- Simple Synthesis of Amides via Their Acid Chlorides in Aqueous TPGS-750-M
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The technology of surfactant chemistry is employed for amide bond construction via the reaction of acyl chlorides with amines in 2 wt % TPGS-750-M aqueous solution. Specifically, this highly efficient method enables a chromatography-free scalable process and recycling of the TPGS-750-M solution.
- Shi, Min,Ye, Ning,Chen, Wei,Wang, Hui,Cheung, Chiming,Parmentier, Michael,Gallou, Fabrice,Wu, Bin
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supporting information
p. 1543 - 1548
(2020/11/23)
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- Structure–activity relationship investigation of tertiary amine derivatives of cinnamic acid as acetylcholinesterase and butyrylcholinesterase inhibitors: compared with that of phenylpropionic acid, sorbic acid and hexanoic acid
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In the present investigation, 48 new tertiary amine derivatives of cinnamic acid, phenylpropionic acid, sorbic acid and hexanoic acid (4d–6g, 10d–12g, 16d–18g and 22d–24g) were designed, synthesized and evaluated for the effect on AChE and BChE in vitro. The results revealed that the alteration of aminoalkyl types and substituted positions markedly influences the effects in inhibiting AChE. Almost of all cinnamic acid derivatives had the most potent inhibitory activity than that of other acid derivatives with the same aminoalkyl side chain. Unsaturated bond and benzene ring in cinnamic acid scaffold seems important for the inhibitory activity against AChE. Among them, compound 6g revealed the most potent AChE inhibitory activity (IC50 value: 3.64 μmol/L) and highest selectivity over BChE (ratio: 28.6). Enzyme kinetic study showed that it present a mixed-type inhibition against AChE. The molecular docking study suggested that it can bind with the catalytic site and peripheral site of AChE.
- Gao, Xiaohui,Tang, Jingjing,Liu, Haoran,Liu, Linbo,Kang, Lu,Chen, Wen
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p. 519 - 524
(2018/02/27)
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- INHIBITORS OF DIHYDROCERAMIDE DESATURASE FOR TREATING DISEASE
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Disclosed herein are dihydroceramide desaturase 1 (Des1) inhibitor compounds and compositions, which are useful in the treatment of diseases, such as metabolic, cardiovascular, fibrotic, autoimmune/chronic inflammatory diseases, cystic fibrosis, various cancers, neurodegenerative diseases, lipid storage disorders, and ischemia/reperfusion injury, where inhibition of Des1 is expected to be therapeutic to a patient. Methods of inhibition of Des1 activity in a human or animal subject are also provided.
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Paragraph 00245; 00259
(2018/09/11)
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- Ligand- and Additive-Controlled Pd-Catalyzed Aminocarbonylation of Alkynes with Aminophenols: Highly Chemo- and Regioselective Synthesis of α,β-Unsaturated Amides
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This work describes the chemo- and regioselective direct aminocarbonylation of alkynes and aminophenols to form hydroxy-substituted α,β-unsaturated amides in good to excellent yields. The latter are valuable compounds in pharmaceuticals and natural products. By a simple choice of different ligands and additives, branched or linear isomers could be selectively formed in excellent regioselectivity. Using a combination of boronic acid and 5-chlorosalicylic acid ( BCSA ) as the additives, linear amides were obtained in high yields and selectivities using 1,2-bis(di-tert-butylphosphinomethyl)benzene (DTBPMB) as the ligand. On the other hand, branched amides could be approached by introducing 1,3-bis(diphenylphosphino)propane as the ligand and p-TsOH·H2O as the additive. In addition to the hydroxyl group, other functional substituents, such as carboxyl and vinyl groups, could also be tolerated using this method. As an application of this strategy, the natural product avenanthramide A could be synthesized directly in 84% yield and in 99% regioselectivity via the carbonylation of 2-amino-5-hydroxybenzoic acid and 4-ethynylphenol. Further studies show that the ligands and the additives are keys to good yields and selectivities.
