Tuktarova Regina A, Dzhemileva Lilya U, Dzhemilev Usein M, D'yakonov Vladimir A
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow 119991, Russia.
Chemical Engineering Center, ITMO University, Kronverksky Prospekt 49, Saint Petersburg 191002, Russia.
Cancers (Basel). 2024 Nov 21;16(23):3893. doi: 10.3390/cancers16233893.
: A series of synthetic analogs of natural (5Z,9Z)-diene acids were synthesized for the first time in the form of hybrid molecules containing an oleanolic acid fragment. This fragment was simultaneously linked by an amide bond to various hetero- and carbocyclic amines and a complex ester bond to (5Z,9Z)-tetradeca-5,9-dienecarboxylic acid, which was synthesized by a new reaction of Ti-catalyzed homocyclomagnification of 1,2-dienes. : Among the synthesized hybrids, the highest cytotoxic activity was observed for compound in the series of Jurkat, K562, U937, and HEK293, with IC50 values of 4.5; 3.1; 2.8; and 26.17 μM/L, respectively. Furthermore, the synthesized compound has been observed to induce apoptosis and exhibit genotoxicity in Jurkat culture, which suggests that it may be a promising candidate for further investigation as an antitumor agent.
首次合成了一系列天然（5Z，9Z）-二烯酸的合成类似物，其为含有齐墩果酸片段的杂化分子形式。该片段同时通过酰胺键与各种杂环和碳环胺相连，并通过复杂的酯键与（5Z，9Z）-十四碳-5，9-二烯酸相连，（5Z，9Z）-十四碳-5，9-二烯酸是通过1，2-二烯的钛催化同环放大新反应合成的。：在合成的杂化物中，在Jurkat、K562、U937和HEK293系列中观察到化合物的细胞毒性活性最高，IC50值分别为4.5；3.1；2.8；和26.17μM/L。此外，已观察到合成的化合物在Jurkat培养物中诱导凋亡并表现出遗传毒性，这表明它可能是作为抗肿瘤剂进行进一步研究的有希望的候选物。
