)

Facile synthesis of 4-arylidene-5-imidazolinones as synthetic analogs of fluorescent protein chromophore
A facile and effective synthesis for a wide variety of 4-arylidene-5- imidazolinone derivatives was developed. 4-Arylidene-5-oxazolinones were prepared by Erlenmeyer azlactone synthesis from N-acylglycines and arylaldehydes. The ring-opening reactions of the 4-arylidene-5-oxazolinones with primary amines afforded 2-acylamino-3-arylacrylamides in excellent yields. A new dehydrative cyclization of the 2-acylamino-3-arylacrylamides in pyridine under reflux furnished the corresponding 4-arylidene-5-imidazolinones in good yields.
Lee, Cheng-Yu,Chen, Yun-Chung,Lin, Hao-Chun,Jhong, Yuandong,Chang, Chih-Wei,Tsai, Ching-Hua,Kao, Chai-Lin,Chien, Tun-Cheng
supporting information; experimental part
p. 5898 - 5907
(2012/09/07)

Synthesis and anti-inflammatory activity of imidazo[1,2-a] pyridinyl/pyrazinyl benzamides and acetamides
The present study involves synthesis and determination of anti-inflammatory activity of a series of imidazo[1,2-a]pyridinyl/pyrazinyl benzamides and acetamides. Sixteen new imidazo[1,2-a]pyridinyl/pyrazinyl benzamides and acetamides have been prepared by the ring opening of 4-arylidene-2-methyl/ phenyloxazolones with 2-amino azaheterocycles. All the compounds show significant anti-inflammatory activity. The anti-inflammatory activity studies reveal that both acetamide and benzamide derivatives are equally active. Among the two classes of compounds, i.e., imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrazines, the latter show better activity.
Hemasrilatha,Sruthi,Manjula,Harinadha Babu,Vittal Rao
scheme or table
p. 981 - 987
(2012/09/22)

Synthesis and antiviral activity of new acrylamide derivatives containing 1,2,3-thiadiazole as inhibitors of hepatitis B virus replication
A series of new acrylamide derivatives containing 1,2,3-thiadiazole were synthesized, characterized, and evaluated for their anti-hepatitis B virus (HBV) activities in vitro. The IC50 of compounds 9b (10.4?μg/mL), 9c (3.59?μg/mL) and 17a (9.00?μg/mL) of the inhibition on the replication of HBV DNA were higher than that of the positive control lamivudine (14.8?μg/mL). Compound 9d exhibited significant activity against secretion of HBeAg (IC50?=?12.26?μg/mL).
Dong, Wei-Li,Liu, Zheng-Xiao,Liu, Xing-Hai,Li, Zheng-Ming,Zhao, Wei-Guang
scheme or table
p. 1919 - 1926
(2010/06/19)

Synthesis of 5H-dibenzo (b,f) azepine-5-{4-substitutedbenzylidene-2- methylimidazole-5-one}-carboxamides and their antioxidant activity
A series of 5H-dibenzo (b,f) azepine-5-{4-substitutedbenzylidene-2- methylimidazole5-one}-carboxamides were synthesized and characterized on the basis of IR, 1H NMR, .and mass spectral (MS) data. The title compounds were subjected to in-vitro antioxidant testing using DPPH method. Some of the compounds showed significant antioxidant activity when compared with standard ascorbic acid.
Kaur, Ranjit,Rao, Gopal Krishna,Pai, P. N. Sanjay
body text
p. 261 - 264
(2011/12/05)

A novel three-component synthesis of triazinothiazolones
A series of 4-arylidene-2-methyloxazol-5-ones 1 were condensed with thiosemi-carbazide to yield 6-arylmethyl-3-mercapto-1,2,4-triazin-5-ones 2. The resulting mercapto triazinones 2 were condensed with monochloroacetic acid and 5-aryl-furan-2-carboxaldehydes 3 in a one-pot three-component reaction in the presence of acetic anhydride, acetic acid, and sodium acetate to yield 4-substituted-5-oxo-7-(5-aryl-2-furfurylidene)-1,2,4-triazino[3,4-b] -thiazol-6-ones 4. Some of the newly synthesized compounds were tested for their antibacterial activity against Gram (+)ve and Gram (-)ve bacteria. The results of such studies are discussed in this paper. Copyright Taylor & Francis, Inc.
Holla, Bantval Shivarama,Malini, Kani Veetil,Sarojini, Balladka Kunhanna,Poojary, Boja
p. 333 - 340
(2007/10/03)

