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Synthesis of new 1,3,4-oxadiazole and benzothiazolylthioether derivatives of 4-arylmethylidene-3-substituted-isoxazol-5(4H)-one as potential antimycobacterial agents

  • Abhijit P. Chavan
  • Rujuta R. Deshpande
  • Nandkumar A. Borade
  • Abhijit Shinde
  • Pravin C. MhaskeEmail author
  • Dhiman Sarkar
  • Vivek D. BobadeEmail author
Original Research
  • 5 Downloads

Abstract

A new series of 4-[(substituted benzylidene)-3-[(5-(pyridine-4-yl)-1,3,4-oxadiazole-2-ylthio)-methyl]isoxazol-5(4H)-one (6a–g) and 4-(substituted benzylidene)-3-((benzo[d]thiazol-2-ylthio)methyl)isoxazol-5(4H)-one (8a–g) was synthesized. All the synthesized compounds were screened for antitubercular activity against Mycobacterium tuberculosis H37Ra (ATCC 25177) and Mycobacterium bovis BCG (ATCC 35743) and antibacterial activity against Escherichia coli (NCIM 2576), Pseudomonas flurescence (NCIM 2059), Staphylococcus aureus (NCIM 2602), Bacillus subtilis (NCIM 2162). Amongst the synthesized 1,3,4-oxadiazole and benzothiazoyl thioether derivatives, compounds 6b and 8b showed excellent antimycobacterial activity and compounds 6b, 8a, 8b, and 8d showed excellent antibacterial activity against all tested antibacterial strains. The synthesized compounds were further evaluated for their cytotoxic activity against the HCT 116 and HeLa cancer cell lines. The 1,3,4-oxadiazole and benzothiazoyl thioether derivatives 6a–g and 8a–g did not show cytotoxicity.

Keywords

Isoxazol-5(4H)-one 1,3,4-Oxadiazole Benzothiazol Thioeteher Antitubercular activity Antibacterial activity 

Notes

Acknowledgements

The authors would like to express sincere thanks to Savitribai Phule Pune University, Pune and DST, New Delhi for providing financial assistance. CIF Savitribai Phule Pune University is also acknowledged for the spectral analysis.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

44_2019_2420_MOESM1_ESM.doc (1.1 mb)
Supplementary Information

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of Chemistry, Sir Parashurambhau CollegeAffiliated to Savitribai Phule Pune UniversityPuneIndia
  2. 2.Department of Chemistry, HPT Arts and RYK Science CollegeAffiliated to Savitribai Phule Pune UniversityNasikIndia
  3. 3.Department of Zoology, Modern College of Arts, Science and CommerceAffiliated to Savitribai Phule Pune UniversityPuneIndia
  4. 4.Department of Chemistry, Kirti M. Doongursee CollegeAffiliated to University of MumbaiMumbaiIndia
  5. 5.CombiChemBio Resource CentreCSIR-National Chemical LaboratoryPuneIndia

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