- Sha, Feng,Alper, Howard
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p. 2220 - 2229
(2017/08/09)
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- Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors
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Four series of acid amides were synthesized, and through measurement using a fluorogenic substrate assay with human recombinant MMP-1, MMP-2 and MMP-9, compound 3f showed considerable inhibitory activities against MMP-2, MMP-9 and the best selectivity over MMP-1. Preliminary structure-activity relationship analysis indicated that caffeic acid amides with electron-donating groups at para-position of amino phenyl group showed better inhibitory activities and selectivity than those with electron-withdrawing groups, and the presence of adjacent dihydroxy in the caffeoyl group was very important for the MMP-2 and MMP-9 inhibitory activities.
- Shi, Zhi-Hao,Li, Nian-Guang,Shi, Qian-Ping,Tang, Hao,Tang, Yu-Ping,Li, Wei,Yin, Lian,Yang, Jian-Ping,Duan, Jin-Ao
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p. 1206 - 1211
(2013/03/14)
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- Synthesis and structure of N-Aryl(phenoxy, benzylidene)acetyl-1,4- benzoquinone monoimines
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New N-aryl(phenoxy, benzylidene)acetyl-1,4-benzoquinone monoimines were synthesized by reaction of aminophenols with arylacetyl, phenoxyacetyl, and cinnamoyl chlorides in dimethylformamide-acetic acid (1 : 3) in the presence of anhydrous sodium acetate. Structural parameters of the products and their probable biological activity were determined. Pleiades Publishing, Ltd., 2012.
- Avdeenko,Konovalova,Vasil'eva,Shishkin,Palamarchuk,Baumer
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p. 1309 - 1319
(2013/02/22)
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- Synthesis, antimicrobial, and QSAR studies of substituted benzamides
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A series of new substituted benzamides were synthesized and tested in vitro for their antibacterial activity against Gram-positive and Gram-negative bacteria and as well for antifungal activity. The compounds 8i and 9 showed better activity among the different benzamides synthesized. The structural characteristics governing antibacterial activities of substituted benzamides were studied using QSAR methodology. The results showed that the antimicrobial activity could be modeled using the topological descriptors, molecular connectivity indices (2χv and 2χ) and Kiers shape index (κα1). The low residual activity and high cross-validated r2 values (rcv2) observed indicated the predictive ability of the developed QSAR models.
- Kumar, Anil,Narasimhan, Balasubramanian,Kumar, Devinder
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p. 4113 - 4124
(2008/03/11)
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- Synthesis and antiarrhythmic and parasympatholytic properties of substituted phenols. 3. Modifications to the linkage region (region 3)
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As part of a continuing program of systematically modifying the structure of the class I antiarrhythmic drug changrolin, we synthesized 15 analogues in which the linkage between the two aromatic regions was altered. High antiarrhythmic activity and low parasympatholytic activity was found when the linkage region, designated region 3, contained a carbonyl moiety, including ketones, amides, and ureas. Secondary amides were superior to tertiary amides, while amide reversal resulted in no change in activities. One compound in this series, 2,6-bis(1-pyrrolidinyl-methyl)-4-benzamidophenol (ACC-9358), is undergoing preclinical evaluations.
- Stout,Matier,Barcelon-Yang,Reynolds,Brown
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p. 295 - 298
(2007/10/02)
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- Spectrophotometric and Titrimetric Determination of Carboxylic Acid Anhydrides
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Two redox methods are described for the determination of carboxylic acid anhydrides involving reaction with either an excess of 4-aminophenol or a measured but excessive amount of sulfanilamide and photometric titration of N-acyl-4-aminophenol with 2-iodylbenzoate by measuring the absorbance of orange-red product at 444 nm or the residual amount of sulfanilamide is determined by titration with chloramine-T in the presence of acidified potassium bromide using methyl red as visual indicator.Mixtures of certain anhydrides have also been analyzed by the 2-iodylbenzoate method.The methods are rapid, precise, and accurate.No correlation is needed if carboxylic and mineral acids are also present.Carboxylic acid chlorides also react quantitatively.
- Verma, Krishna K.,Tyagi, Pramila
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p. 2157 - 2160
(2007/10/02)
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