Synthesis and Antibacterial Studies of Some Novel 2-(Coumarin-3-yl)-5-mercapto-1,3,4-oxadiazoles Containing 2,4,6-Trisubstituted s-Triazine Derivatives

Abstract

A new series of 2-(coumarin-3-yl)-5-mercapto-1,3,4-oxadiazoles based on various aryl thiourea/ureas incorporating a 1,3,5-s-triazine moiety is reported. The components of this series have been obtained by the reaction of cyanuric chloride (1) with 2-(coumarin-3-yl)-5-mercapto-1,3,4-oxadiazole (2). The prepared 2-{(coumarin-3-yl-1,3,4-oxadiazolyl)-5-thio}-4,6-dichloro-s-triazine (3) was subsequently treated with morpholine (4) to form 2-{(coumarin-3-yl-1,3,4-oxadiazolyl)-5-thio}-4-(morpholino)-6-chloro-s-triazine (5). This was further treated with various substituted aryl urea/thioureas (6a–k/7a–k) to afford the title compounds 8a–k and 9a–k, which were and tested for their antibacterial activity (MIC) against different microorganisms. The structures of the novel synthesized compound have been established on the basis of ¹H NMR and FT-IR data together with elemental analysis.

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Keywords:

• Antibacterial activity (MIC)
• aryl urea/thiourea
• 2-(coumarin-3-yl)-5-mercapto- 1,3,4-oxadiazole
• 1,3,5-s-triazine

Acknowledgments

The authors are very thankful to Prof. Dr. K. R. Desai, Head, Department of Chemistry, Veer Narmad South Gujarat University, Surat, India, for providing the research facilities; one of the authors (A.C.P.) would like to thank Dr. S. Chattopadhyay, Head, Bioorganic Division, B.A.R.C. Mumbai for ¹H NMR spectra and Prof. Dr. S. K. Menon, Gujarat University, Ahmedabad, India, for IR spectral studies.