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

Synthesis, antiproliferative evaluation, and structure–activity relationships of novel triazole–isoindoline hybrids bearing 3,4,5-trimethoxyphenyl moiety

Qiu Li, Peng Chen, Haikui Yang, Miaolan Luo, Wenwei You, and Peiliang Zhao

Southern Medical University, Guangzhou, People’s Republic of China

E-mail: youww@smu.edu.cn

Abstract: As an aspect of our ongoing research on developing novel antiproliferative agents, 31 new triazole–isoindoline hybrids bearing 3,4,5-trimethoxyphenyl moiety were synthesized and evaluated for their antiproliferative activity against four cancer cell lines (HepG2, HeLa, PC-3, and HCT116). Some compounds showed excellent potency, and compared to fluorouracil, the most promising compound 6s exhibited 5.8-, 4.3-, and 1.3- fold increase in activities against HeLa, HepG2, and PC-3 cell lines with IC₅₀ values of 9.7, 10.7, and 16.8 μM, respectively. Moreover, structure–activity relationship studies indicated that a much shorter amide linkage and electron-withdrawing groups at phenyl ring of the acetamide fragment contribute to the antitumour activity.

Keywords: Isoindoline-1,3-dione ; 1,2,4-Triazole derivatives ; Synthesis ; Antiproliferative activity 

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-017-0311-8

Chemical Papers 72 (3) 651–659 (2018)