Catalytic cyclometallation in steroid chemistry V: Synthesis of hybrid molecules based on steroid oximes and (5Z,9Z)-tetradeca-5,9-dienedioic acid as potential anticancer agents

Publication date: October 2018Source: Steroids, Volume 138Author(s): Vladimir A. D'yakonov, Regina A. Tuktarova, Lilya U. Dzhemileva, Svetlana R. Ishmukhametova, Milyausha M. Yunusbaeva, Usein M. DzhemilevAbstractSynthetic analogues of natural 5Z,9Z-dienoic acids - hybrid molecules based on the oximes of cholesterol, pregnenolone, and androsterone with 1,14-tetradeca-5Z,9Z-dienedicarboxylic acid - were synthesized for the first time and studied for antitumor activity in vitro. The acid was prepared using catalytic cyclomagnesiation of O-containing 1,2-dienes with Grignard reagent in the presence of Cp2TiCl2 as the key step. Using flow cytometry, it was shown for the first time that the new molecules are efficient apoptosis inducers in the HeLa, Hek293, U937, Jurkat, and K562.Graphical abstract
Source: Steroids - Category: Drugs & Pharmacology Source Type: research