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Journal of the Iranian Chemical Society

, Volume 15, Issue 11, pp 2441–2454 | Cite as

Synthesis, β-Glucuronidase Inhibition, and Molecular Docking Studies of 1,2,4-Triazole Hydrazones

  • Waqas Jamil
  • Darshana Kumari
  • Muhammad Taha
  • Muhammad Naseem Khan
  • Mohd Syukri Baharudin
  • Muhammad Ali
  • M. Kanwal
  • Muhammad Saleem Lashari
  • Khalid Muhammad Khan
Original Paper
  • 99 Downloads

Abstract

A series of 1,2,4-triazole hydrazones 1–25 has been synthesized and characterized using different spectroscopic techniques including FT-IR, 1H-NMR, and ESI MS spectrometry. The synthetic derivatives were evaluated for their β-glucuronidase enzyme inhibition properties. Among them, 17 compounds demonstrated potential inhibitory activity towards β-glucuronidase with IC50 values ranging between 2.50 and 53.70 µM. Compounds 1 having IC50 = 2.50 ± 0.01 µM was found to be the most active compound of the series and showed remarkable activity and found to be far more potent than the standard d-saccharic acid 1,4-lactone (IC50 = 48.4 ± 1.25 µM). Furthermore, the possible binding interaction of active compounds was explored by in silico studies. These compounds can be used for anti-diabetic drug development process.

Keywords

1,2,4-Triazole hydrazone β-Glucuronidase enzyme inhibition Anti-diabetic In silico studies 

Notes

Acknowledgements

The authors are thankful to University of Sindh, Jamshoro, and Higher Education Commission (HEC), Pakistan, for their financial support under “National Research Support Program for Universities”.

Compliance with ethical standards

Conflict of interest

There is no conflict of interest.

Supplementary material

13738_2018_1433_MOESM1_ESM.docx (249 kb)
Supplementary material 1 (DOCX 249 KB)

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Copyright information

© Iranian Chemical Society 2018

Authors and Affiliations

  • Waqas Jamil
    • 1
  • Darshana Kumari
    • 1
  • Muhammad Taha
    • 2
  • Muhammad Naseem Khan
    • 3
  • Mohd Syukri Baharudin
    • 4
  • Muhammad Ali
    • 7
  • M. Kanwal
    • 5
  • Muhammad Saleem Lashari
    • 6
  • Khalid Muhammad Khan
    • 5
  1. 1.Institute of Advance Research Studies in Chemical SciencesUniversity of SindhJamshoroPakistan
  2. 2.Department of Clinical Pharmacy, Institute for Research and Medical Consultations (IRMC)Imam Abdul Rehman Bin Faisal UniversityDammamSaudi Arabia
  3. 3.Department of Chemistry, COMSATS Institute of Information TechnologyUniversity RoadAbbottbadPakistan
  4. 4.Atta-ur-Rahman Institute for Natural Product DiscoveryUniversiti Teknologi MARA (UiTM)SelangorMalaysia
  5. 5.H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological SciencesUniversity of KarachiKarachiPakistan
  6. 6.Department of ChemistryUniversity of EducationLahorePakistan
  7. 7.UoN Chair of Oman’s Medicinal Plants and Marine Natural ProductsUniversity of NizwaNizwa 616Oman

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