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Synthesis and bioevaluation of α,α’-bis(1H-1,2,3-triazol-5-ylmethylene) ketones

  • Tejshri R. Deshmukh
  • Vagolu S. Krishna
  • Dharmarajan Sriram
  • Jaiprakash N. Sangshetti
  • Bapurao B. ShingateEmail author
Original Paper
  • 31 Downloads

Abstract

Curcumin is an active component of turmeric that has poor solubility, stability and bioavailability. The monocarbonyl curcumin analogues were modified from curcumin to achieve more stable and active compounds as compared to curcumin. Therefore, we have designed and synthesized a library of 18 compounds of α,α’-bis(1H-1,2,3-triazol-5-ylmethylene) ketones (8ao) and evaluated them for their in vitro antitubercular and antioxidant activities against their respective strains. Results of biological activities reveal that some of the compounds from the series showed good antitubercular as well as antioxidant activities. The compound 8l was found as the most active antitubercular agent with MIC value 3.125 µg/mL, against Mtb H37Rv. Moreover, the compounds, 8c, 8d, 8e and 8g, also showed potent antitubercular activity. The compounds 8e and 8m displayed potent antioxidant activities with IC50 values 15.60 and 15.49 µg/mL, respectively. In support of the bioactivities, in silico ADME properties’ prediction has also been carried out in this study.

Graphic Abstract

Keywords

α,α’-bis(1H-1,2,3-triazol-5-ylmethylene) ketones Curcumin Antitubercular activity Antioxidant activity 

Notes

Acknowledgements

The authors are thankful to the Head, Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad-431 004, India for providing laboratory facility.

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Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2019

Authors and Affiliations

  • Tejshri R. Deshmukh
    • 1
  • Vagolu S. Krishna
    • 2
  • Dharmarajan Sriram
    • 2
  • Jaiprakash N. Sangshetti
    • 3
  • Bapurao B. Shingate
    • 1
    Email author
  1. 1.Department of ChemistryDr. Babasaheb Ambedkar Marathwada UniversityAurangabadIndia
  2. 2.Department of PharmacyBirla Institute of Technology and Science-PilaniHyderabadIndia
  3. 3.Department of Pharmaceutical ChemistryY. B. Chavan College of PharmacyAurangabadIndia

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