290347-62-5

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 159263-87-3 2-acetyloxy-3-methoxy-6-bromobenzaldehyde 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 7150-01-8 2-acetoxy-3-methoxybenzaldehyde 
• 20035-41-0 6-bromo-2-hydroxy-3-methoxybenzaldehyde 
• 37942-01-1 5-bromo-2-methoxyphenol 
• 61559-82-8 1-Bromo-2,3dihydroxy-4methoxy-benzene 
• 107-30-2 chloromethyl methyl ether 

Downstream Products

• 290347-54-5 2',3'-bis(methoxymethyloxy)-3,4,4',5-tetramethoxydiphenylcarbinol 
• 444992-83-0 1-methoxy-2,3-bis(methoxymethoxy)-4-((3,4,5-trimethoxyphenyl)-ethynyl)benzene 
• 878293-50-6 1-iodo-4-methoxy-2,3-bis(methoxymethoxy)benzene 
• 1355330-13-0 3-methoxy-6-(5-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazol-1-yl)benzene-1,2-diol 
• 1355330-32-3 1-(4-methoxy-2,3-bis(methoxymethoxy)phenyl)-5-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazole 
• 1355330-27-6 1-azido-4-methoxy-2,3-bis(methoxymethoxy)benzene 
• 290347-55-6 phosphoric acid dibenzyl ester 2-(bis-benzyloxy-phosphoryloxy)-6-methoxy-3-(3,4,5-trimethoxy-benzoyl)-phenyl ester 
• 290347-63-6 2',3'-Bis(methoxymethyloxy)-3,4,4',5-tetramethoxybenzophenone 
• 290347-52-3 (2',3'-dihydroxy-4'-methoxyphenyl)(3,4,5-trimethoxyphenyl)methanone 
• 444992-84-1 C₂₂H₃₀O₈ 
• 444992-85-2 C₂₂H₂₈O₈ 
• 109971-64-4 Combretastatin B₁ 
• 109971-63-3 (Z)-3-methoxy-6-(3,4,5-trimethoxystyryl)benzene-1,2-diol 

Relevant academic research and scientific papers

Synthesis of combretastatins A-1 and B-1

Combretastatins A-1 and B-1 have been synthesized by coupling MOM-protected p-iodomethoxycatechol with 3,4,5-trimethoxyphenylacetylene in a Sonogashira reaction.

Hydroxyphenstatin and the prodrugs thereof

The benzophenone derivative of combretastatin A-1, designated “hydroxyphenstatin”, was synthesized by compiling a protected bromobenzene and a benzaldehyde to form a benzhydrol which was subsequently oxidized to the ketone. Hydroxyphenstatin was converted

Direct biooxidation of arenes to corresponding catechols with E. coli JM109 (pDTG602). Application to synthesis of combretastatins A-1 and B-1

Convergent syntheses of combretastatins A-1 and B-1 were accomplished via coupling of biocatalytically generated p-bromomethoxycatechol with trimethoxyphenylacetylene.

Antineoplastic agents. 443. Synthesis of the cancer cell growth inhibitor hydroxyphenstatin and its sodium diphosphate prodrug

A structure - activity relationship (SAR) study of the South African willow tree (Combretum caffrum) antineoplastic constituent combretastatin A-4 (3b) led to the discovery of a potent cancer cell growth inhibitor designated phenstatin (5a). This benzophenone derivative of combretastatin A-4 showed remarkable antineoplastic activity, and the benzophenone derivative of combretastatin A-1 was therefore synthesized. The benzophenone, designated hydroxyphenstatin (6a), was synthesized by coupling of a protected bromobenzene and a benzaldehyde to give the benzhydrol with subsequent oxidation to the ketone. Hydroxyphenstatin was converted to the sodium phosphate prodrug (6e) by a dibenzyl phosphite phosphorylation and subsequent benzyl cleavage (6a → 6d → 6e). While hydroxyphenstatin (6a) was a potent inhibitor of tubulin polymerization with activity comparable to that of combretastatin A-1 (3a), the phosphorylated derivative (6e) was inactive.