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Stereoselective synthesis of 11-phenylundeca-5Z,9Z-dienoic acid and investigation of its human topoisomerase I and IIα inhibitory activity.
D'yakonov, Vladimir A; Dzhemileva, Lilya U; Makarov, Aleksey A; Mulukova, Alfiya R; Baev, Dmitry S; Khusnutdinova, Elza K; Tolstikova, Tatiana G; Dzhemilev, Usein M.
Bioorg Med Chem Lett ; 25(11): 2405-8, 2015 Jun 01.
Article in English | MEDLINE | ID: mdl-25913198

ABSTRACT

(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-2Н-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 (hTop2α) was determined.


Subject(s)
DNA Topoisomerases, Type I/metabolism , DNA-Binding Proteins/antagonists & inhibitors , Fatty Acids, Unsaturated/chemical synthesis , Fatty Acids, Unsaturated/pharmacology , Topoisomerase I Inhibitors/chemical synthesis , Topoisomerase I Inhibitors/pharmacology , Antigens, Neoplasm/genetics , Antigens, Neoplasm/metabolism , Computer Simulation , DNA Topoisomerases, Type II/genetics , DNA Topoisomerases, Type II/metabolism , DNA-Binding Proteins/genetics , DNA-Binding Proteins/metabolism , Fatty Acids, Unsaturated/chemistry , Gene Expression Regulation, Enzymologic , Humans , Models, Chemical , Models, Molecular , Molecular Structure , Topoisomerase I Inhibitors/chemistry
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