1415089-15-4

Basic information

• Product Name: (Z)-2-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-1H-indole
• Synonyms: (Z)-2-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-1H-indole
• CAS NO: 1415089-15-4
• Molecular Weight: 309.365
• Mol File: 1415089-15-4.mol

Chemical Properties

• CAS DataBase Reference: (Z)-2-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-1H-indole(1415089-15-4)
• EPA Substance Registry System: (Z)-2-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-1H-indole(1415089-15-4)

Safety Data

• Hazardous Substances Data: 1415089-15-4(Hazardous Substances Data)

Upstream product

• 26340-49-8 2-iodo-1H-indole 
• 53560-33-1 3,4,5-trimethoxyphenylacetylene 
• 53560-32-0 3,4,5-trimethoxy-β-bromostyrene 
• 234123-50-3 5-[(Z)-2-Bromoethenyl]-1,2,3-trimethoxybenzene 
• 1415089-11-0 (Z)-2-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-indole-1-carboxylic acid tert-butyl ester 
• 1415089-17-6 2-((3,4,5-trimethoxyphenyl)ethynyl)-1H-indole 

Relevant articles and documents

Synthesis of (Z) isomers of benzoheterocyclic derivatives of combretastatin A-4: A comparative study of several methods

Several methods for the preparation of (Z) trimethoxystyrene derivatives 1 were investigated. After finding that the Wittig reaction led to unsatisfactory results, three different strategies were considered: a Suzuki coupling with a stereodefined monobromoalkene, a combination of hydrosilylation/vinylsilane hydrolysis and a palladium-catalyzed semi-hydrogenation step, using DMF/KOH as the hydrogen source. Our studies led us to prepare a series of diarylacetylene derivatives via a Sonogashira coupling reaction, and also to find out a copper-free basic cyclization leading to benzo[b]thiophenes. The final choice for the synthesis method of 1 strongly depends on the target compound but the semi-hydrogenation, which avoids the use of a toxic tin reducing agent, should be generally preferred.

Synthesis and biological evaluation of novel heterocyclic derivatives of combretastatin A-4

A novel series of combretastatin A-4 heterocyclic analogues was prepared by replacement of the B ring with indole, benzofurane or benzothiophene, attached at the C2 position. These compounds were evaluated for their abilities to inhibit tubulin assembly: derivative cis 3b, having a benzothiophene, showed an activity similar to those of colchicine or deoxypodophyllotoxine. The antiproliferative and antimitotic properties of cis 3b against keratinocyte cancer cell lines were also evaluated and the intracellular organization of microtubules in the cells after treatment with both stereoisomers of 3b was also determined, using confocal microscopy.