Acta Pharm. 70 (2020) 499-513

 

full paper

Original research paper

 

Synthesis and biological evaluation of novel 1,3,4-thiadiazole derivatives as possible anticancer agents

ULVIYE ACAR ÇEVIK, DERYA OSMANIYE, SERKAN LEVENT, BEGÜM NURPELIN SAĞLIK,BETÜL KAYA ÇAVUŞOĞLU, ABDULLAH BURAK KARADUMAN, YUSUF ÖZKAY and ZAFER ASIM KAPLANCIKLI

uacar@anadolu.edu.tr

1 Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, 26470 Eskişehir, Turkey

2 Doping and Narcotic Compounds Analysis Laboratory, Faculty of Pharmacy, Anadolu University, 26470 Eskişehir, Turkey

3 Department of Pharmaceutical Toxicology, Faculty of Pharmacy, Anadolu University, 26470 Eskişehir, Turkey

Accepted November 19, 2019

Published online December 16, 2019

 

The synthesis of new N-(5-substituted-1,3,4-thiadiazol-2-yl)-2-[(5-(substituted amino)-1,3,4-thiadiazol-2-yl)thio]acetamide derivatives and investigation of their anticancer activities were the aims of this work. All the new compounds’ structures were elucidated by elemental analyses, IR, 1H NMR, 13C NMR and MS spectral data. Anticancer activity studies of the compounds were evaluated against MCF-7 and A549 tumor cell lines. In addition, with the purpose of determining the selectivity of cytotoxic activities, the most active compound was screened against a healthy NIH3T3 cell line (mouse embryonic fibroblast cells). Among the tested compounds, compound 4y (N-(5-ethyl-1,3,4-thiadiazol-2-yl)-2-((5-(p-tolylamino)-1,3,4-thiadiazol-2-yl)thio)acetamide), showed promising cytotoxic activity against MCF7 cancer cell with an IC50 value of 0.084 ± 0.020 mmol L–1 and against A549 cancer cell with IC50 value of 0.034 ± 0.008 mmol L–1, compared with cisplatin. The aromatase inhibitory activity was evaluated for compound 4y on MCF-7 cell line showing promising activity with IC50 of 0.062 ± 0.004 mmol L–1.

 

Keywords: 1,3,4-thiadiazole, anticancer activity, aromatase inhibitory activity, MTT assay