Stereoselective synthesis of 11-phenylundeca-5Z,9Z-dienoic acid and investigation of its human topoisomerase I and II alpha inhibitory activity

Stereoselective synthesis of 11-phenylundeca-5Z,9Z-dienoic acid and investigation of its human topoisomerase I and II alpha inhibitory activity Full article

Journal

Bioorganic and Medicinal Chemistry Letters
ISSN: 0960-894X , E-ISSN: 1464-3405

Output data

Year: 2015, Volume: 25, Number: 11, Pages: 2405-2408 Pages count : DOI: 10.1016/j.bmcl.2015.04.011

Tags

5Z,9Z-Dienoic acids; DNA-binding; Topoisomerase I; Topoisomerase II alpha; Molecular docking

Authors

D'yakonov Vladimir A. ¹ , Dzhemileva Lilya U. ^2,3 , Makarov Aleksey A. ¹ , Mulukova Alfiya R. ¹ , Baev Dmitry S. ⁴ , Khusnutdinova Elza K. ² , Tolstikova Tatiana G. ⁴ , Dzhemilev Usein M. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Inst Petrochem & Catalysis, Ufa 450075, Russia
2	(Данные Web of science) Bashkir State Univ, Dept Genet & Fundamental Med, Ufa 450043, Bashkortostan, Russia
3	(Данные Web of science) Bashkir State Univ, Dept Immunol & Human Reprod Hlth, Ufa 450043, Bashkortostan, Russia
4	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia

(5Z,9Z)-11-Phenylundeca-5,9-dienoic acid was stereoselectively synthesized, based on original cross-cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran and buta-2,3-dien-1-ylbenzene with EtMgBr in the presence of Cp2TiCl2 catalyst giving 2,5-dialkylidenemagnesacyclopentane in 86% yield. The acid hydrolysis of the product and the Jones oxidation of the resulting 2-{[(5Z,9Z)-11-phenylundeca-5,9-dien-1-yl]oxy}tetrahydro-2H-pyran afforded (5Z,9Z)-11-phenylundeca-5,9-dienoic acid in an overall yield of 75%. A high inhibitory activity of the synthesized acid with respect to human topoisomerase I (hTop1) and II (hTop2 alpha) was determined. (C) 2015 Elsevier Ltd. All rights reserved.

D'yakonov V.A. , Dzhemileva L.U. , Makarov A.A. , Mulukova A.R. , Baev D.S. , Khusnutdinova E.K. , Tolstikova T.G. , Dzhemilev U.M.
Stereoselective synthesis of 11-phenylundeca-5Z,9Z-dienoic acid and investigation of its human topoisomerase I and II alpha inhibitory activity
Bioorganic and Medicinal Chemistry Letters. 2015. V.25. N11. P.2405-2408. DOI: 10.1016/j.bmcl.2015.04.011 WOS Scopus РИНЦ

Published print:

Jun 1, 2015

Web of science	WOS:000354115400028
Scopus	2-s2.0-84937759965
Elibrary	23992178
OpenAlex	W2017100580