Synthesis and biological evaluation of 4-amino-5-cinnamoylthiazoles as chalcone-like anticancer agents

• Published in: European journal of medicinal chemistry 2018-02, Vol.145, p.404-412
• Main Authors: Ayati, Adileh, Esmaeili, Rezvan, Moghimi, Setareh, Oghabi Bakhshaiesh, Tayebeh, Eslami-S, Zahra, Majidzadeh-A, Keivan, Safavi, Maliheh, Emami, Saeed, Foroumadi, Alireza
• Format: Article
• Language: English
• Subjects: Anticancer; Apoptosis; Chalcone; Cytotoxic activity; Thiazole
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2018.01.015

A series of 4-amino-5-cinnamoylthiazoles 3a-p were designed and synthesized as chalcone-like anticancer agents. The synthesized derivatives 3a-p were evaluated for their in vitro antiproliferative activities against three different human cancer cell lines including MCF-7, HepG2 and SW480. Most of compounds could significantly prevent proliferation of tested cell lines. In particular, the pyrrolidine derivative 3e namely (E)-1-(4-amino-2-(pyrrolidin-1-yl)thiazol-5-yl)-3-(2,4-dichlorophenyl)prop-2-en-1-one showed promising activity, especially against HepG2 cells (IC50 = 10.6 μg/ml). Flow cytometric analyses revealed that the prototype compound 3e can prevent the proliferation of HepG2 cells by blockade of the cell cycle at the G2 phase and induction of apoptosis. [Display omitted] •4-Amino-5-cinnamoylthiazoles were synthesized as chalcone-like anticancer agents.•Target compounds 3a-p were tested against MCF-7, HepG2 and SW400 cell lines.•The pyrrolidine derivative 3e with IC50s = 10.6–18.4 μg/ml showed promising activity.•Compound 3e can induce apoptosis and cause cell cycle arrest at the G2 phase.