Solid support Erlenmeyer synthesis of azlactones using microwaves
A rapid and efficient protocol for the synthesis of azlactones is reported starting from acetyl/benzoylglycine and various aromatic aldehydes in the presence of acetic anhydride and sodium acetate in dry media using silica gel as solid support under microwave irradiation. The mild conditions, excellent yields, high purity. short reaction time and easy work-up are some of the major advantages of this method.
Mogilaiah,Prashanthi,Reddy, Ch. Srinivas
p. 2126 - 2128
(2007/10/03)

An improved "one-pot" procedure for synthesis of fluorinated DL-phenylalanines
DL-arylalanines were synthesized from corresponding aromatic aldehydes by an efficient "one-pot" procedure involving Erlenmeyer reaction and subsequent reduction of the resulting oxazolones (without prior isolation) using P/HI.
Samet, Alexander V.,Coughlin, Daniel J.,Buchanan III,Gakh, Andrei A.
p. 941 - 946
(2007/10/03)

Mechanism of ring opening reaction of 4-benzylidene-2-methyl-5-oxazolone. Part I. Reaction with n-butylamine
The reaction between 4-benzylidene-2-methyl-5-oxazolone (Ox, c = 5.25 × 10-5 M) with n-butylamine (nBuA, c = 0.026 to 1.66 M) in acetonitrile was studied by UV-Vis spectroscopy using steady-state and stopped-flow apparatus. The amine to Ox molar ratio higher than 500 allows to apply pseudo-first order approximation, whose rate constants depend on amine concentration according to a parabolic equation: kobs = 4.63 ± 0.02 × C2nBuA, indicating a complex reaction mechanism. On the other hand, singular value decomposition (SVD) analysis, as well as global analysis of the data obtained from stopped-flow measurements support a simple A → B reaction model. Nonlinear dependence of the pseudo-first order rate constant on amine concentration can be explained, assuming that the oxazolone ring opening reaction by n-butylamine in acetonitrile proceeds as parallel reactions: A + B → C and A+2B → C. Based on our experimental results and theoretical calculations of the oxazolone ring opening reaction, a mechanism of the reaction between 4-benzylidene-2-methyl-5-oxazolone and n-butylamine is proposed.
Betlakowska,Banecki,Lankiewiez,Wiczk
p. 401 - 410
(2007/10/03)

Complexes of Ca2+ and Mg2+ with N-acetyl-α,β-dehydrodipeptides: The state in an alcoholic solution and its relationship with asymmetric induction upon diastereoselective hydrogenation
In an alcoholic solution, N-acetyl-α,β-dehydrodipeptides interact with Ca2+ and Mg2+ ions to form complex particles containing several dehydrodipeptide molecules per metal ion. The composition of these particles and steric interactions in them determine the acidity of the carboxyl groups and the degree of asymmetric induction upon diastereoselective hydrogenation.
Lisichkina,Larina,Peregudov,Vasil'era,Belikov
p. 895 - 898
(2007/10/03)

Studies on arylmethyltriazinone derivatives-Part II. Synthesis and antifungal properties of 2-aminomethyl-4-(arylidene)amino-6-arylmethyl-3-mercapto-1, 2,4-triazin-5(4H)-ones
The preparation of twenty new 2-aminomethyl-4-(arylidene)amino-6-arylmethyl-3-mercapto-1,2,4-triazin-5(4H)- ones(4) is described. The structural elucidation of all the compounds is carried out on the basis of analytical and spectral data. The newly synthesized compounds are evaluated for their antifungal activity against Candida albicans and Paecileomyces variotti.
Holla,Gonsalves,Shivananda
p. 93 - 96
(2007/10/03)

Chemocontrolled reduction of aromatic α-ketoesters by NaBH4: Selective synthesis of α-hydroxy esters or 1,2-diols
α-Hydroxyesters 5a-g or diols 6a-g have been obtained in high yields by reduction of aromatic α-ketoesters 4 once or twice respectively by using NaBH4 as the reducer under suitable conditions. The use of a solvent that does not interact with the reagent allowed the double reduction to occur with only a slight excess of borohydride in very mild conditions.
Dalla, Vincent,Cotelle, Philippe,Catteau, Jean Pierre
p. 1577 - 1580
(2007/10/03)

