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

Mittal, Shilpi, Malde, A. K., Selvan, C., Arun, K. H. S., Johar, P. S., Jachak, Sanjay M., Ramarao, P., Bharatam, P. V. and Chawla, H. P. S. (2004) Synthesis and evaluation of S-4-(3-thienyl)phenyl-α-methylacetic acid. Bioorganic & Medicinal Chemistry Letters, 14 4: 979-982. doi:10.1016/j.bmcl.2003.11.066


Author Mittal, Shilpi
Malde, A. K.
Selvan, C.
Arun, K. H. S.
Johar, P. S.
Jachak, Sanjay M.
Ramarao, P.
Bharatam, P. V.
Chawla, H. P. S.
Title Synthesis and evaluation of S-4-(3-thienyl)phenyl-α-methylacetic acid
Journal name Bioorganic & Medicinal Chemistry Letters   Check publisher's open access policy
ISSN 1464-3405
0960-894X
Publication date 2004-02-01
Sub-type Article (original research)
DOI 10.1016/j.bmcl.2003.11.066
Volume 14
Issue 4
Start page 979
End page 982
Total pages 4
Place of publication Oxford
Publisher Pergamon Press/Elsevier
Language eng
Subject 030401 Biologically Active Molecules
030402 Biomolecular Modelling and Design
Abstract Herein we report an efficient procedure to synthesize S-4-(3-thienyl)phenyl-α-methylacetic acid, an enantiomerically pure intermediate of a recently approved nonsteroidal antiinflammatory cyclooxygenase inhibitor, atliprofen [methyl RS-4-(3-thienyl)phenyl-α-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. An efficient process for the preparation of S-4-(3-thienyl)phenyl-α-methylacetic acid, an enantiomerically pure intermediate of recently approved NSAID atliprofen is reported. The pharmacologically active isomer, S-4-(3-thienyl)phenyl-α-methylacetic acid was compared with S-ibuprofen by docking studies on COX enzyme structures followed by biological evaluations.
Keyword Arylpropionic acid
Docking
Cyclooxygenase
Q-Index Code C1
Additional Notes Other title: Bioorganic and medicinal chemistry letters(BIOSIS)

Document type: Journal Article
Sub-type: Article (original research)
Collections: Excellence in Research Australia (ERA) - Collection
School of Chemistry and Molecular Biosciences
 
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