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Bioorg Chem. 2019 Mar;84:372-383. doi: 10.1016/j.bioorg.2018.11.053. Epub 2018 Nov 30.

Xanthenone-based hydrazones as potent α-glucosidase inhibitors: Synthesis, solid state self-assembly and in silico studies.

Author information

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.

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.

KEYWORDS:

Acarbose; Hydrazone; Molecular docking study; Xanthenone; α-glucosidase inhibitor

PMID:
30530108
DOI:
10.1016/j.bioorg.2018.11.053
[Indexed for MEDLINE]

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