Medicinal Chemistry Research

, Volume 21, Issue 10, pp 3119–3132 | Cite as

Synthesis of novel 3-(5-sulfanyl-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one condensed s-triazinyl piperazines and piperidines as antimicrobial agents

  • Rahul V. Patel
  • Amit B. Patel
  • Premlata Kumari
  • Kishor H. Chikhalia
Original Research
First Online:
Received:
Accepted:

Abstract

Synthesis and antimicrobial activity of a new series of 3-(5-sulfanyl-1,3,4-oxadiazol-2-yl)-2H-chromen-2-ones based on various substituted piperazines and piperidines incorporating a 1,3,5-triazine moiety are reported in this article. 3-{5-[(4,6-dichloro-1,3,5-triazin-2-yl)sulfanyl]-1,3,4-oxadiazol-2-yl}-2H-chromen-2-one 3 was obtained by the reaction of 2,4,6-trichloro-1,3,5-triazine 1 with 3-(5-sulfanyl-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one 2 which was obtained by following the method reported in the literature. Intermediate 3 was then condensed with 8-hydroxyquinoline 4 to form 3-(5-{[4-chloro-6-(quinolin-4-yloxy)-1,3,5-triazin-2-yl]sulfanyl}-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one 5. This was further treated with various substituted piperazines and piperidines to obtain the title compounds 7a–u, which were then subjected to determine their in vitro biological efficacy against bacterial and fungal strains as two Gram-positive bacteria (S. aureus, B. cereus), six Gram-negative bacteria (E. coli, P. aeruginosa, K. pneumoniae, S. typhi, P. vulgaris, and S. flexneria) and two fungal species (A. niger, and C. albicans) with an intent to develop novel class of antimicrobial agents. The results indicate that some of the novel s-triazines have noteworthy activity in MIC (μg/ml) and zone of inhibition (mm) indicating potential leads for further drug discovery study. All the final compounds were structurally elucidated on the basis of IR, 1H NMR, 13C NMR, 19F NMR spectroscopy, and elemental analysis.

Keywords

3-(5-Sulfanyl-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one 2,4,6-Trichloro-1,3,5-triazine Antimicrobial activity 
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Notes

Acknowledgments

The authors are thankful to the faculty of the Department of Applied Chemistry, S. V. National Institute of Technology, Surat for providing the scholarship, encouragement, and facilities.

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Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Rahul V. Patel
    • 1
  • Amit B. Patel
    • 1
  • Premlata Kumari
    • 1
  • Kishor H. Chikhalia
    • 2
  1. 1.Department of Applied ChemistryS. V. National Institute of TechnologySuratIndia
  2. 2.Department of Chemistry, School of ScienceGujarat UniversityAhmedabadIndia

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