(5Z,9Z)-14-[(3,28-Dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic Acid with Cytotoxic Activity

(5Z,9Z)-14-[(3,28-Dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic Acid with Cytotoxic Activity

For the first time, a synthetic analogue of natural (5Z,9Z)-dienoic acid has been synthesized in the form of a hybrid molecule containing a fragment of oleanolic acid and (5Z,9Z)-tetradeca-5.9-dienedicarboxylic acid, synthesized using a new reaction of Ti-catalyzed homo-cyclomagnesiation 1,2-dienes....

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Bibliographic Details
Published in:MolBank Vol. 2024; no. 1; p. M1758
Main Authors: Tuktarova, Regina A., Dzhemileva, Lilya U., Dzhemilev, Usein M.
Format: Journal Article
Language:English
Published: Basel MDPI AG 01-03-2024
Subjects:
(5Z,9Z)-dienoic acid
Acids
Apoptosis
Cancer
Cell cycle
cytotoxic activity
Cytotoxicity
Dienes
hybrid molecules
oleanolic acid
Oxidation
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Summary:For the first time, a synthetic analogue of natural (5Z,9Z)-dienoic acid has been synthesized in the form of a hybrid molecule containing a fragment of oleanolic acid and (5Z,9Z)-tetradeca-5.9-dienedicarboxylic acid, synthesized using a new reaction of Ti-catalyzed homo-cyclomagnesiation 1,2-dienes. The high cytotoxic activity of (5Z,9Z)-14-[(3,28-dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic acid against tumor cells Jurkat, K562, U937 and HL60 was established. This compound is also an inducer of apoptosis, affects the cell cycle and inhibits human topoisomerase I.
ISSN:1422-8599
1422-8599
DOI:10.3390/M1758