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Synthesis and Anticancer Properties of Oxazepines Related to Azaisoerianin and IsoCoQuines
Author(s) -
Khelifi Ilhem,
Pecnard Shan,
Bernadat Guillaume,
Big Jérome,
Levaique Hélène,
Dubois Joëlle,
Provot Olivier,
Alami Mouad
Publication year - 2020
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.202000197
Subject(s) - cytotoxicity , k562 cells , chemistry , tubulin , cell cycle , cancer cell lines , a549 cell , cell culture , stereochemistry , cancer , pharmacology , cancer cell , cell , biochemistry , in vitro , biology , microbiology and biotechnology , microtubule , genetics
In this article, we report the synthesis and biological properties of a series of novel oxazepines related to iso CA‐4 having significant antitumor properties. Among them, three oxazepin‐9‐ol derivatives display a nanomolar or a sub‐nanomolar cytotoxicity level against five human cancer cell lines (HCT116, U87, A549, MCF7, and K562). It was demonstrated that the lead compound in this series inhibits tubulin assembly with an IC 50 value of 1 μM and totally arrests the cellular cycle in the G2/M phase at the low concentration of 5 nM in HCT116 and K562 cells. Molecular modeling studies perfectly corroborates these promising results.