162705-13-7Relevant articles and documents
Synthesis, crystal structure and cytotoxic properties of nitrocombretastatins (E)- and (Z)-5-(4-methoxy-3-nitrostyryl)-1,2,3-trimethoxybenzene
Gerova, Mariana S.,Encheva, Gergina R.,Nikolova, Rositsa P.,Chanev, Christo D.,Shivachev, Boris L.,Apostolova, Margarita D.,Petrov, Ognyan I.
, p. 105 - 112 (2016)
(Z)-5-(4-Methoxy-3-nitrostyryl)-1,2,3-trimethoxybenzene (2) is the key intermediate for the preparation of several anticancer agents, belonging to the group of aminocombretastatins (AC7739, AVE8062). Synthesis of the title compounds was achieved by a modified Wittig reaction under Boden's conditions using potassium carbonate as a base and 18-crown-6 as a phase transfer catalyst. Both π-diastereoisomers were characterized by single crystal X-ray diffraction analysis, 1H and 13C NMR spectroscopy. (E)-5-(4-Methoxy-3-nitrostyryl)-1,2,3-trimethoxybenzene (1) crystallizes in the orthorhombic space group Pbca (N° 61) with one molecule per asymmetric unit while (Z)-5-(4-methoxy-3-nitrostyryl)-1,2,3-trimethoxybenzene (2) crystallizes in the monoclinic space group P21/c (N° 14) also with one molecule per asymmetric unit. In both compounds no typical hydrogen bonding interactions could be located. The three-dimensional crystal structure is stabilized by C-H···O interactions. The cytotoxicity of synthesized nitrocombretastatins was also evaluated. The Z-stilbene 2 inhibited cell growth with IC50 of 0.15 and 0.11 μM following 72 h treatment in EA.hy926 and MG-63 cell lines.
Compositions and Methods for Treatment of Cancer
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Paragraph 0054, (2020/12/17)
Resistance of randomly dispersed and oxygen-starved lung tumor cells to chemo- and radiotherapy constitutes the vast majority recurrences and death from lung cancer. We use sickle cells derived from humans with sickle cell anemia to target oxygen-deprived
Pt(IV) prodrugs containing microtubule inhibitors displayed potent antitumor activity and ability to overcome cisplatin resistance
Li, Lingxue,Huang, Xiaochao,Huang, Rizhen,Gou, Shaohua,Wang, Zhimei,Wang, Hengshan
, p. 666 - 679 (2018/07/29)
It is well-known that cisplatin exhibited a broad spectrum of anticancer activities against many solid tumors, but its severe toxicity and drug resistance have largely limited wider clinical applications. Various strategies have been tried to discover new Pt (II) drugs with at least equal activity as well as low toxicity compared to cisplatin, but the inherent problem remains unsolved. Here we report that Pt (IV) complexes comprising a CA-4 analogue, as dual-targeting Pt (IV) prodrug, were synthesized and evaluated for anti-proliferative activity using MTT assay. Among them, complex 19 displayed most potent activity against the tested cancer cell lines, and simultaneously exhibited better cell selectivity between cancer cells and normal cells than that of cisplatin. Mechanism studies revealed that complex 19 effectively induced cell cycle arrest at the G2/M phase and dramatically disrupted the microtubule organization. Moreover, complex 19 significantly induced cell apoptosis and decreased MMP. Importantly, complex 19 significantly inhibited tumor growth in SK-OV-3 xenograft model in vivo without apparent toxicity.
