Synthesis of novel 2-mercaptobenzoxazole based 1,2,3-triazoles as inhibitors of proinflammatory cytokines and suppressors of COX-2 gene expression

Saqlain Haider, Mohammad Sarwar Alam, Hinna Hamid, Syed Shafi, Abhijeet Dhulap, Firasat Hussain, Perwez Alam, Sadiq Umar, M. A.Q. Pasha, Sameena Bano, Syed Nazreen, Yakub Ali, Chetna Kharbanda

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

A library of novel bis-heterocycles containing 2-mercaptobenzoxazole based 1,2,3-triazoles has been synthesized using click chemistry approach. The compound 4 exhibited the most potent in vivo anti-inflammatory activity with 66.66% and 61.11% inhibition in comparison to celecoxib which showed 72.22% and 65.55% inhibition after 3 h and 5 h respectively. The compounds 4 and 9 suppressed the COX-2 gene expression by 0.94 and 0.79 fold and exhibited a selective index (COX-1/COX-2) of 64.79 and 66.47 respectively in comparison to celecoxib (SI value of 75.56). The in silico molecular docking studies showed the interactions of these molecules with Tyr-59, Tyr-119 and Gly-121. When compared with the standard drug celecoxib, compounds 4, 5, 7, 9 and 16 did not cause any gastric ulceration.

Original languageEnglish (US)
Pages (from-to)204-217
Number of pages14
JournalEuropean Journal of Medicinal Chemistry
Volume81
DOIs
StatePublished - Jun 23 2014

Bibliographical note

Funding Information:
The authors thank Dr. G.N. Qazi, Vice-Chancellor, Jamia Hamdard for providing necessary facilities to the Department of Chemistry. One of the authors (SH) is also thankful to Council of Scientific and Industrial Research (CSIR), New Delhi for the award of senior research fellowship.

Keywords

  • Antinociceptive
  • Crystallography
  • Cyclooxygenase
  • Gene expression
  • Molecular docking

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