192710-87-5

Upstream product

• 1530-38-7 ((4-methoxyphenyl)methyl)triphenylphosphonium bromide 
• 187803-40-3 3,5-bis(tert-butyldimethylsilyloxy)benzaldehyde 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 103929-84-6 [3,5-di(tert-butyldimethylsilanyloxy)phenyl]methanol 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 3462-97-3 (4-methoxybenzyl)triphenylphosphonium bromide 
• 1145-93-3 diethyl 4-methoxybenzylphosphonate 
• 103929-83-5 methyl 3,5-bis(tert-butyldimethylsilyloxy)benzoate 
• 26153-38-8 3,5-dihydroxybenzaldehyde 
• 192710-88-6 (Z)-3,5-di-(tert-butyldimethylsilyloxy)-4'-methoxystilbene 
• 105-13-5 4-Methoxybenzyl alcohol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 2746-25-0 p-Methoxybenzyl bromide 

Downstream Products

• 1428522-15-9 C₂₉H₂₀N₂O₉ 
• 65728-21-4 5-[(E)-2-(4-methoxyphenyl)vinyl]benzene-1,3-diol 

Relevant academic research and scientific papers

Unexpected O-alkylation and ester migration in phenolic 2,3-diaryl-2,3-dihydrobenzo[b]furans

O-alkylation of 2-(4-methoxyphenyl)-5-hydroxy-3-[1,3-phenylene-bis(4- nitrobenzoate)]-2,3-dihydrobenzo[b]furan results in the unexpected hydrolysis of the nitrobenzoate esters, transfer of a 4-nitrobenzoic acid group to the 5-hydroxyl group and double alkylation of the newly formed 3,5-diphenol moiety. A range of alkyl halides can be used and give access to O-alkyl analogues of -viniferin.

PREVENTION AND TREATMENT OF COLON CANCER

Stilbene compounds for the prevention and treatment of colon cancer or colon inflammation and methods of using same are provided.

Quinone reductase induction activity of methoxylated analogues of resveratrol

Agents that induce the activity of phase II enzymes play an important role in intervening with the carcinogenic process at the initiation stage. Resveratrol is well known for its chemopreventive activity against major stages of carcinogenesis. In this study, several methoxylated analogues of resveratrol were synthesized and evaluated for their ability to induce the activity of the phase II enzyme quinone reductase (QR). Methoxy groups serve to increase lipophilicity and improve metabolic stability. Compared to resveratrol, analogues with ortho-methoxy substituents were found to be more potent inducers of QR and to exert their activity in a qualitatively different manner. The greater induction activities associated with these stilbenoids serve as a useful starting point for the design of improved chemopreventive agents.

Antineoplastic agents. 465. Structural modification of resveratrol: Sodium resverastatin phosphate

As an extension of structure/activity investigations of resveratrol (1), phenstatin (2c), and the cancer antiangiogenesis drug sodium combretastatin A-4 phosphate (2b), syntheses of certain related stilbenes (14) and benzophenones (16) were undertaken. The trimethyl ether derivative of (Z)-resveratrol (4a) exhibited the strongest activity (GI50 = 0.01-0.001 μg/mL) against a minipanel of human cancer cell lines. A monodemethylated derivative (14c) was converted to prodrug 14n (sodium resverastatin phosphate) for further biological evaluation. The antitubulin and antimicrobial activities of selected compounds were also evaluated.