- Study on the synthesis of sulfonamide derivatives and their interaction with bovine serum albumin
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Three sulfonamide derivatives (SAD) were first synthesized from p-hydroxybenzoic acid and sulfonamides (sulfadimidine, sulfamethoxazole and sulfachloropyridazine sodium) and were characterized by elemental analysis, 1H NMR and MS. The interaction between bovine serum albumin (BSA) and SAD was studied using UV/vis absorption spectroscopy, fluorescence spectroscopy, time-resolved fluorescence spectroscopy and circular dichroism spectra under imitated physiological conditions. The experimental results indicated that SAD effectively quenched the intrinsic fluorescence of BSA via a static quenching process. The thermodynamic parameters showed that hydrogen bonding and van der Waal's forces were the predominant intermolecular forces between BSA and two SADs [4-((4-(N-(4,6-dimethylpyrimidin-2-yl)sulfamoyl)phenyl)carbamoyl)phenyl acetate and 4-((4-(N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)carbamoyl)phenyl acetate], but hydrophobic forces played a major role in the binding process of BSA and 4-((4-(N-(6-chloropyridazin-3-yl)sulfamoyl)phenyl) carbamoyl)phenyl acetate. In addition, the effect of SAD on the conformation of BSA was investigated using synchronous fluorescence spectroscopy and circular dichroism spectra. Molecular modeling results showed that SAD was situated in subdomain IIA of BSA.
- Zhang, Xuehong,Lin, Yijie,Liu, Lina,Lin, Cuiwu
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Read Online
- Discovery of β-Adrenergic Receptors Blocker-Carbonic Anhydrase Inhibitor Hybrids for Multitargeted Antiglaucoma Therapy
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The combination of a β-adrenergic receptors (AR) blocker and a carbonic anhydrase (CA, EC 4.2.1.1) inhibitor in eye drops formulations is one of the most clinically used treatment for glaucoma. A novel approach consisting of single-molecule, multitargeted compounds for the treatment of glaucoma is proposed here by designing compounds which concomitantly interact with the β-adrenergic and CA targets. Most derivatives of the two series of benzenesulfonamides incorporating 2-hydroxypropylamine moieties reported here exhibited striking efficacy against the target hCA II and XII, whereas a subset of compounds also showed significant modulation of β1- and β2-ARs. X-ray crystallography studies provided rationale for the observed hCA inhibition. The best dual-agents decreased IOP more effectively than clinically used dorzolamide, timolol, and the combination of them in an animal model of glaucoma. The reported evidence supports the proof-of-concept of β-ARs blocker-CAI hybrids for antiglaucoma therapy with an innovative mechanism of action.
- Nocentini, Alessio,Ceruso, Mariangela,Bua, Silvia,Lomelino, Carrie L.,Andring, Jacob T.,McKenna, Robert,Lanzi, Cecilia,Sgambellone, Silvia,Pecori, Riccardo,Matucci, Rosanna,Filippi, Luca,Gratteri, Paola,Carta, Fabrizio,Masini, Emanuela,Selleri, Silvia,Supuran, Claudiu T.
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Read Online
- Identification of Novel Resorcinol Amide Derivatives as Potent and Specific Pyruvate Dehydrogenase Kinase (PDHK) Inhibitors
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Pyruvate dehydrogenase kinases (PDHKs) promote abnormal respiration in cancer cells. Studies with novel resorcinol amide derivatives based on VER-246608 (6) led to the identification of 19n and 19t containing five-membered heteroaromatic rings as unique structural features. These substances possess single-digit nanomolar activities against PDHKs. 19t exhibits higher potencies against PDHK1/2/4 than does 6 and inhibits only PDHKs among 366 kinases. Moreover, 19g, 19l, and 19s were found to be isotype-selective PDHK inhibitors. Molecular dynamics simulations provide a better understanding of how the heteroaromatic rings affect the activities of 19n and 19t on PDHK1/2/3/4. Moreover, 19n possesses a much higher antiproliferative activity against cancer cells than does 6. We demonstrated that the results of PDH assays better correlate with cellular activities than do those of PDHK kinase assays. Furthermore, 19n induces apoptosis of cancer cells via mitochondrial dysfunction, suppresses tumorigenesis, and displays a synergistic effect on satraplatin suppression of cancer cell proliferation.
- Cho, Hanna,Cho, Kyungseon,Kim, Mi-Jin,Kim, Nam Doo,Lee, In-Kyu,Park, Sungmi,Shin, Injae,Sim, Taebo,Yoo, Eun Kyung,Yoon, Hojong
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Read Online
- Photo-induced deep aerobic oxidation of alkyl aromatics
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Oxidation is a major chemical process to produce oxygenated chemicals in both nature and the chemical industry. Presently, the industrial manufacture of benzoic acids and benzene polycarboxylic acids (BPCAs) is mainly based on the deep oxidation of polyalkyl benzene, which is somewhat suffering from environmental and economical disadvantage due to the formation of ozone-depleting MeBr and corrosion hazards of production equipment. In this report, photo-induced deep aerobic oxidation of (poly)alkyl benzene to benzene (poly)carboxylic acids was developed. CeCl3 was proved to be an efficient HAT (hydrogen atom transfer) catalyst in the presence of alcohol as both hydrogen and electron shuttle. Dioxygen (O2) was found as a sole terminal oxidant. In most cases, pure products were easily isolated by simple filtration, implying large-scale implementation advantages. The reaction provides an ideal protocol to produce valuable fine chemicals from naturally abundant petroleum feedstocks. [Figure not available: see fulltext.].
- Wang, Chang-Cheng,Zhang, Guo-Xiang,Zuo, Zhi-Wei,Zeng, Rong,Zhai, Dan-Dan,Liu, Feng,Shi, Zhang-Jie
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p. 1487 - 1492
(2021/07/10)
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- Aryl alkyl ether compound as well as derivative, preparation method, pharmaceutical composition and application thereof
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The invention discloses an aryl alkyl ether compound as well as a derivative, a preparation method, a pharmaceutical composition and application thereof. The structure of the aryl alkyl ether compound is shown as a formula (I). The aryl alkyl ether compound derivative relates to a stereoisomer, a tautomer, a metabolite, a metabolic precursor, a prodrug, a solvate, a salt of the solvate, a crystal, a pharmaceutically acceptable salt or a mixture of the stereoisomer, the tautomer, the metabolite, the metabolic precursor, the prodrug and the solvate of the aryl alkyl ether compound. The aryl alkyl ether compound and the derivative thereof have a remarkable inhibition effect on indoleamine 2, 3-dioxygenase 1, and can be used for preparing a medicine for treating indoleamine 2, 3-dioxygenase 1 mediated immunosuppression related diseases, and the prepared medicine can exert the medicine effect at the molecular level and is wide in application.
