166021-12-1

Basic information

• Product Name: methyl (E)-3-<2-(3,4-dimethoxyphenyl)-7-methoxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl>prop-2-enoate
• CAS NO: 166021-12-1
• Molecular Weight: 428.439
• Mol File: 166021-12-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl (E)-3-<2-(3,4-dimethoxyphenyl)-7-methoxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl>prop-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (E)-3-<2-(3,4-dimethoxyphenyl)-7-methoxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl>prop-2-enoate(166021-12-1)
• EPA Substance Registry System: methyl (E)-3-<2-(3,4-dimethoxyphenyl)-7-methoxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl>prop-2-enoate(166021-12-1)

Safety Data

• Hazardous Substances Data: 166021-12-1(Hazardous Substances Data)

Upstream product

• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 2309-07-1 Methyl ferulate 
• 186581-53-3 diazomethane 
• 118799-80-7 (E)-methyl 3-<(2RS,3SR)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methoxycarbonyl-1-benzofuran-5-yl>-1-propenoate 
• 74-88-4 methyl iodide 

Relevant articles and documents

Antiangiogenic activity of synthetic dihydrobenzofuran lignans

A series of synthetic dihydrobenzofuran lignans, obtained by biomimetic oxidative dimerization of caffeic or ferulic acid methyl ester followed by derivatization reactions, was tested for its antiangiogenic activity in the CAM (chorioallantoic membrane) a

Synthesis and biological evaluation of dihydrobenzofuran lignans and related compounds as potential antitumor agents that inhibit tubulin polymerization

A series of 19 related dihydrobenzofuran lignans and benzofurans was obtained by a biomimetic reaction sequence involving oxidative dimerization of p-coumaric, caffeic, or ferulic acid methyl esters, followed by derivatization reactions. All compounds were evaluated for potential anticancer activity in an in vitro human disease-oriented tumor cell line screening panel that consisted of 60 human tumor cell lines arranged in nine subpanels, representing diverse histologies. Leukemia and breast cancer cell lines were relatively more sensitive to these agents than were the other cell lines. Compounds 2c and 2d, but especially 2b (methyl (E)-3-[2-(3,4-dihydroxyphenyl)-7-hydroxy-3- methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate), the dimerization product of caffeic acid methyl ester, containing a 3',4'-dihydroxyphenyl moiety and a hydroxyl group in position 7 of the dihydrobenzofuran ring, showed promising activity. The average GI50 value (the molar drug concentration required for 50% growth inhibition) of 2b was 0.3 μM. Against three breast cancer cell lines, 2b had a GI50 value of 3-side chain, reduction of the methoxycarbonyl functionalities to primary alcohols, or oxidation of the dihydrobenzofuran ring to a benzofuran system resulted in a decrease or loss of cytotoxic activity. Compound 2b inhibited mitosis at micromolar concentrations in cell culture through a relatively weak interaction at the colchicine binding site of tubulin. In vitro it inhibited tubulin polymerization by 50% at a concentration of 13 ± 1 μM. The 2R,3R-enantiomer of 2b was twice as active as the racemic mixture, while the 2S,3S- enantiomer had minimal activity as an inhibitor of tubulin polymerization. These dihydrobenzofuran lignans (2-phenyl- dihydrobenzofuran derivatives) constitute a new group of antimitotic and potential antitumor agents that inhibit tubulin polymerization.