CATALYTIC CYCLOMETALLATION IN STEROID CHEMISTRY III1: SYNTHESIS OF STEROIDAL DERIVATIVES OF 5Z,9Z-DIENOIC ACID AND INVESTIGATION OF ITS HUMAN TOPOISOMERASE I INHIBITORY ACTIVITY

Дьяконов, В.А.; Джемилева, Л.У.; Туктарова, Р.А.; Макаров, А.А.; Исламов, И.И.; Мулюкова, А.Р.; Джемилев, У.М.; D’yakonov, Vladimir A.; Dzhemileva, Lilya U.; Tuktarova, Regina A.; Makarov, Aleksey A.; Islamov, Ilgiz I.; Mulyukova, Alfiya R.; Dzhemilev, Usein M.

CATALYTIC CYCLOMETALLATION IN STEROID CHEMISTRY III1: SYNTHESIS OF STEROIDAL DERIVATIVES OF 5Z,9Z-DIENOIC ACID AND INVESTIGATION OF ITS HUMAN TOPOISOMERASE I INHIBITORY ACTIVITY

D’yakonov, Vladimir A., Dzhemileva, Lilya U., Tuktarova, Regina A., Makarov, Aleksey A., Islamov, Ilgiz I., Mulyukova, Alfiya R., Dzhemilev, Usein M.

Publication date: 2015

Abstract:

Two approaches to stereoselective synthesis of steroid 5Z,9Z-dienoic acids were developed, the first one being based on the cross-cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran and 1,2-diene cholesterol derivatives on treatment with EtMgBr catalyzed by Cp2TiCl2, while the other involving the synthesis of esters of hydroxy steroids with (5Z,9Z)-tetradeca-5,9-dienedioic acid, prepared in two steps using homo-cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran as the key step. High inhibitory activity of the synthesized acids against human topoisomerase I (hTop1) was found.

Keywords:
Cross-cyclomagnesiation 5Z,9Z-dienoic acids, Titanocene dichloride, Grignard reagents, Magnesacyclopentane, Dzhemilev reaction, Topoisomerase I inhibitors

Тип: Article

CATALYTIC CYCLOMETALLATION IN STEROID CHEMISTRY III1: SYNTHESIS OF STEROIDAL DERIVATIVES OF 5Z,9Z-DIENOIC ACID AND INVESTIGATION OF ITS HUMAN TOPOISOMERASE I INHIBITORY ACTIVITY

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