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Paragraph 0261; 0262; 0265; 0266
(2021/05/12)
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- Structure-Activity Study of Nitazoxanide Derivatives as Novel STAT3 Pathway Inhibitors
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We identified nitazoxanide (NTZ) as a moderate STAT3 pathway inhibitor through immunoblot analysis and a cell-based IL-6/JAK/STAT3 pathway activation assay. A series of thiazolide derivatives were designed and synthesized to further validate the thiazolide scaffold as STAT3 inhibitors. Eight out of 25 derivatives displayed potencies greater than that of NTZ, and their STAT3 pathway inhibitory activities were found to be significantly correlated with their antiproliferative activities in HeLa cells. Derivatives 15 and 24 were observed to be more potent than the positive control WP1066, which is under phase I clinical trials. Compared with NTZ, 15 also exhibited much improved in vivo pharmacokinetic parameters in rats and efficacies against proliferations in multiple cancer cell lines, indicating a broad-spectrum effect of these thiazolides as antitumor agents targeted on STAT3.
- Lü, Zirui,Li, Xiaona,Li, Kebin,Wang, Cong,Du, Tingting,Huang, Wei,Ji, Ming,Li, Changhong,Xu, Fengrong,Xu, Ping,Niu, Yan
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supporting information
p. 696 - 703
(2021/05/04)
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- PROCESSES FOR PREPARING AN S1P-RECEPTOR MODULATOR
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This application relates to processes for preparing an S1P-receptor modulator "Compound 1", which is useful in the treatment of diseases or disorders associated with activity of S1P, including CNS disorders. The process comprises reacting "compound 2" with "compound 3" in the presence of a reducing agent.
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Page/Page column 33
(2021/05/07)
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- Synthesis and antioxidant activities of berberine 9-: O -benzoic acid derivatives
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Although berberine (BBR) shows antioxidant activity, its activity is limited. We synthesized 9-O-benzoic acid berberine derivatives, and their antioxidant activities were screened via ABTS, DPPH, HOSC and FRAP assays. The para-position was modified with halogen elements on the benzoic acid ring, which led to an enhanced antioxidant activity and the substituent on the ortho-position was found to be better than the meta-position. Compounds 8p, 8c, 8d, 8i, 8j, 8l, and especially 8p showed significantly higher antioxidant activities, which could be attributed to the electronic donating groups. All the berberine derivatives possessed proper lipophilicities. In conclusion, compound 8p is a promising antioxidant candidate with remarkable elevated antioxidant activity and moderate lipophilicity.
- Liu, Yanfei,Long, Shuo,Zhang, Shanshan,Tan, Yifu,Wang, Ting,Wu, Yuwei,Jiang, Ting,Liu, Xiaoqin,Peng, Dongming,Liu, Zhenbao
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p. 17611 - 17621
(2021/05/29)
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- Cleavage of Carboxylic Esters by Aluminum and Iodine
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A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.
- Sang, Dayong,Yue, Huaxin,Fu, Yang,Tian, Juan
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p. 4254 - 4261
(2021/03/09)
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- Heterogeneous vanadium-catalyzed oxidative cleavage of olefins for sustainable synthesis of carboxylic acids
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The development of green and sustainable processes to synthesize active pharmaceutical ingredients and key starting materials is a priority for the pharmaceutical industry. A green and sustainable protocol for the oxidative cleavage of olefins to produce pharmaceutically and biologically valuable carboxylic acids is achieved. The developed protocol involves 70% aq. TBHP as an oxidant over a heterogeneous vanadium catalyst system. Notably, the synthesis of industrially important azelaic acid from various renewable vegetable oils is accomplished. The catalyst could be recycled for up to 5 cycles without significant loss in yield and the protocol was successfully demonstrated at the gram-scale.
- Upadhyay, Rahul,Rana, Rohit,Sood, Aakriti,Singh, Vikash,Kumar, Rahul,Srivastava, Vimal Chandra,Maurya, Sushil K.
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supporting information
p. 5430 - 5433
(2021/06/09)
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- 1,2-Dibutoxyethane-Promoted Oxidative Cleavage of Olefins into Carboxylic Acids Using O2 under Clean Conditions
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Herein, we report the first example of an effective and green approach for the oxidative cleavage of olefins to carboxylic acids using a 1,2-dibutoxyethane/O2 system under clean conditions. This novel oxidation system also has excellent functional-group tolerance and is applicable for large-scale synthesis. The target products were prepared in good to excellent yields by a one-pot sequential transformation without an external initiator, catalyst, and additive.
- Ou, Jinhua,Tan, Hong,He, Saiyu,Wang, Wei,Hu, Bonian,Yu, Gang,Liu, Kaijian
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p. 14974 - 14982
(2021/10/25)
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- Production device of liquid crystal polymer precursor acetylated monomer
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The utility model provides a production device of a liquid crystal polymer precursor acetylated monomer, which comprises a raw material dissolving tank, a micro-mixer, a micro-channel reactor and a receiving system which are sequentially communicated through pipelines along the material flow direction. By adopting the microchannel reactor, the heat exchange capability of the reactor in the reaction process is enhanced, the defect of large temperature fluctuation of the phenolic hydroxyl-containing aromatic compound in the acetylation reaction process by adopting the traditional method is overcome, the high selectivity of the reaction is realized by accurately controlling the temperature, the generation of by-products is reduced, and the production cost is reduced. The purity of the monomeris improved, a high-purity polymerized monomer is provided for the subsequent melt polycondensation reaction, and the performance of the liquid crystal polymer prepared by the polycondensation reaction is greatly improved.
