56074-98-7

Upstream product

• 54730-30-2 4-hydroxy-3-C-prenylbenzaldehyde 
• 77-78-1 dimethyl sulfate 
• 68-12-2 N,N-dimethyl-formamide 
• 187400-01-7 4-Bromo-1-methoxy-2-(3-methyl-but-2-enyl)-benzene 
• 870-63-3 prenyl bromide 
• 223418-72-2 2-(3-bromo-4-methoxyphenyl)-1,3-dioxolane 
• 106-41-2 4-bromo-phenol 
• 104108-29-4 prenyl tributylstannane 
• 74-88-4 methyl iodide 
• 151071-00-0 4-bromo-2-(3-methylbut-2-en-1-yl)phenol 
• 2973-78-6 3-bromo-4-hydroxybenzylaldehyde 
• 162271-15-0 2-bromo-4-(1,3-dioxolan-2-yl)phenol 

Downstream Products

• 125116-29-2 2'-Hydroxy-4',6'-di-(methoxymethoxy)-4-methoxy-3-(γ,γ-dimethylallyl)chalcone 
• 259867-00-0 (R)-((2S,5R)-5-Isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazin-2-yl)-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-methanol 
• 259866-97-2 (S)-((2S,5R)-5-Isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazin-2-yl)-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-methanol 
• 943860-38-6 C₂₃H₂₆O₅ 
• 943860-42-2 C₂₂H₂₄O₄ 
• 943860-43-3 C₂₁H₂₂O₃ 
• 125116-31-6 5,7-Di-(methoxymethoxy)-4'-methoxy-8,3'-di-(γ,γ-dimethylallyl)flavanone 
• 125116-30-5 2'-Hydroxy-4',6'-di(methoxymethoxy)-4-methoxy-3,3'-di-(γ,γ-dimethylallal)chalcone 
• 125949-03-3 5,7-Dihydroxy-4'-methoxy-8,3'-di-(γ,γ-dimethylallyl)flavanone 
• 259867-08-8 1-[2-(2-{2-{2-[2-(2-benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionylamino}-acetylamino)-3-(1H-indol-3-yl)-propionyl]-pyrrolidine-2-carboxylic acid benzyl ester 
• 259867-09-9 1-[2-(2-{2-{2-[2-(2-benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionylamino}-acetylamino)-3-(1H-indol-3-yl)-propionyl]-pyrrolidine-2-carboxylic acid benzyl ester 
• 259867-07-7 (2S,3R)-2-{2-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionic acid methyl ester 
• 259867-06-6 (2S,3S)-2-{2-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of (±)Abyssinone I and related compounds: Their anti-oxidant and cytotoxic activities

An efficient and facile synthesis of naturally occurring prenylated flavonoids and their analogs have been described. Abyssinone I (9a) was prepared by condensing 2,2-dimethyl chrom-3-en-6-carboxaldehyde (5a) with protected resacetophenone under phase transfer conditions followed by deprotection and cyclization. The influence of prenyl group on anti-oxidant and cytotoxic activities was studied. The presence of 3′-prenyl group as in 8c enhanced radical scavenging activity but decreased reducing power activity when compared to non-prenylated analog 8f. In vitro testing in MCF-7 cell line revealed that prenylated chalcones and flavanones showed better inhibitory activity than their non-prenylated counterparts. Abyssinone I and its chalcone though exhibited negligible anti-oxidant activity their cytotoxic activities were comparable with other prenylated analogs.

CHEMOTHERAPEUTIC FLAVONOIDS, AND SYNTHESES THEREOF

Substituted flavonoid compounds, and pharmaceutical formulations of flavonoid compounds are described. Also described are processes for preparing flavonid compounds, as are methods for treating cancer in mammals using the described flavonoid compounds or pharmaceutical formulations thereof.

Synthesis and biological evaluation of (±)-abyssinone II and its analogues as aromatase inhibitors for chemoprevention of breast cancer

An efficient and economical synthesis of the naturally occurring aromatase inhibitor abyssinone II was performed. The synthesis features an optimized aromatic prenylation reaction in which an arylcopper intermediate is reacted with prenyl bromide to afford a key intermediate that was converted to a prenylated aromatic aldehyde. Condensation of the aldehyde with an o-hydroxyacetophenone under Claisen-Schmidt conditions afforded a chalcone that was deprotected and cyclized in the presence of sodium acetate in refluxing ethanol to afford (±)-abyssinone II. The synthesis proved to be versatile enough to provide an array of abyssinone II derivatives that were evaluated as aromatase inhibitors. Methylation of the 4′-hydroxyl group of (±)-abyssinone II resulted in a significant increase in aromatase inhibitory activity, and further smaller increases in activity resulted from the methylation of the 7-hydroxyl group and removal of the prenyl side chain. As a result of these structural changes, the most active flavanone of the series was 20 times more potent than (±)-abyssinone II (IC50 40.95 μM).

Synthesis of the cyclic heptapeptide Substance P antagonist, dihydro-WIN67689 and determination of the stereochemistry of the modified tyrosine moiety

The total synthesis of semi-synthetic cyclic heptapeptide dihydro-WIN67689, a Substance P antagonist 70 times more potent than the naturally occurring cyclic peptide WIN66306, established the stereochemistry of the β-OH group in the isoprenyltyrosine moiety in I-III as R.

Synthesis of 2,3-dihydro-5,7-dihydroxy-8-(3-methyl-2-butenyl)-2--4H-benzopyran-4-one

Synthesis of the title compound (VI) has been achieved starting from 2'-hydroxy-4',6'-di-(methoxymethoxy)-4-methoxy-3-(γ,γ-dimethylallyl)chalcone (III).Prenylation of III with prenyl bromide in the presence of methanolic KOH affords 2'-hydroxy-4',6'-di-(methoxymethoxy)-4-methoxy-3, 3'-di-(γ,γ-dimethylallyl)chalcone (IV), which on cyclization followed by dimethoxymethylation affords VI.