Synthesis of substituted quinazolone derivatives as potential anti-HIV agents (part III)
Several 1-[2-phenyl-4(4H)-oxo-3-quinazolinyl]-2-methyl-4-arylidine -5-oxo-imidazolines (Va-1), 2-phenyl-3-(aroyl amino)-4(4H)-oxo quinazolines (Vla-I) and N1-2-methyl-4(4H)-oxo-3-quinazolinyl-N2-aryl-thioureas (Vlla-k), have been synthesised and tested for anti-HIV activity. The structures of these compounds have been established on the basis of elemental analysis and spectral data.
Desai,Bhatt,Shah,Undavia,Trivedi,Narayanan
p. 361 - 366
(2007/10/03)

Novel Imidazole Congeners as Anti-inflammatory Agents
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Bhalla, Manish,Naithani, P. K.,Bhalla, T. N.,Saxena, A. K.,Shanker, K.
p. 594 - 595
(2007/10/02)

Synthesis and antiparkinsonian activity of newer imidazolones
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Naithani,Srivastava,Barthwal,Saxena,Gupta,Shanker
p. 990 - 992
(2007/10/02)

Metal Ion Effects in Intramolecular Reactions. Effects of Divalent Metal Ions on Intramolecular Acetamido Group Participation in Ester Hydrolysis
The hydrolysis reactions of a series of esters of α-acetamidocinnamic acid proceed with formation of an oxazolinone intermediate.In 50percent dioxane-H2O (v/v) at 50 deg C, an oxazolinone can be observed spectrophotometrically in the OH- catalyzed cyclization reactions of the α-acetamido-substituted esters with leaving groups of pKa 12.4 or less.In comparison with the OH- catalyzed hydrolysis of the corresponding cinnamate esters, the rate enhancement due to the presence of the acetamido group is a factor of 200 with the trifluoroethyl ester and increases to 2x1E6 with the p-nitrophenyl ester.The plot of log kOH vs ?, the Hammett substituent constant, is linear and has a slope (ρ) of 2.7 (1.8 when ?- is employed) for the cyclization reactions of the phenolic esters, but the ρ value is only 1.4 for the OH- catalyzed hydrolysis of the corresponding cinnamates.The slope of log kOH vs the pKa of the leaving group for the cyclization of the α-acetamidocinnamic acid derivatives, βlg, is -0.9.Thus, there must be considerable C-O bond breaking in the critical transition state for oxazolinone formation.In H2O as the solvent, 6-carboxy-2-pyridylmethyl α-(N-acetylamino)cinnamate and the corresponding 2-pyridylmethyl derivative cyclize rapidly to the oxazolinone with KOH (5xE4)-fold larger than that for hydrolysis of 2-pyridylmethyl cinnamate, even though the leaving group is an aliphatic alcohol.There is significant metal ion catalysis in the cyclization reactions with Cu2+, Ni2+, Co2+ or Zn2+.The binding of the metal ions to the 6-carboxy-substituted derivative is very strong, and saturation occurs at metal ion concentrations less than 0.01 M.A saturating concentration of Cu2+ (0.001 M) enhances the rate of cyclization by a factor of 5x1E4.Thus, the total rate enhancement provided by bifunctional catalysis (Cu2+ and the neighboring acetamido group) is 1E9-fold.Metal ion binding to 2-pyridylmethyl α-(N-acetylamino)cinnamate is weak, but nevertheless, the second-order rate constants kOH are similar to those of the 6-carboxy-substituted ester at equal metal ion concentrations.The metal ions must exert their catalytic effect by stabilizing the leaving group alcohol in the transition state.This appears to be a general mechanism for metal ion catalysis of reactions in which C-O bond breaking is the rate-determining step.
Fife, Thomas H.,Przystas, Theodore J.,Pujari, Mahesh P.
p. 8157 - 8163
(2007/10/02)

Synthesis and antimicrobial evaluation of 1-(phenyl/methylcarbamoyloxyphenyl)-2-methyl/phenyl-4-(substituted benzylidene)-5-imidazolone, a new class of carbamates
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Sengupta,Gupta
p. 724 - 726
(2007/10/02)

Tumor-resolving and histolytic medicaments and their use
Dehydrooligopeptides, some of which are known, demonstrate histolytic and tumor-resolving activity and may be used in medicaments causing the lysis of animal tissues and/or tumors in warm-blooded animals.
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(2008/06/13)

Synthesis of Some New I-(Substituted Sulphamidophenyl)-2-Methyl/Aryl-4-(Substituted Benzylidene)-5-Imidazolones
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Gupta, Anil K. Sen,Gupta, Anurag Ateet
p. 297 - 299
(2007/10/02)