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Paragraph 0090-0095
(2021/03/24)
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- Synthesis, biological evaluation and molecular modeling study of 2-amino-3,5-disubstituted-pyrazines as Aurora kinases inhibitors
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Serine/threonine protein kinases Aurora A, B, and C play essential roles in cell mitosis and cytokinesis, and a number of Aurora kinase inhibitors have been evaluated in the clinic. Herein we report the synthesis and their antiproliferation of 3,5-disubstituted-2-aminopyrazines as kinases inhibitors. Amongst, 4-((3-amino-6- (3,5-dimethylisoxazol-4-yl)pyrazin-2-yl)oxy)-N-(3-chlorophenyl) benzamide (12Aj) exhibited the strongest antiproliferative activities against U38, HeLa, HepG2 and LoVo cells with IC50 values were 11.5 ± 3.2, 1.34 ± 0.23, 7.30 ± 1.56 and 1.64 ± 0.48 μM, as well as inhibited Aurora A and B with the IC50 values were 90 and 152 nM, respectively. Molecular docking studies indicated that 12Aj appeared to form stable hydrogen bonds with either Aurora A or Aurora B. Furthermore, 12Aj arrested HeLa cell cycle in G2/M phase by regulating protein levels of cyclinB1 and cdc2. In addition, the bioinformatics prediction further revealed that 12Aj possessed good drug likeness using SwissADME. These results suggested that 12Aj was worthy of future development of potent anticancer agents as pan-Aurora kinases.
- Bo, Yong-Xin,Chen, Shi-Wu,Hao, Shu-Yi,Wang, Xing-Rong,Xiang, Rong,Xu, Yu
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- Structure-activity relationship study and biological evaluation of SAC-Garlic acid conjugates as novel anti-inflammatory agents
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A series of S-allyl-L-cysteine (SAC) with garlic acid conjugates as anti-inflammatory agents were designed and synthesized. Among the 40 tested compounds, SMU-8c exhibited the most potent inhibitory activity to Pam3CSK4-induced nitric oxide (NO) in RAW264.7 macrophages with IC50 of 22.54 ± 2.60 μM. The structure-activity relationship (SAR) study suggested that the esterified carboxyl group, carbon chain extension and methoxylation phenol hydroxy could improve the anti-inflammatory efficacy. Preliminary anti-inflammatory mechanism studies showed that SMU-8c significantly down-regulated the levels of Pam3CSK4 triggered TNF-α cytokine in human THP-1 cells, mouse RAW 264.7 macrophages, as well as in ex-vivo human peripheral blood mononuclear cells (PBMC) with no influence on cell viability. SMU-8c specifically blocked the Pam3CSK4 ignited secreted embryonic alkaline phosphatase (SEAP) signaling with no influence to Poly I:C or LPS triggered TLR3 or TLR4 signaling. Moreover, SMU-8c suppressed TLR2 in HEK-Blue hTLR2 cells and inhibited the formation of TLR1-TLR2, and TLR2-TLR6 complex in human PBMC. In summary, SMU-8c inhibited the TLR2 signaling pathway to down-regulate the inflammation cytokines, such as NO, SEAP and TNF-α, to realize its anti-inflammatory activity.
- Bi, Jingjie,Wang, Wenqing,Du, Junxi,Chen, Kun,Cheng, Kui
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p. 233 - 245
(2019/07/02)
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- Histone deacetylases inhibitor and use thereof
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The present invention relates to a novel histone deacetylase (HDAC) inhibitor and a medical use thereof. More specifically, it is confirmed that a novel aspirin derivative inhibits the activity of HDAC by bonding to a substrate bonding pocket of HDAC and significantly increases the acetylation of intracellular andalpha;-tubulin and histone H3, thereby exhibiting an effect of inhibiting cancer cell proliferation. The novel aspirin derivative is provided as HDAC inhibitors, thereby being able to be provided as a therapeutic agent effective for HDAC-related cancer diseases and central nervous system diseases.COPYRIGHT KIPO 2020
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Paragraph 0071-0073; 0136; 0137
(2019/12/25)
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- Reversible Spatial Control in Aqueous Media by Visible Light: A Thioindigo Photoswitch that is Soluble and Operates Efficiently in Water
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Aiming to extend the scope of indigoid photoswitches to polar protic environments, we have synthesized a sulfonated thioindigo derivative highly soluble in water. Studies by UV/Vis absorption, fluorescence, and NMR spectroscopy indicate that, despite aggregation effects at micromolar concentrations, the novel dye offers satisfactory performance in aqueous solution in the absence of solvation aides. Enrichment of the metastable cis isomer by irradiation may exceed 65 % and its half-life at room temperature may exceed several hours. Degradation after 20 yellow and blue light irradiation cycles within 2 hours is less than 2 %. Performance can be expected to further improve in future molecular designs if the tendency towards self-association is further reduced. Crucially, photoisomerization of indigoids is not necessarily inhibited by water and, thus, the superior spatial control offered by this class of molecular switches may be of great benefit also in biological systems.
- Koeppe, Benjamin,R?mpp, Florian
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supporting information
p. 14382 - 14386
(2018/09/21)
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- Aspirin-inspired acetyl-donating HDACs inhibitors
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Aspirin is one of the oldest drugs for the treatment of inflammation, fever, and pain. It is reported to covalently modify COX-2 enzyme by acetylating a serine amino acid residue. By virtue of aspirin’s acetylating potential, we for the first time developed novel acetyl-donating HDAC inhibitors. In this study, we report the design, synthesis, in silico docking study, and biological evaluation of acetyl-donating HDAC inhibitors. The exposure of MDA-MB-231 cells with compound 4c significantly promotes the acetylation of α-tubulin and histone H3, which are substrates of HDAC6 and HDAC1, respectively. In silico docking simulation also indicates that compound 4c tightly binds to the deep substrate-binding pocket of HDAC6 by coordinating the active zinc ion in a bidentate manner and forming hydrogen bond interactions with Ser531 and His573 amino acid residues. In particular, compound 4c (GI50 = 147?μM) affords the significant enhancement of anti-proliferative effect on MDA-MB-231 cells, compared with its parent compound 2c (GI50 > 1000?μM) and acetyl-donating group deficient compound 6 (GI50 = 554?μM). Overall, compound 4c presents a novel strategy for developing acetyl-donating HDAC inhibitors.
- Lim, Jiah,Song, Yoojin,Jang, Jung-Hee,Jeong, Chul-Ho,Lee, Sooyeun,Park, Byoungduck,Seo, Young Ho
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p. 967 - 976
(2018/06/25)
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- A mild method for synthesizing carboxylic acids by oxidation of aldoximes using hypervalent iodine reagents
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A mild oxidation method for the conversion of aldoximes to carboxylic acids was developed mediated by hypervalent iodine reagents. This method covers a wide range of functionalized aldoximes and proceeds under mild conditions, utilizing PhI(OH)OTs as an oxidant.
