ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis and anticancer activity of new azo compounds containing extended π-conjugated systems

Esmail Rezaei-Seresht, Erfan Mireskandari, Mitra Kheirabadi, Hamid Cheshomi, Hasan Rezaei-Seresht, and Leila Sadat Aldaghi

Department of Chemistry, School of Sciences, Hakim Sabzevari University, Sabzevar, Iran

E-mail: e.rezaei@hsu.ac.ir

Abstract: A series of novel azo compounds with extended π-conjugated systems were prepared by azo coupling reaction compounds trans-2-(4′-aminostyryl)-thiophene, 1-(4-aminophenyl)-4-phenyl-1,3-butadiene and 4-amino-4′-methoxystilbene with some phenols. The compounds were evaluated for their cytotoxicity against breast cancer adenocarcinoma (MCF-7), cervix adenocarcinoma (HeLa) and human embryonic kidney (HEK 293) cell lines using the MTT assay. The results showed all derivatives had more toxic effects than tamoxifen. Of all the compounds tested, the azo product obtained from coupling trans-2-(4′-Aminostyryl)-thiophene with 2-naphthol (compound 5b) exhibited the potent in vitro antiproliferative activity with IC₅₀ 27 ± 1 and 18 ± 0 µg/mL against MCF-7 and HeLa cell lines, respectively, while it was devoid of any cytotoxicity against normal HEK 293 cells even at 200 µg/mL.

Keywords: Breast cancer MCF-7; Anticancer activity; Synthesis; Azo compounds

Full paper is available at www.springerlink.com.

DOI: s11696-017-0140-9

Chemical Papers 71 (8) 1463–1469 (2017)