Synthesis and evaluation of S-4-(3-thienyl)phenyl-α-methylacetic acid

被引：7

作者：

Mittal, S

Malde, A

Selvam, C

Arun, KHS

Johar, PS

Jachak, SM

Ramarao, P

Bharatam, PV

Chawla, HPS

机构：

[1] Natl Inst Pharmaceut Educ & Res, Dept Pharmaceut Technol, SAS Nagar 160062, Punjab, India

[2] Natl Inst Pharmaceut Educ & Res, Dept Med Chem, SAS Nagar 160062, Punjab, India

[3] Natl Inst Pharmaceut Educ & Res, Dept Pharmacol & Toxicol, SAS Nagar 160062, Punjab, India

[4] Natl Inst Pharmaceut Educ & Res, Dept Nat Prod, SAS Nagar 160062, Punjab, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2004年 / 14卷 / 04期

关键词：

arylpropionic acid; docking; cyclooxygenase;

D O I：

10.1016/j.bmcl.2003.11.066

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Herein we report an efficient procedure to synthesize S-4-(3-thienyl)phenyl-alpha-methylacetic acid, an enantiomerically pure intermediate of a recently approved nonsteroidal antiinflammatory cyclooxygenase inhibitor, atliprofen [methyl RS-4-(3-thienyl)phenyl-alpha-methylacetate]. The interactions of the active S-isomer of the acid were theoretically compared with those of S-ibuprofen through molecular docking studies using COX-1 and COX-2 protein structures. The results were corroborated by in vitro and in vivo studies. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：979 / 982

页数：4

共 18 条

[1] Putting chirality to work: The strategy of chiral switches [J].