- Nakamura, Akira,Kanou, Hodaka,Tanaka, Junki,Imamiya, Akira,Maegawa, Tomohiro,Miki, Yasuyoshi
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supporting information
p. 541 - 544
(2018/02/07)
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- Thermotropic liquid crystalline polyesters derived from 2-chloro hydroquinone
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Abstract: Synthesis of thermotropic liquid crystalline polyesters derived from bis[4-hydroxy benzoyloxy]-2-chloro-1,4-benzene (BHBOCB) and aliphatic dicarboxylic acid chlorides by interfacial polycondensation methodology is presented. Synthesised polyesters consist of bis[4-hydroxy benzoyloxy]-2-chloro-1,4-benzene as a mesogen and aliphatic diacid chloride as flexible spacer. The length of oligomethylene units in the polymer was varied from the trimethylene to the dodecamethylene groups. Synthesized polyesters were characterized by differential scanning calorimetry and optical microscopy. The transition temperatures and thermodynamic properties were studied for all these polymers. These polyesters exhibited thermotropic liquid crystalline behavior and showed nematic texture except decamethylene spacer. Decamethylene spacer based polyester showed marble texture of smectic C. Mesophase stability of these polyesters was higher than 123 °C (except first heating cycle of PE-1). Graphical Abstract:: SYNOPSIS The present study deals with the synthesis of thermotropic liquid crystalline polyesters derived from bis[4-hydroxy benzoyloxy]-2-chloro-1,4-benzene (BHBOCB) and aliphatic dicarboxylic acid chlorides by interfacial polycondensation methodology. [Figure not available: see fulltext.].
- Manurkar, Nagesh,More, Sayaji,Mulani, Khudbudin,Ganjave, Nitin,Chavan, Nayaku
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p. 1461 - 1468
(2017/09/27)
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- Secondary sulfonamides as effective lactoperoxidase inhibitors
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Secondary sulfonamides (4a-8h) incorporating acetoxybenzamide, triacetoxybenzamide, hydroxybenzamide, and trihydroxybenzamide and possessing thiazole, pyrimidine, pyridine, isoxazole and thiadiazole groups were synthesized. Lactoperoxidase (LPO, E.C.1.11.1.7), as a natural antibacterial agent, is a peroxidase enzyme secreted from salivary, mammary, and other mucosal glands. In the present study, the in vitro inhibitory effects of some secondary sulfonamide derivatives (4a-8h) were examined against LPO. The obtained results reveal that secondary sulfonamide derivatives (4a-8h) are effective LPO inhibitors. The Ki values of secondary sulfonamide derivatives (4a-8h) were found in the range of 1.096 ± 10-3 to 1203.83 μM against LPO. However, the most effective inhibition was found for N-(sulfathiazole)-3,4,5-triacetoxy.
- K?ksal, Zeynep,Kalin, Ramazan,Camadan, Yasemin,Usanmaz, Hande,Almaz, Züleyha,Gül?in, Ilhami,Gokcen, Taner,G?ren, Ahmet Ceyhan,Ozdemir, Hasan
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- Synthetic method for ultraviolet absorbent namely 4,4'-dihexyloxybenzophenone
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The invention discloses a synthetic method for an ultraviolet absorbent namely 4,4'-dihexyloxybenzophenone. The method comprises the following steps: with p-hydroxybenzoic acid as a starting material, carrying out acetylation to protect hydroxy; carrying out a Fredel-Crafts reaction of p-acetoxybenzoic acid and phenol under the catalysis of zinc chloride and phosphorus oxychloride so as to synthesize an intermediate namely phenyl p-hydroxybenzoate; then carrying out deacetylation to remove the protective group, and carrying out Fries rearrangement so as to prepare an intermediate namely 4,4-dihydroxybenzophenone; and forming a salt with 4,4-dihydroxybenzophenone and potassium carbonate, and carrying out a Williamson reaction of 1-bromohexane and the potassium salt of 4,4-dihydroxybenzophenone through catalysis of tetrabutylammonium bromide so as to synthesize the 4,4'-dihexyloxybenzophenone. The synthetic method provided by the invention has the advantages of mild reaction conditions, normal pressure, medium and low temperature, stable quality control, high raw material conversion rate, effective inhibition of side reactions, fewer three wastes, light pollution, and facilitation of protecting the environment and labor of a producer.
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Paragraph 0018; 0019; 0024; 0029; 0034; 0039
(2017/09/13)
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- A Tandem Ring Opening/Closure Reaction in A BF3-Mediated Rearrangement of Spirooxindoles
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Treatment of the readily accessible spiro-cyclohexadienones from the PhI(OCOCF3)2-mediated spiro-cyclization of N-substituted benzanilides, with BF3?Et2O initiates a tandem ring opening/closure reaction leading to the formation of the biologically interesting 8-hydroxy-phenanthridin-6(5H)-one compounds. This unique rearrangement pattern involves the ‘migration’ of the electron-deficient N-methyl carbamoyl moiety rather than the electron-rich aryl group as observed and reported previously in all other similar transformations. (Figure presented.).
- Guo, Xuliang,Xing, Qingyu,Lei, Kunhua,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
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supporting information
p. 4393 - 4398
(2017/10/23)
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- Oxalic acid as the: In situ carbon monoxide generator in palladium-catalyzed hydroxycarbonylation of arylhalides
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An efficient palladium-catalyzed hydroxycarbonylation reaction of arylhalides using oxalic acid as a CO source has been developed. The reaction features high safety, low catalyst loading, and a broad substrate scope, and provides a safe and tractable approach to access a variety of aromatic carboxylic acid compounds. Mechanistic studies revealed the decomposition pattern of oxalic acid.
- Shao, Changdong,Lu, Ailan,Wang, Xiaoling,Zhou, Bo,Guan, Xiaohong,Zhang, Yanghui
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supporting information
p. 5033 - 5040
(2017/07/10)
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- Highly efficient and recyclable acetylation of phenols and alcohols by nickel zirconium phosphate under solvent-free conditions
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Nickel zirconium phosphate nanoparticles have been used as an efficient catalyst for the acetylation of a wide range of alcohols and phenols with acetic anhydride in good to excellent yields under solvent-free conditions. The steric and electronic properties of the different substrates had a significant influence on the reaction conditions required to achieve the acetylation. The catalyst used in the current study was characterized by inductively coupled plasma optical emission spectroscopy, X-ray diffraction, N2 adsorption-desorption, scanning electron microscopy, and transmission electron microscopy. This nanocatalyst could also be recovered and reused at least six times without any discernible decrease in its catalytic activity.
