1462267-57-7

Basic information

• Product Name: (Z)-1-(3-methoxy-2-methylthiophenyl)-2-(3,4,5-trimethoxyphenyl)ethene
• Synonyms: (Z)-1-(3-methoxy-2-methylthiophenyl)-2-(3,4,5-trimethoxyphenyl)ethene
• CAS NO: 1462267-57-7
• Molecular Weight: 346.447
• Mol File: 1462267-57-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-1-(3-methoxy-2-methylthiophenyl)-2-(3,4,5-trimethoxyphenyl)ethene(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-1-(3-methoxy-2-methylthiophenyl)-2-(3,4,5-trimethoxyphenyl)ethene(1462267-57-7)
• EPA Substance Registry System: (Z)-1-(3-methoxy-2-methylthiophenyl)-2-(3,4,5-trimethoxyphenyl)ethene(1462267-57-7)

Safety Data

• Hazardous Substances Data: 1462267-57-7(Hazardous Substances Data)

Upstream product

• 1462267-54-4 (E)-3-(3-methoxy-2-methylthiophenyl)-2-(3,4,5-trimethoxyphenyl)prop-2-enoic acid 
• 88791-05-3 2-mercapto-3-methoxybenzaldehyde 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 951-82-6 3,4,5-trimethoxyphenyl acetic acid 
• 88791-04-2 S-(2-formyl-6-methoxyphenyl)-N,N-dimethylthiocarbamate 
• 88791-03-1 O-(2-formyl-6-methoxyphenyl)-N,N-dimethylthiocarbamate 

Relevant articles and documents

Design, synthesis, and biological evaluation of novel combretastatin A-4 thio derivatives as microtubule targeting agents

A series of novel combretastatin A-4 (CA-4) thio derivatives containing different molecular cores, namely α-phenylcinnamic acids (core 1), (Z)-stilbenes (core 2), 4,5-disubstituted oxazoles (core 3), and 4,5-disubstituted N-methylimidazoles (core 4), as cis-restricted analogues were designed and synthesized. They were selected with the use of a parallel virtual screening protocol including the generation of a virtual combinatorial library based on an elaborated synthesis protocol of CA-4 analogues. The selected compounds were evaluated for antiproliferative activity against a panel of six human cancer cell lines (A431, HeLa, MCF7, MDA-MB-231, A549 and SKOV) and two human non-cancer cell lines (HaCaT and CCD39Lu). Moreover, the effect of the test compounds on the inhibition of tubulin polymerization in vitro was estimated. In the series studied here, oxazole-bridged analogues exhibited the most potent antiproliferative activity. Compounds 23a, 23e, and 23i efficiently inhibited tubulin polymerization with IC50 values of 0.86, 1.05, and 0.85 μM, respectively. Thio derivative 23i, when compared to its oxygen analogue 23j, showed a 5-fold higher inhibitory impact on tubulin polymerization. Compounds 23e and 23i, which showed both best cytotoxic and antitubulin activity, were further studied in terms of their effect on cell cycle distribution and proapoptotic activity. Compound 23e induced a statistically significant block of the cell cycle at the G2/M phase in A431, HaCaT, HeLa, MCF-7, MDA-MB-231, and SKOV-3 cells to an extent comparable to that observed in CA-4. In HeLa and SKOV-3 cells incubated with 23i, a concentration-dependent block of the G2/M phase was observed. The proapoptotic effect of 23e and 23i in A431, HaCaT, MCF-7, MDA-MB-231, and SKOV-3 was demonstrated with ELISA assay and double staining with Annexin V-FITC/PI. The results indicated that compound 23e and 23i may serve as novel lead compounds in research on more effective anticancer agents.