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

作者信息

Mittal Shilpi, Malde Alpeshkumar, Selvam C, Arun K H S, Johar P S, Jachak Sanjay M, Ramarao P, Bharatam P V, Chawla H P S

机构信息

Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Sector-67, S.A.S. Nagar, Punjab-160062, India.

出版信息

Bioorg Med Chem Lett. 2004 Feb 23;14(4):979-82. doi: 10.1016/j.bmcl.2003.11.066.

DOI:10.1016/j.bmcl.2003.11.066

PMID:15013005

Abstract

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.

摘要