- Hajipour, Abdol Reza,Karimi, Hirbod,Kohi, Afshin
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- A class of sulfonamides as carbonic anhydrase I and II inhibitors
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Four groups of novel sulfonamide derivatives: (i) acetoxybenzamide, (ii) triacetoxybenzamide, (iii) hydroxybenzamide and (iv) trihydroxybenzamide, all having thiazole, pyrimidine, pyridine, isoxazole and thiadiazole moieties were prepared and their inhibitory effects were studied on two metalloenzymes, i.e. carbonic anhydrase isozymes (hCA I and II), purified from human erythrocyte cells by Sepharose-4B-l-tyrosine-sulfanilamide affinity chromatography. These enzymes are present in almost all living organisms to catalyse the synthesis of bicarbonate ion (HCO3 ?) from carbon dioxide and water. The sulfonamide derivatives were found to be active against hCA I and II in the range of 2.62–136.54 and 5.74–210.58 nM, respectively.
- Gokcen, Taner,Gulcin, Ilhami,Ozturk, Turan,Goren, Ahmet C.
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p. 180 - 188
(2016/12/14)
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- INHIBITORS OF BRUTON'S TYROSINE KINASE
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Disclosed herein are compounds that inhibit Bruton's tyrosine kinase (Btk). Also described are irreversible inhibitors of Btk. In addition, reversible inhibitors of Btk are also described. Also disclosed are pharmaceutical compositions that include the compounds. Methods of using the Btk inhibitors are disclosed, alone or in combination with other therapeutic agents, for the treatment of autoimmune diseases or conditions, heteroimmune diseases or conditions, cancer, including lymphoma, and inflammatory diseases or conditions.
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Paragraph 00658
(2016/01/25)
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- A kind of preparation method of the acetoxy benzoic acid
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The invention discloses a p-acetoxybenzoic acid preparation method. The method using p-hydroxybenzoic acid and acetyl chloride as raw materials concretely comprises the following steps: dissolving p-hydroxybenzoic acid in tetrahydrofuran , adding pyridine and acetyl chloride, and reacting at -5 - 5 DEG C, wherein a molar ratio of acetyl chloride to p-hydroxybenzoic acid is 1.1-1.5, and a molar ratio of pyridine to p-hydroxybenzoic acid is 1.1-1.5. The method has the advantages of almost no corrosion to an apparatus, high yield, simple purification and convenient operation.
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Paragraph 0026; 0027
(2017/01/09)
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- POLYORGANOSILOXANE COMPOUND, METHOD FOR PREPARING THE SAME, AND COPOLYCARBONATE RESIN COMPRISING THE SAME
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A polyorganosiloxane compound, a method of preparing the same, and a copolycarbonate resin comprising the same are disclosed. Particularly, a copolycarbonate resin, which may be applied to a variety of applications, and in particular, comprises a polyorganosiloxane compound used as an impact modifier, a modifier, or a comonomer of a copolycarbonate resin and has improved mechanical properties such as low-temperature impact strength, is disclosed.
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Paragraph 0085; 0092
(2016/06/13)
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- DMF-mediated deprotection of bulky silyl esters under neutral and fluoride-free conditions
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Bulky TBDPS and TIPS carboxylic esters were efficiently cleaved by a green and mild protocol using only DMF-H2O (20:1) at 70 °C. The neutral conditions tolerate various common acid- and base-labile functionalities, including alkyl and aryl silyl ethers.
- Chen, Bo,Sun, Hui-Xia,Qin, Jian-Feng,Wang, Bing
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p. 253 - 255
(2016/01/12)
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- Acetylation of alcohols and phenols under solvent-free conditions using iron zirconium phosphate
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Iron zirconium phosphate (ZPFe) nanoparticles were found to function as an efficient catalyst for the acetylation of a wide range of alcohols and phenols using acetic anhydride, generating good to excellent yields under solvent-free conditions. The steric and electronic properties of various substrates had a significant influence on the reaction conditions required to achieve the acetylation. The catalyst used in the current study was characterized by inductively coupled plasma-optical emission spectrometry, X-ray diffraction, N2 adsorption-desorption, scanning electron microscopy, and transmission electron microscopy. These analyses revealed that the interlayer distance in the catalyst increased from 7.5 to 9.3 ? when Fe3+ was intercalated between the layers, whereas the crystallinity of the material was reduced. This nanocatalyst could also be recovered and reused at least six times without any discernible decrease in its catalytic activity. This new method for the acetylation of alcohols and phenols has several important advantages, including mild and environmentally friendly reaction conditions, as well as good to excellent yields and a facile work-up.
- Hajipour, Abdol R.,Karimi, Hirbod,Masti, Amir
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p. 595 - 602
(2015/09/28)
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- Discovery of Novel and Orally Bioavailable Inhibitors of PI3 Kinase Based on Indazole Substituted Morpholino-Triazines
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A new class of potent PI3Kα inhibitors is identified based on aryl substituted morpholino-triazine scaffold. The identified compounds showed not only a high level of enzymatic and cellular potency in nanomolar range but also high oral bioavailability. The three lead molecules (based on their in vitro potency) when evaluated further for in vitro metabolic stability as well as pharmacokinetic profile led to the identification of 26, as a candidate for further development. The IC50 and EC50 value of 26 is 60 and 500 nM, respectively, for PI3Kα enzyme inhibitory activity and ovarian cancer (A2780) cell line. The identified lead also showed a high level of microsomal stability and minimal inhibition activity for CYP3A4, CYP2C19, and CYP2D6 at 10 μM concentrations. The lead compound 26, demonstrated excellent oral bioavailability with an AUC of 5.2 μM at a dose of 3 mpk in mice and found to be well tolerated in mice when dosed at 30 mpk BID for 5 days.
