186837-48-9

Upstream product

• 160257-85-2 5-iodo-2-methoxyphenol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 179902-22-8 1-acetoxy-4-iodo-2-methoxy-benzene 
• 183593-98-8 5-iodo-2-methoxyphenyl acetate 

Downstream Products

• 186837-62-7 4-Bromo-3-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-1-triisopropylsilanyl-1H-pyrrole-2-carboxylic acid methyl ester 
• 186837-51-4 4-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-1-triisopropylsilanyl-3-(3,4,5-trimethoxy-phenyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 192809-69-1 1-(tert-butyldimethylsiloxy)-2,3-dimethoxy-6-[3-(tert-butyldimethylsiloxy)-4-(methoxyphenyl)ethynyl]-5-methylbenzene 
• 900152-54-7 methyl 4-bromo-5-{3-[tert-butyl(dimethyl)silyloxy]-4-methoxyphenyl}-1-(4-methoxybenzyl)-1H-pyrrole-2-carboxylate 
• 900152-42-3 4-(3-hydroxy-4-methoxy-phenyl)-1-(4-methoxy-benzyl)-5-(3,4,5-trimethoxy-phenyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 900152-46-7 4-benzo[1,3]dioxol-5-yl-5-(3-hydroxy-4-methoxy-phenyl)-1-(4-methoxy-benzyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 900152-44-5 5-(3-hydroxy-4-methoxy-phenyl)-1-(4-methoxy-benzyl)-4-(3,4,5-trimethoxy-phenyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 192809-55-5 (Z)-1-(3,4-dimethoxy-2-hydroxy-5-methylphenyl)-2-(3-hydroxy-4-methoxyphenyl)ethene 
• 192809-45-3 (Z)-1-(6-acetoxy-5,6-dimethoxy-3-methyl-1-oxocyclohexa-2,4-dien-2-yl)-2-(6-acetoxy-6-methoxy-1-oxocyclohexa-2,4-dien-3-yl)ethene 
• 192809-62-4 (E)-1-(6-acetoxy-5,6-dimethoxy-3-methyl-1-oxocyclohexa-2,4-dien-2-yl)-2-(6-acetoxy-6-methoxy-1-oxocyclohexa-2,4-dien-3-yl)ethene 
• 1067880-35-6 tert-butyl(2-methoxy-5-(1-(3,4,5-trimethoxyphenyl)vinyl)phenoxy)dimethylsilane 
• 1246764-30-6 (5-(2-(2-bromo-3,4,5-trimethoxyphenyl)ethynyl)-2-methoxyphenoxy)(tert-butyl)dimethylsilane 
• 1067880-31-2 isocombretastatin A₄ 
• 1067880-36-7 C₂₀H₂₂O₆ 

Relevant academic research and scientific papers

4,5-Diaryl-1H-pyrrole-2-carboxylates as combretastatin A-4/lamellarin T hybrids: Synthesis and evaluation as anti-mitotic and cytotoxic agents

The 4,5-diarylated-1H-pyrrole-2-carboxylates 3-8 have each been prepared as hybrids of the potent anti-mitotic agent combretastatin A-4 (1) and the similarly active marine alkaloid lamellarin T (2). The key steps involved selective lithium-for-halogen exchange at C5 within the N-PMB protected 4,5-dibromopyrrole 22 and Negishi cross-coupling of the derived zincated species with the relevant aryl iodide. The ensuing 5-aryl-4-bromopyrrole then engaged in Suzuki-Miyaura cross-coupling with the appropriate arylboronic acid to give the 4,5-diarylated pyrroles 4, 6 and 8. TFA-promoted removal of the N-PMB group within these last compounds then gave the N-unsubstituted congeners 3, 5 and 7. Compounds 3-8 have all been evaluated for their anti-mitotic and cytotoxic properties and two of them, 3 and 5, display useful activities although they are less potent than combretastatin A-4. Crown Copyright

New method of synthesis and biological evaluation of some combretastatin A-4 analogues

A series of novel combretastatin A-4 analogues was synthesized in 36-64% yields by Negishi cross-coupling reaction under mild conditions. The prepared compounds exhibit good cytotoxicity against HBL100 epithelial cell lines (IC50=0.022-10.31 ). Georg Thieme Verlag Stuttgart · New York.

Cyclization pathways of a (Z)-stilbene-derived bis(orthoquinone monoketal)

Lead tetraacetate mediated oxidation of a (Z)-bisphenolic stilbene derivative affords a bis(orthoquinone monoketal) product. Thermolysis studies of this highly unsaturated dione reveal that sigmatropic hydrogen shifts, followed by either of two distinct solvolytic ring closures, constitute the predominate reaction pathways under heating. No evidence for a desired 6π electron electrocyclization was forthcoming.