AgNO3 mediated C-N bond forming reaction: synthesis of 3-substituted benzothiazines as potential COX inhibitors

D. Rambabu, P V N S Murthy, K R S Prasad, Ajit Kandale, Girdhar Singh Deora, M. V. Basaveswara Rao, Manojit Pal

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13 Citations (Scopus)

Abstract

AgNO3 facilitated the intramolecular ring closure of o-(1-alkynyl)benzenesulfonamides via a regioselective C-N bond forming reaction leading to the formation of 3-substituted benzothiazine derivatives. A number of compounds were prepared in good yields by using this inexpensive and safe methodology. All the compounds synthesized were evaluated for their cyclooxygenase (COX) inhibiting properties in vitro. A number of compounds that do not contain an enolic hydroxyl group showed selectivities toward COX-2 over COX-1 inhibition. This was further supported by the predictive binding mode of two compounds with COX-1 and -2 proteins through molecular docking studies. 

Original languageEnglish
Pages (from-to)6577-6583
Number of pages7
JournalTetrahedron Letters
Volume53
Issue number48
DOIs
Publication statusPublished - 28 Nov 2012
Externally publishedYes

Keywords

  • AgNO
  • Benzenesulfonamides
  • Benzothiazine
  • COX
  • Docking

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