- Dugar, Sundeep,Hollinger, Frank P.,Mahajan, Dinesh,Sen, Somdutta,Kuila, Bilash,Arora, Reena,Pawar, Yogesh,Shinde, Vaibhav,Rahinj, Mahesh,Kapoor, Kamal K.,Bhumkar, Rahul,Rai, Santosh,Kulkarni, Rakesh
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supporting information
p. 1190 - 1194
(2015/12/23)
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- Design, synthesis and docking studies of novel thienopyrimidine derivatives bearing chromone moiety as mTOR/PI3Kα inhibitors
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Two series of thienopyrimidine derivatives (10a-k, 16a-j) bearing chromone moiety were designed and synthesized. All the compounds were evaluated for inhibitory activity against mTOR kinase at a concentration of 10uM. Four selected compounds were further evaluated for the IC50 values against mTOR kinase, PI3Kα kinase and two cancer cell lines. Some of the target compounds exhibited moderate to excellent mTOR/PI3Kα kinase inhibitory activity and cytotoxicity. The most promising compound 16i showed good inhibitory activity against mTOR/PI3Kα kinase and good antitumor potency for H460 and PC-3 cell lines with IC50 values of 0.16 ± 0.03 μM, 2.35 ± 0.19 μM, 1.20 ± 0.23 μM and 0.85 ± 0.04 μM, which were 8.6, >5, 7.9 and 19.1 times more active than compound I (1.37 ± 0.07 μM, >10 μM, 9.52 ± 0.29 μM, 16.27 ± 0.54 μM), respectively. Structure-activity relationships (SARs) and docking studies indicated that the chromone moiety is necessary for the potent antitumor activity and cytotoxicity of these compounds. Substitution of the chromone moiety at the 6-position has a significant impact to the inhibitory activity, in particular a carboxylic acid group, produced the best potency.
- Zhu, Wufu,Chen, Chen,Sun, Chengyu,Xu, Shan,Wu, Chunjiang,Lei, Fei,Xia, Hui,Tu, Qidong,Zheng, Pengwu
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- Synthesis and Caco-2 cell permeability of N-substituted anthranilamide esters as ADP inhibitor in platelets
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Twelve N-substituted anthranilamide esters (1-5, 8, 9, 12, 13, and 15-17) were synthesized and evaluated for their ability to inhibit the in vitro aggregation by washed human platelets induced by adenosine 5′-diphosphate (10 μM). The antiplatelet activity of DL-n-butyl 5-hydroxy-N-(2-phenoxypropionyl)anthranilate (9, IC50 = 10.5 μM) was most active among the tested compounds and ethyl ester 8 (IC50 = 11.2 μM) showed the second most activity. DL-Ethyl and DL-n-butyl 5-(p-toluenesulfonyloxy)-N-(2-phenoxypropionyl)anthranilate (12, IC50 = 13.1 μM and 13, IC50 = 14.0 μM), DL-methyl N-(2-phenoxybutyryl)anthranilate (2, IC50 = 12.7 μM), DL-N-(2-phenoxypropionyl)anthranilic acid (5, IC50 = 13.7 μM) displayed lower antiplatelet activity than 8 and 9. Compound 5 was more active than methyl ester prodrug 1. n-Butyl 5-hydroxy-N-(4′-acetoxybenzoyl)anthranilate (15, IC50 = 28.3 μM) showed moderate activity. Compounds 1 (IC50 = 42.8 μM), 4 (IC50 = 56.7 μM), 16 (IC50 = 51.0 μM), and 17 (IC50 = 49.8 μM) exhibited low antiplatelet activity. Methyl N-phenoxyacetylanthranilate (3, IC50 = 78.0 μM) showed the lowest antiplatelet activity. The compounds with branched alkyl chain (2 and 5) were more active than compounds with straight chain (3 and 4). The apparent permeability coefficient (Papp, cm/s) values of compounds 2 and 9 were determined as 45.34 ± 4.67 and 33.17 ± 5.15 × 10-6 cm/s by Caco-2 cell permeability assay.
- Kim, Sohee,Shin, Beom Soo,Ma, Eunsook
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p. 1147 - 1156
(2015/02/19)
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- METHOD OF PRODUCING BENZOIC ACID
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PROBLEM TO BE SOLVED: To provide a novel synthesis method in the production of a benzoic acid and an industrially suitable production method using main materials derived from nonfossil resources. SOLUTION: This invention provides a method of producing a benzoic acid represented by formula (II), comprising the step of the ozonation of a compound represented by formula (I). COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0061; 0065; 0066; 0067; 0068
(2017/01/02)
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- Oxidative cleavage of olefins by in situ-generated catalytic 3,4,5,6-tetramethyl-2-iodoxybenzoic acid/oxone
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Oxidative cleavage of a variety of olefins to the corresponding ketones/carboxylic acids is shown to occur in a facile manner with 3,4,5,6-tetramethyl-2-iodobenzoic acid (TetMe-IA)/oxone. The simple methodology involves mere stirring of the olefin and catalytic amount (10 mol %) of TetMe-IA and oxone in acetonitrile-water mixture (1:1, v/v) at rt. The reaction mechanism involves initial dihydroxylation of the olefin with oxone, oxidative cleavage by the in situ-generated 3,4,5,6-tetramethyl-2-iodoxybenzoic acid (TetMe-IBX), and oxidation of the aldehyde functionality to the corresponding acid with oxone. Differences in the reactivities of electron-rich and electron-poor double bonds have been exploited to demonstrate chemoselective oxidative cleavage in substrates containing two double bonds.
- Moorthy, Jarugu Narasimha,Parida, Keshaba Nanda
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p. 11431 - 11439
(2015/02/05)
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- Molecular oxygen induced free radical oxythiocyanation of styrenes leading to α-oxothiocyanates
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A facile and efficient protocol of oxythiocyanation of styrenes with ammonium thiocyanate has been developed. The reaction proceeded at room temperature using oxygen as sole oxidant to afford the α-oxothiocyanates via radical pathway in moderate to good yields. This method is straightforward, green and cost-effective, requires no catalyst and additives.
