Synthesis of thio-heterocyclic analogues from Baylis-Hillman bromides as potent cyclooxygenase-2 inhibitors

Amlipur Santhoshi, Budde Mahendar, Saidulu Mattapally, Partha Sarathi Sadhu, Sanjay Kumar Banerjee, Vaidya Jayathirtha Rao

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11 Scopus citations


A series of thio-substituted pyrimidine, benzoxazole, benzothiazole and triazole analogues were synthesized from Baylis-Hillman bromides in a clean and efficient way. The synthesized twenty new compounds were subjected to in vitro COX-1 and COX-2 inhibitory activity. Majority of compounds found to be highly selective COX-2 inhibitor. Seven compounds (16e, 16f, 16k, 16l, 16m, 16r and 16s) displayed anti-inflammatory activity at micromolar concentrations with IC50 values for COX-2 inhibition ranging from 2.93 to 5.34 μM compared to reference drug whose IC50 is 2.66 μM. All these seven compounds had very little COX-1 inhibition property and thus are suitable candidates for anti-inflammatory drugs with less gastrointestinal side effect.

Original languageEnglish (US)
Pages (from-to)1952-1957
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Issue number8
StatePublished - Apr 15 2014

Bibliographical note

Funding Information:
The authors thank the Director, CSIR-Indian Institute of Chemical Technology, for encouragement. A.S. and P.S.S. acknowledge CSIR-New Delhi, B.M. acknowledge UGC-New Delhi and S.M. acknowledge ICMR-New Delhi for research fellowship. Origin-CSC-0108 and SMiLE–CSC112 projects are acknowledged for funding. S.K.B. is thankful to DBT for providing Ramalingaswami Fellowship.


  • Anti-inflammatory
  • Baylis-Hillman bromide
  • Cyclooxygenase
  • Thiobenzothiazole
  • Thiobenzotriazole
  • Thiobenzoxazole
  • Thiopyrimidine

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