Synthesis and evaluation of 2,5-di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles as anti-cancer agents

H D Gurupadaswamy; V Girish; C V Kavitha; Sathees C Raghavan; Shaukath Ara Khanum

doi:10.1016/j.ejmech.2013.02.040

Synthesis and evaluation of 2,5-di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles as anti-cancer agents

Eur J Med Chem. 2013 May:63:536-43. doi: 10.1016/j.ejmech.2013.02.040. Epub 2013 Mar 14.

Authors

H D Gurupadaswamy¹, V Girish, C V Kavitha, Sathees C Raghavan, Shaukath Ara Khanum

Affiliation

¹ Department of Chemistry, Yuvaraja's College Mysore, University of Mysore, Mysore 570 006, India.

PMID: 23535322
DOI: 10.1016/j.ejmech.2013.02.040

Abstract

A series of 2,5-di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles 9a-j were obtained via multistep synthesis from hydroxybenzophenones 4a-e. The cytotoxicity of compounds 9a-j was evaluated against human leukemia cell lines (K562 and CEM). The compounds exhibited moderate to good anti-cancer activity with compounds 9b and 9i having a chloro group exhibiting the best activity (IC50 = 10 μM). Compound 9i exhibited activity against both the cell lines and 9b only exhibited activity against CEM. Further, a lactate dehydrogenase (LDH) assay and DNA fragmentation studies of the compounds 9a-j were also performed.

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Cell Survival / drug effects
DNA Fragmentation / drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
Inhibitory Concentration 50
Intracellular Space / drug effects
Intracellular Space / enzymology
K562 Cells
L-Lactate Dehydrogenase / metabolism
Models, Chemical
Molecular Structure
Oxadiazoles / chemical synthesis*
Oxadiazoles / chemistry
Oxadiazoles / pharmacology*
Time Factors

Substances

Antineoplastic Agents
Oxadiazoles
L-Lactate Dehydrogenase