- Liu, Kui,Li, Da-Peng,Zhou, Shao-Fang,Pan, Xiang-Qiang,Shoberu, Adedamola,Zou, Jian-Ping
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supporting information
p. 4031 - 4034
(2015/06/02)
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- Aerobic flow oxidation of alcohols in water catalyzed by platinum nanoparticles dispersed in an amphiphilic polymer
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We have developed a technique for the aqueous aerobic flow oxidation of alcohols in a continuous-flow reactor containing platinum nanoparticles dispersed on an amphiphilic polystyrene-poly(ethylene glycol) resin (ARP-Pt). Various primary and secondary alcohols including aliphatic, aromatic and heteroaromatic alcohols were efficiently oxidized within 73 seconds in a flowing aqueous system at 100-120°C under 40-70 bar of the system pressure to give the corresponding carboxylic acids and ketones, respectively, in up to 99% yield. Benzaldehydes could be also prepared selectively from benzyl alcohols by conducting the flow oxidation under the standard conditions in the presence of triethylamine. Moreover, a practical gram-scale synthesis of surfactants was realized in the aqueous aerobic continuous flow oxidation for 36-116 hours. This aerobic flow oxidation system provides a safe, clean, green, rapid and efficient practical method for oxidizing alcohols.
- Osako, Takao,Torii, Kaoru,Uozumi, Yasuhiro
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p. 2647 - 2654
(2015/02/05)
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- POLYMER-NSAID CONJUGATE
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The invention relates to polymer-drug conjugate for delivering a substituted alkanoic acid non-steroidal anti-inflammatory drug (NSAID). The invention also relates to drug delivery systems comprising the polymer-NSAID conjugate. The polymer-NSAID conjugates comprise a substituted alkanoic acid non-steroidal anti-inflammatory drug (NSAID) conjugated to a biodegradable polymer backbone by an ester linkage.
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Page/Page column 116; 117
(2014/01/17)
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- Acetylation of alcohols and phenols by zinc zirconium phosphate as an efficient heterogeneous catalyst under solvent-free conditions
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An efficient method for the acetylation of a wide range of alcohols as well as phenols with acetic anhydride in good to excellent yields under solvent-free conditions, using zinc zirconium phosphate as the catalyst was investigated. The catalyst was characterized by XRD, inductivity coupled plasma-optical emission spectroscopy, and scanning electron microscope. Products are easily isolated and the protocol is mild and green, compared to the existing methods. Graphical abstract: [Figure not available: see fulltext.]
- Hajipour, Abdol Reza,Karimi, Hirbod,Karimzadeh, Morteza
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p. 1461 - 1472
(2014/09/30)
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- Studies on the total synthesis of tenuifoliside B
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An efficient synthesis of tenuifoliside B, which shows potential cognitive improvement and cerebral protective effects that may be further developed to become an anti-AD lead compound, has been developed starting from commercial available starting materials. Regioselective introductions of acyl groups to the OH-3′ and OH-6 of sucrose play the key steps by metal chelate-directed acylation and Mitsunobu esterification, respectively.
- Wu, Yongjiang,Shi, Qiyuan,Lei, Houliang,Liu, Xuesong,Luan, Lianjun
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p. 3757 - 3761
(2014/05/20)
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- Acetylation of alcohols and phenols under solvent-free conditions using copper zirconium phosphate
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Copper zirconium phosphate nanoparticles have been used as an efficient catalyst for the acetylation of a wide range of alcohols and phenols with acetic anhydride in good to excellent yields under solvent-free conditions. The steric and electronic properties of the different substrates had a significant influence on the reaction conditions required to achieve the acetylation. The catalyst used in the current study was characterized by inductively-coupled plasma optical emission spectroscopy, energy dispersive spectroscopy, X-ray diffraction, N2 adsorption-desorption, scanning electron microscopy, and transmission electron microscopy. These analyses revealed that the interlayer distance in the catalyst increased from 7.5 to 8.0 ? when Cu2+ was intercalated between the layers, whereas the crystallinity of the material was reduced. This nanocatalyst could also be recovered and reused at least six times without any discernible decrease in its catalytic activity. This new method for the acetylation of alcohols and phenols has several key advantages, including mild and environmentally friendly reaction conditions, as well as good to excellent yields and a facile work-up.
- Hajipour, Abdol R.,Karimi, Hirbod
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p. 1982 - 1989
(2015/09/28)
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- Efficient preparation of novel phenolic surfactants for self-assembled monolayers
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Novel molecules have been synthesized that combine the phenolic nature of tannins and self-assembling properties of surfactants. These single-chain (C12) surfactants with potential biocompatibility have been synthesized with an ω-thiol or disulfide functionality, both commonly used anchors in self-assembly onto gold surfaces, using a modular route. Protecting groups for the phenol and thiol moieties played a key role for overcoming the challenges often associated with the purification of surfactants. The tasks of unmasking the thiol moiety and simultaneously deprotecting the acetyl protecting groups of the phenols were accomplished using sodium thiomethoxide. This modular route can be extended to synthesize other surfactants with the potential ability to form robust layers with biocompatible properties.
- Rajasingam, Arison,Schmidt, Rolf,Woo, Simon,DeWolf, Christine,Forgione, Pat
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p. 1066 - 1075
(2014/04/03)
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- Synthesis and characterization of Triad based rigid mesogenic diols derived from Hydroquinone and 4-hydroxybenzoic acid
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Triad based rigid mesogenic diols have been synthesized by four step synthesis method using protection-deprotecti method. Hydroquinone and 4-hydroxy benzoic acid have been used as starting materials. Synthesized diols have be characterized by IR, 1H and 13C NMR, and mass spectroscopic methods. Thermal properties have been determined b thermo gravimetric analysis method and degree of crystallinity have been measured by wide angle X-ray techniqu Substituted hydroquinones (methyl and chloro) have been used to study the effect of substitution on physical and therm properties. Synthesis of rigid mesogenic diol monomer using p-hydroxy benzoic acid and hydroquinone is reported, which a facile route. Hydrolysis of diacetate derivatives of rigid mesogenic diols is performed in good yields, even though tw types of ester groups present in the same moiety, aromatic and aliphatic. The experimental results reveal that hydroquino based rigid triad mesogenic diol have high thermal stability and degree of crystallinity as compared to methyl- and chlor substituted rigid triad mesogenic diols.
- Mulani, Khudbudin B.,Ganjave, Nitin V.,Chavan, Nayaku N.
