Open AccessAntiproliferative Activity of (−)‐Isopulegol‐based 1,3‐Oxazine, 1,3‐Thiazine and 2,4‐Diaminopyrimidine Derivatives
Author(s) -
Bamou Fatima Z.,
Le Tam M.,
Tayeb Bizhar A.,
Tahaei Seyyed A. S.,
Minorics Renáta,
Zupkó István,
Szakonyi Zsolt
Publication year - 2022
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.202200169
Subject(s) - hela , thiazine , chemistry , moiety , oxazines , pyrimidine , aniline , stereochemistry , trifluoromethyl , bioassay , combinatorial chemistry , cancer cell , in vitro , cancer , biochemistry , medicinal chemistry , organic chemistry , biology , alkyl , genetics
A series of novel heterocyclic structures, namely 1,3‐oxazines, 1,3‐thiazines and 2,4‐diaminopyrimidines, were designed and synthesised. The bioassay tests demonstrated that, among these analogues, 2,4‐diaminopyridine derivatives showed significant antiproliferative activity against different human cancer cell lines (A2780, SiHa, HeLa, MCF‐7 and MDA‐MB‐231). Pyrimidines substituted with N 2 ‐( p ‐trifluoromethyl)aniline, in particular, displayed a potent inhibitory effect on the growth of cancer cells. Structure–activity relationships were also studied from the aspects of stereochemistry on the aminodiol moiety as well as exploring the effects of substituents on the pyrimidine scaffold.