Synthesis and characterization of captopril derivatives

被引：2

作者：

Li, He-ping ^{[1
]}

Zhang, Juan-juan ^{[1
]}

Qin, Long ^{[1
]}

Zhao, Ming-dong ^{[1
]}

机构：

[1] Changsha Univ Sci & Technol, Coll Chem & Biol Engn, Changsha 410004, Hunan, Peoples R China

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 2013年 / 39卷 / 02期

基金：

中国国家自然科学基金;

关键词：

Captopril; Amino acid methyl ester; Synthesis; Acylation; ANGIOTENSIN-CONVERTING ENZYME; PEPTIDES; AMINES; CHAIN;

D O I：

10.1007/s11164-012-0584-z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

To develop more potential angiotensin converting enzyme (ACE) inhibitors, a series of captopril (Cap) derivatives were synthesized, including Cap-glycine methyl ester, Cap-l-alanine methyl ester, Cap-l-aspartic acid dimethyl ester, Cap-l-lysine methyl ester, Cap-O-acylisourea, acetyl captopril, and benzoyl captopril. The resulting products were characterized by IR and UV-visible spectroscopy and MS, which showed the desired products were successfully synthesized. This could serve as a guide for rational design of highly potent ACE inhibitors.

引用

页码：621 / 629

页数：9

共 21 条

[1] Catalyst-free chemoselective N-tert-butyloxycarbonylation of amines in water [J].

Chankeshwara, Sunay V. ;

Chakraborti, Asit K. .

ORGANIC LETTERS, 2006, 8 (15) :3259-3262

[2] MOLECULAR-CLONING OF HUMAN TESTICULAR ANGIOTENSIN-CONVERTING ENZYME - THE TESTIS ISOZYME IS IDENTICAL TO THE C-TERMINAL HALF OF ENDOTHELIAL ANGIOTENSIN-CONVERTING ENZYME (POLYMERASE CHAIN-REACTION ALTERNATIVE SPLICING) [J].

EHLERS, MRW ;

FOX, EA ;

STRYDOM, DJ ;

RIORDAN, JF .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1989, 86 (20) :7741-7745

[3] Synthesis and biological evaluation of N-mercaptoacylproline and N-mercaptoacylthiazolidine-4-carboxylic acid derivatives as leukotriene A4 hydrolase inhibitors [J].

Enomoto, Hiroshi ;

Morikawa, Yuko ;

Miyake, Yurika ;

Tsuji, Fumio ;

Mizuchi, Maki ;

Suhara, Hiroshi ;

Fujimura, Ken-ichi ;

Horiuchi, Masato ;

Ban, Masakazu .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (16) :4529-4532

[4]

FitzGerald RJ, 2000, BRIT J NUTR, V84, pS33

[5] A simple two-step approach for introducing a protected diaminedithiol chelator during solid-phase assembly of peptides [J].

Gariépy, J ;

Rémy, S ;

Zhang, XG ;

Ballinger, JR ;

Bolewska-Pedyczak, E ;

Rauth, M ;

Bisland, SK .

BIOCONJUGATE CHEMISTRY, 2002, 13 (03) :679-684

[6] Facile catalyzed acylation of alcohols, phenols, amines and thiols based on ZrOCl28H2O and acetyl chloride in solution and in solvent-free conditions [J].

Ghosh, R ;

Maiti, S ;

Chakraborty, AJ .

TETRAHEDRON LETTERS, 2005, 46 (01) :147-151

[7] Analogues of thiolactomycin as potential antimalarial agents [J].

Jones, SM ;

Urch, JE ;

Kaiser, M ;

Brun, R ;

Harwood, JL ;

Berry, C ;

Gilbert, IH .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (19) :5932-5941

[8] Synthesis and evaluation of novel 2-butyl-4-chloro-1-methylimidazole embedded chalcones and pyrazoles as angiotensin converting enzyme (ACE) inhibitors [J].

Kantevari, Srinivas ;

Addla, Dinesh ;

Bagul, Pankaj K. ;

Sridhar, Balasubramanian ;

Banerjee, Sanjay K. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (16) :4772-4781

[9] Bioactive proteins and peptides from food sources. Applications of bioprocesses used in isolation and recovery [J].

Kitts, DD ;

Weiler, K .

CURRENT PHARMACEUTICAL DESIGN, 2003, 9 (16) :1309-1323

[10] Preparation of β-amino-α-mercapto acids and amides:: stereocontrolled syntheses of 2′-sulfur analogues of the taxol C-13 side chain, both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine [J].

Lee, SH ;

Qi, X ;

Yoon, JY ;

Nakamura, K ;

Lee, YS .

TETRAHEDRON, 2002, 58 (14) :2777-2787

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