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, V.A. Dzhemileva, L.U. Tuktarova, R.A. Makarov, A.A. Islamov, I.I. Mulyukova, A.R. Dzhemilev, U.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 2015

2018-02-27

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.

https://repo.bashgmu.ru/publication/674

https://repo.bashgmu.ru/files/762