Synthesis of novel indenoquinoxaline derivatives as potent α-glucosidase inhibitors

Madiha Sahar Khan; Munawar Ali Munawar; Mohammad Ashraf; Umber Alam; Athar Ata; Abdullah Mohamed Asiri; Samina Kousar; Misbahul Ain Khan

doi:10.1016/j.bmc.2013.12.024

Synthesis of novel indenoquinoxaline derivatives as potent α-glucosidase inhibitors

Bioorg Med Chem. 2014 Feb 1;22(3):1195-200. doi: 10.1016/j.bmc.2013.12.024. Epub 2013 Dec 21.

Authors

Madiha Sahar Khan¹, Munawar Ali Munawar², Mohammad Ashraf³, Umber Alam³, Athar Ata⁴, Abdullah Mohamed Asiri⁵, Samina Kousar¹, Misbahul Ain Khan⁶

Affiliations

¹ Institute of Chemistry, University of the Punjab, Lahore 54590, Pakistan.
² Institute of Chemistry, University of the Punjab, Lahore 54590, Pakistan. Electronic address: mamunawar.chem@pu.edu.pk.
³ Department of Biochemistry and Biotechnology, The Islamia University of Bahawalpur, Bahawalpur 63100, Pakistan.
⁴ Department of Chemistry, University of Winnipeg, 515 Portage Avenue, Winnipeg MB R3B 2E9, Canada.
⁵ Centre of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia.
⁶ Institute of Chemistry, University of the Punjab, Lahore 54590, Pakistan; Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur 63100, Pakistan.

PMID: 24398385
DOI: 10.1016/j.bmc.2013.12.024

Abstract

A series of new N-(11H-Indeno[1,2-b]quinoxalin-11-ylidene)benzohydrazide derivatives (3a-3p) were synthesized and evaluated for their α-glucosidase inhibitory activity. The synthesized compounds 3d, 3f, 3g, 3k, 3n, 3p and 4 showed significant α-glucosidase inhibitory activity as compared to acrabose, a standard drug used to treat type II diabetes. Structures of the synthesized compounds were determined by using FT-IR, (1)H NMR, (13)C NMR, mass spectrometry and elemental analysis techniques.

Keywords: 1,2-Di(11H-indeno[2,1-b]quioxalin-11-ylidene)hydrazine; 11H-Indeno[1,2-b]quinoxalin-11-one; N-(11H-Indeno[1,2-b]quinoxalin-11-ylidene)benzohydrazides; α-Glucosidase inhibitors.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acarbose / pharmacology
Chemistry Techniques, Synthetic
Enzyme Inhibitors / chemical synthesis
Enzyme Inhibitors / chemistry*
Enzyme Inhibitors / pharmacology*
Glycoside Hydrolase Inhibitors*
Hypoglycemic Agents / pharmacology
Imidazoles / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Spectroscopy, Fourier Transform Infrared
Structure-Activity Relationship

Substances

Enzyme Inhibitors
Glycoside Hydrolase Inhibitors
Hypoglycemic Agents
Imidazoles
oxaline
Acarbose