Design, synthesis and characterization of novel amine derivatives of 5-[5-(chloromethyl)-1, 3, 4-oxadiazol-2-yl]- 2-(4-fluorophenyl)-pyridine as a new class of anticancer agents

Adimule Vinayak, Medapa Sudha, Kumar S. Lalita

Abstract


A linear strategy was adopted in synthesizing the novel amine derivatives 7(a-h) of 5-[5-
(chloromethyl)-1, 3, 4-oxadiazol-2-yl]-2-(4-fluorophenyl)-pyridine (6) and screened these compounds for in vitro
anticancer activity against three human cancer cell lines (HeLa,Caco-2 and HepG2). The synthesised novel
compounds were characterized by 1H NMR, MS and 13C NMR spectroscopic evidences. Microwave irradiation of
compound (5) in presence of chloroacetyl chloride and phosphoryl oxychloride yielded the dehydrated cyclized key
intermediate 5-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-2-(4-fluorophenyl)-pyridine which upon treatment with
various primary or secondary amines (a-h) resulted into the corresponding amine derivatives. The IC50 values of the
final compounds were compared with that of 5-fluorouracil (5-FU) taken as the standard. Compounds 7a and 7d were
found to be highly cytotoxic against HepG2 cell lines with IC50 values of 2.6 μM (IC50 = 34.0 ± 0.5 μM) and 5.8 μM
(IC50 = 112 ± 1.4 μM) respectively. The compound (7f) alone was found to have high cytotoxicity against Caco-2 cell
lines with IC50 value of 2.3 μM (IC50 = 87 ± 2.6 μM).


Keywords


Anticancer, HeLa, 1, 3, 4-Oxadiazoles, HepG2, cytotoxicity

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The Dhaka University Journal of Pharmaceutical Sciences
ISSN 1816-1820 (Print) 1816-1839 (Online)