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Medicinal Chemistry Research

, Volume 24, Issue 7, pp 2960–2971 | Cite as

Discovery of Rimonabant and its potential analogues as anti-TB drug candidates

  • J. M. GajbhiyeEmail author
  • N. A. More
  • Manoj D. Patil
  • R. Ummanni
  • S. S. Kotapalli
  • P. Yogeeswari
  • D. Sriram
  • V. H. Masand
Original Research

Abstract

Rimonabant and its analogues have been synthesized in moderate to good yields using a simple synthetic route. All the newly synthesized compounds were subjected to in vitro screening against M. tuberculosis and M. smegmatis. The most potent analogue JMG-14 exhibits MIC value of 3.13 compared to 3.25 and 50 µg/ml for ethambutol and pyrazinamide, respectively. The molecular docking reveals that pyrazole ring, number and position of halogen atoms play a crucial role in deciding interactions with MTCYP-121. These findings open up a new avenue in the search of potent anti-TB drugs with rimonabant and its novel analogue JMG-14 as lead molecules.

Graphical Abstract

Keywords

Rimonabant Diaryl pyrazoles Tuberculosis Mycobacterium tuberculosis H37Rv MTCYP-121 

Notes

Acknowledgments

JMG gratefully acknowledges CSIR-OSDD, CSIR-ORIGIN and DST-SERB, for the financial support.

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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • J. M. Gajbhiye
    • 1
    Email author
  • N. A. More
    • 1
  • Manoj D. Patil
    • 1
  • R. Ummanni
    • 2
  • S. S. Kotapalli
    • 2
  • P. Yogeeswari
    • 3
  • D. Sriram
    • 3
  • V. H. Masand
    • 4
  1. 1.Division of Organic ChemistryCSIR-National Chemical LaboratoryPuneIndia
  2. 2.Centre for Chemical BiologyIndian Institute of Chemical TechnologyHyderabadIndia
  3. 3.Tuberculosis Drug Discovery Laboratory, Pharmacy GroupBirla Institute of Technology and Science, PilaniHyderabadIndia
  4. 4.Department of ChemistryVidyaBharati CollegeAmravatiIndia

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