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Letters in Drug Design & Discovery

Editor-in-Chief

ISSN (Print): 1570-1808
ISSN (Online): 1875-628X

Synthesis of 1,5-Diarylpyrazoles as Potential COX-2 Inhibitors with Nitric Oxide Releasing Ability

Author(s): Bolla Narasimha Rao, Meyyappan Muthuppalaniappan, Saketh Sriram Dinavahi, Srikant Viswanadha, Chandrakant Bagul, Kolupula Srinivas, Swaroop Kumar V. S. Vakkalanka, Krishnam Raju Atcha and Ahmed Kamal

Volume 10, Issue 7, 2013

Page: [594 - 603] Pages: 10

DOI: 10.2174/1570180811310070006

Price: $65

Abstract

A few celecosib like 1,5-diarylpyrazoles conjugated with nitric oxide (NO) donating nitrate ester group were synthesized and evaluated for their selective COX-2 inhibitory activity along with NO releasing ability of corresponding nitrate esters. Most of the synthesized compounds exhibited improved COX-2 inhibition when compared with the reference drug celecoxib. The nitrate ester derivatives (coxib prodrugs) 7 (nitrate ester of 1,5-diarylpyrazole with 2 carbon linker), and 9 (nitrate ester of 1,5-diarylpyrazole with 3 carbon linker), upon incubation in human whole blood were partly transformed into the corresponding alcohols 6, and 8 respectively. Molecular docking studies were performed on alcohol derivatives and revealed additional H-bond interactions compared to celecoxib.

Keywords: CINODs, COX-2 inhibition, Coxib prodrugs, 1, 5-Diarylpyrazoles, Nitrate esters, NO-Donors.


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