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

Synthesis of novel unsymmetrical alkyl-aryl-selenides: β-carbonyl-selenides derivatives and anticancer evaluation

Shuxiao Feng, Kaiyan Qi, Junying Ma, Yafei Guo, Jiayu Gao, Pu Liu, Junling Wang, Guangna Gu, Le Dong, Jinhua Wang, Wan Li, Yihui Yang, Guanhua Du, Lingbo Qu, and Shouren Zhang

College of Chemical Engineering and Pharmaceutical, Henan University of Science and Technology, Luoyang, People’s Republic of China

E-mail: qulingbo@zzu.edu.cn

Received: 16 December 2021  Accepted: 3 March 2022

Abstract:

As a new kind of unsymmetrical alkyl-aryl-selenides, a series of novel β-carbonyl-selenides derivatives were synthesized with high regioselectivity and substrates tolerance. Total six series and forty-four compounds were generated. The in vitro antiproliferative activities were evaluated on U251-MG, U87-MG, MDA-MB-231, HCT116 and SW620 cells lines. Structure and antiproliferative relationship were discussed. Among them, (±)-N, N′-(1,2-phenylene)-bis-(2-((3-oxobutan-2-yl)selanyl) benzamide) (5t) has significant antiproliferative activity and potential value as anticancer agent with IC₅₀ values < 2.63 µM, while the IC₅₀ values of Ebselen > 86.36 µM in test tumor cells.

Keywords: Organoseleniu; Compounds; Alkyl-aryl-selenides; β-carbonyl-selenides; Anticancer activity

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-022-02164-6

Chemical Papers 76 (9) 5471–5485 (2022)