Affiliations 

  • 1 Institute of Chemical Sciences, Bahauddin Zakariya University, Multan 60800, Pakistan
  • 2 Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur 63100, Pakistan
  • 3 Natural and Medical Sciences Research Center, University of Nizwa, P.O. Box 33, Birkat Al Mauz, Nizwa 616, Oman
  • 4 Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan
  • 5 School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, 47500 Subang Jaya, Selangor, Malaysia
  • 6 Institute of Chemical Sciences, Bahauddin Zakariya University, Multan 60800, Pakistan; Department of Chemistry, The Woman University, Multan, Pakistan
  • 7 Department of Physics, University of Sargodha, Sargodha, Pakistan
  • 8 Institute of Chemical Sciences, Bahauddin Zakariya University, Multan 60800, Pakistan. Electronic address: zahidshafiq@bzu.edu.pk
Bioorg. Chem., 2019 03;84:372-383.
PMID: 30530108 DOI: 10.1016/j.bioorg.2018.11.053

Abstract

Xanthenone based hydrazone derivatives (5a-n) have been synthesized as potential α-glucosidase inhibitors. All synthesized compounds (5a-n) are characterized by their FTIR, 1H NMR, 13C NMR and HRMS, and in case of 5g also by X-ray crystallographic technique. The compounds unveiled a varying degree of α-glucosidase inhibitory activity when compared with standard acarbose (IC50 = 375.38 ± 0.12 µM). Amongst the series, compound 5l (IC50 = 62.25 ± 0.11 µM) bearing a trifluoromethyl phenyl group is found to be the most active compound. Molecular modelling is performed to establish the binding pattern of the more active compound 5l, which revealed the significance of substitution pattern. The pharmacological properties of molecules are also calculated by MedChem Designer which determines the ADME (absorption, distribution, metabolism, excretion) properties of molecules. The solid state self-assembly of compound 5g is discussed to show the conformation and role of iminoamide moiety in the molecular packing.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.