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p. 591 - 596
(2014/06/23)
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- NOVEL TRIAZINE COMPOUNDS
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The present invention relates to novel triazine compounds of formula (1). The present invention also discloses compounds of formula I along with other pharmaceutical ac-ceptable excipients and use of the compounds to modulate the PI3K/ mTOR pathway
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Page/Page column 122
(2014/02/16)
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- Aromatic thermotropic polyesters based on 2,5-furandicarboxylic acid and vanillic acid
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This paper addresses a route to synthesize bio-based polymers with an aromatic backbone having a liquid crystalline (LC) phase in the molten state. The LC phase is employed to achieve uniaxial orientation during processing required in e.g. fiber spinning. For this purpose 2,5-furandicarboxylic acid (2,5-FDCA) and O-acetylvanillic acid (AVA), obtained from natural resources, are used as monomers. Similar to the 2,6-hydroxynapthoic acid used to perturb the crystalline packing of poly(oxybenzoate) in the Vectran series, these bio-based monomers are used to lower the crystal to liquid crystal transition temperature. Considering that the poly(oxybenzoate) can also be obtained from natural resources, the adopted route provides the unique possibility to synthesize bio-based polymers that can be used for high performance applications. To obtain the desired polymers, a synthetic route is developed to overcome the thermal instability of the 2,5-FDCA monomer. Experimental techniques, such as optical microscopy, FTIR spectroscopy, DSC, and TGA are employed to follow the polymerization, phase transitions and evaluate thermal stability of the synthesized polymers.
- Wilsens, Carolus H.R.M.,Noordover, Bart A.J.,Rastogi, Sanjay
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p. 2432 - 2439
(2014/05/20)
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- Synthesis and bioactivity of resveratrol analogues
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It has been reported that resveratrol enhanced SIRT1 expression and significantly mimicked calorie restriction by stimulating Sir2 which is the most homologic homologue of SIRT1 of mammalian. A series of novel resveratrol derivatives were designed and synthesized as novel SIRT1 activator candidates. These synthesized compounds were characterized by spectral (1H NMR) analysis and examined for their Sir2 activation against yeast parental strain-BY4743 at a concentration of 100 μM/L by Bioscreen C MBR machine. Several compounds showed a promising Sir2 activation activity compared with resveratrol. Meanwhile, the structure-activity relationships with Sirt2 activation activities were also discussed.
- Ao, Junli,Chen, Yuanmou,Xu, Xiaoling,Zhang, Xu,Yu, Yue,Yu, Peng,Hua, Erbing
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p. 2092 - 2098
(2014/06/09)
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- SuFEx-based synthesis of polysulfates
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High-molecular-weight polysulfates are readily formed from aromatic bis(silyl ethers) and bis(fluorosulfates) in the presence of a base catalyst. The reaction is fast and proceeds well under neat conditions or in solvents, such as dimethyl formamide or N-methylpyrrolidone, to provide the desired polymers in nearly quantitative yield. These polymers are more resistant to chemical degradation than their polycarbonate analogues and exhibit excellent mechanical, optical, and oxygen-barrier properties. High-molecular-weight polysulfates are readily formed from aromatic bis(silyl ethers) and bis(fluorosulfates) in the presence of a base catalyst. The polymers were obtained in nearly quantitative yield under neat conditions, they are more resistant to chemical degradation than their polycarbonate analogues and exhibit excellent mechanical, optical, and oxygen-barrier properties. BPA=bisphenol A.
- Dong, Jiajia,Sharpless, K. Barry,Kwisnek, Luke,Oakdale, James S.,Fokin, Valery V.
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supporting information
p. 9466 - 9470
(2014/11/07)
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- Penicillin inhibitors of purple acid phosphatase
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Purple acid phosphatases (PAPs) are binuclear metallohydrolases that have a multitude of biological functions and are found in fungi, bacteria, plants and animals. In mammals, PAP activity is linked with bone resorption and over-expression can lead to bone disorders such as osteoporosis. PAP is therefore an attractive target for the development of drugs to treat this disease. A series of penicillin conjugates, in which 6-aminopenicillanic acid was acylated with aromatic acid chlorides, has been prepared and assayed against pig PAP. The binding mode of most of these conjugates is purely competitive, and some members of this class have potencies comparable to the best PAP inhibitors yet reported. The structurally related penicillin G was shown to be neither an inhibitor nor a substrate for pig PAP. Molecular modelling has been used to examine the binding modes of these compounds in the active site of the enzyme and to rationalise their activities.
- Faridoon,Hussein, Waleed M.,Ul Islam, Nazar,Guddat, Luke W.,Schenk, Gerhard,McGeary, Ross P.
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supporting information; experimental part
p. 2555 - 2559
(2012/05/20)
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- Metal free: A novel and efficient aerobic oxidation of toluene derivatives catalyzed by N′, N″, Nprime;, -trihydroxyisocyanuric acid and dimethylglyoxime in PEG-1000-based dicationic acidic ionic liquid
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A non-metal catalytic system containing of N′, N″, Nprime;, -trihydroxyisocyanuric acid (THICA) and dimethylglyoxime (DMG) is described for the selective oxidation of toluene derivatives with dioxygen in PEG-1000-based dicationic acidic ionic liquid (PEG1000-DAIL). Several toluene derivatives were efficiently oxidized to corresponding acids under mild conditions. The oxidation followed a radical pathway and a possible mechanism was proposed. Both the catalyst and PEG1000-DAIL could be reused at least eight times without significantly decreasing the catalytic activity.
- Lu, Tingting,Mao, Yang,Yao, Kai,Xu, Jian,Lu, Ming
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p. 124 - 128
(2012/10/29)
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- Crystal structures of 4-(oxiran-2-ylmethoxy) benzoic acid and 4-acetoxybenzoic acid
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Compounds 4-(oxiran-2-ylmethoxy)benzoic acid (2) and 4-acetoxybenzoic acid (4) are synthesized by a new synthetic route and studied by X-ray crystallography. Compound 2 crystallizes in the monoclinic system, P21/n space group, a = 5.1209(2) A, b = 30.3429(16) A, c = 5.9153(3) A, β = 96.725(3)°, V = 912.81(8) A3, Z = 4. Compound 4 crystallizes in the triclinic system, P-1 space group, a = 7.3400(4) A, b = 8.0819(3) A, c = 15.6548(9) A, α = 85.754(3)°, β = 84.268(2)°, γ = 70.023(3)°, V = 867.63(8) A3, Z = 4. The crystal structure of 2 comprises two crystallographically independent molecules of the compound. In the crystal structures of 2 and 4, pairs of molecules form carboxyl dimers. Original Russian Text Copyright
- Obreza, A.,Perdih, F.
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p. 793 - 799,7
(2020/09/09)
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