586410-23-3

Basic information

• Product Name: (Z)-3,4’,5-Trimethoxy-3’-(tert-butyldimethylsilyloxy)stilbene
• Synonyms: (Z)-3,4’,5-Trimethoxy-3’-(tert-butyldimethylsilyloxy)stilbene;[5-[(1Z)-2-(3,5-DiMethoxyphenyl)ethenyl]-2-Methoxyphenoxy](1,1-diMethylethyl)diMethyl-silane;4-[(1Z)-2-(3,5-DiMethoxyphenyl)ethenyl]-2-[[(1,1-diMethylethyl)diMethylsilyl]oxy]-1-Methoxy-benzene
• CAS NO: 586410-23-3
• Molecular Formula: C₂₃H₃₂O₄Si
• Molecular Weight: 400.58328
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 586410-23-3.mol

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Dichloromethane, Methanol
• CAS DataBase Reference: (Z)-3,4’,5-Trimethoxy-3’-(tert-butyldimethylsilyloxy)stilbene(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-3,4’,5-Trimethoxy-3’-(tert-butyldimethylsilyloxy)stilbene(586410-23-3)
• EPA Substance Registry System: (Z)-3,4’,5-Trimethoxy-3’-(tert-butyldimethylsilyloxy)stilbene(586410-23-3)

Safety Data

• Hazardous Substances Data: 586410-23-3(Hazardous Substances Data)

Usage

Uses

Intermediate in the production of anticancer/antitumor stilbene derivatives.

Upstream product

• 24131-30-4 (3,5-dimethoxybenzyl)triphenylphosphonium bromide 
• 97315-18-9 p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde 
• 621-59-0 isovanillin 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 586410-08-4 (Z)-3′-hydroxyl-3,4′,5-trimethoxystilbene 

Relevant articles and documents

Design, synthesis and biological evaluation of novel stilbene-based antitumor agents

A series of novel stilbene derivatives has been synthesized and studied with the main goal to investigate SAR of the amino compound 1a, as well as to improve its water solubility, a potentially negative aspect of the molecule that could be a serious obsta

Synthesis of radiolabeled stilbene derivatives as new potential PET probes for aryl hydrocarbon receptor in cancers

New carbon-11 and fluorine-18 labeled stilbene derivatives, cis-3,5-dimethoxy-4′-[11C]methoxystilbene (4′-[11C]8a), cis-3,4′,5-trimethoxy-3′-[11C]methoxystilbene (3′-[11C]8b), trans-3,5-dimethoxy-4′-[11C]methoxystilbene (4′-[11C]10a), trans-3,4′,5-trimethoxy-3′-[11C]methoxystilbene (3′-[11C]10b), cis-3,5-dimethoxy-4′-[18F]fluorostilbene (4′-[18F]12a), and trans-3,5-dimethoxy-4′-[18F]fluorostilbene (4′-[18F]13a), were designed and synthesized as potential PET probes for aryl hydrocarbon receptor (AhR) in cancers.

Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents

Resveratrol 1 (3,4′,5-trihydroxy-trans-stilbene), a phytoalexin present in grapes and other food products, has recently been suggested as a potential cancer chemopreventive agent based on its striking inhibitory effects on cellular events associated with cancer initiation, promotion, and progression. This triphenolic stilbene has also displayed in vitro growth inhibition in a number of human cancer cell lines. In this context, a series of cis- and trans-stilbene-based resveratrols were prepared with the aim of discovering new lead compounds with clinical potential. All the synthesized compounds were tested in vitro for cell growth inhibition and the ability to induce apoptosis in HL60 promyelocytic leukemia cells. The tested trans-stilbene derivatives were less potent than their corresponding cis isomers, except for trans-resveratrol, whose cis isomer was less active. The best results were obtained with compounds 11b and 7b, the cis-3,5-dimethoxy derivatives of rhapontigenin 10a (3,5,3′-trihydroxy-4′methoxy-transstilbene) and its 3′-amino derivative 10b, respectively, which showed apoptotic activity at nanomolar concentrations. The corresponding trans isomers 12b and 8b were less active both as antiproliferative and as apoptosis-inducing agents. Of interest, 11b and 7b were active toward resistant HL60R cells and their activity was higher than that of several classic chemotherapeutic agents. The flow cytometry assay showed that at 50 nM compounds 7b or 11b were able to recruit almost all cells in the apoptotic sub-G0-G1 peek, thus suggesting that the main mechanism of cytotoxicity of these compounds could be the activation of apoptosis. These data indicate unambiguously that structural alteration of the stilbene motif of resveratrol can be extremely effective in producing potent apoptosis-inducing agents.