102673-80-3

Upstream product

• 55742-65-9 2',5'-dihydroxy-3',4',6'-trimethoxyacetophenone 
• 41222-60-0 3-benzyloxy-4-methoxybenzoyl chloride 
• 1221398-17-9 6,8-dibromo-3,7-O-dimethyltamarixetin 
• 124-41-4 sodium methylate 
• 68-12-2 N,N-dimethyl-formamide 
• 173217-97-5 2-(3-Benzyloxy-4-methoxy-phenyl)-3-hydroxy-5,7,8-trimethoxy-6-methoxymethoxy-chromen-4-one 
• 173217-93-1 2-(3-Benzyloxy-4-methoxy-phenyl)-3,5,6,7,8-pentamethoxy-chromen-4-one 
• 173217-95-3 2-(3-Benzyloxy-4-methoxy-phenyl)-3,6-dihydroxy-5,7,8-trimethoxy-chromen-4-one 
• 173217-96-4 2-(3-Benzyloxy-4-methoxy-phenyl)-6-hydroxy-5,7,8-trimethoxy-chromen-4-one 
• 173217-34-0 1-(2-Hydroxy-3,4,6-trimethoxy-5-methoxymethoxy-phenyl)-ethanone 
• 173217-94-2 2-(3-Benzyloxy-4-methoxy-phenyl)-5-hydroxy-3,6,7,8-tetramethoxy-chromen-4-one 

Downstream Products

• 1178-24-1 3,3',4',5,6,7,8-heptamethoxyflavone 

Relevant academic research and scientific papers

Semisynthesis of natural flavones inhibiting tubulin polymerization, from hesperidin

Semisynthesis of 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxyflavone (1), a natural flavone that binds with high affinity to tubulin, was performed from hesperidin, the very abundant Citrus flavanone, by a five-step sequence. The last step of the synthesis also gave rise to 5,3'-dihydroxy-3,6,7,4'- tetramethoxyflavone (= casticin or vitexicarpin) (10), 5,3'-dihydroxy-3,7,8,4'- tetramethoxyflavone (= gossypetin 3,7,8,4'-tetramethyl ether) (11), and, unexpectedly, 5,7,3'-trihydroxy-3,6,8,4'-tetramethoxyflavone (12) and 5,3'-dihydroxy-8-dimethylamino-3,6,7,4'-tetramethoxyflavone (= 8-dimethylaminocasticin) (13). Cytotoxicity and antitubulin activity of these five flavones, as well as 5,3'-dihydroxy-3,7,4'-trimethoxyflavone (= ayanin) (14) and intermediate 6,8-dibromo-ayanin (8), were evaluated. Comparison of the responses confirmed and clarified the influence of the A-ring substitution pattern on the biological activity.

Studies of the selective O-alkylation and dealkylation of flavonoids. XIX. A convenient method for synthesizing 3,5,6,7,8-pentaoxygenated flavones

The methoxymethyl ethers of 6-hydroxy-5,7,8-trimethoxyflavones, which were derived from 2',5'dihydroxy-3',4',6'-trimethoxyacetophenone, were oxidized with dimethyldioxirane to give the corresponding 3-hydroxyflavones. Selective O-alkylation and dealkylation of the 3-hydroxyflavones were examined and a convenient method for synthesizing the following ten kinds of 3,5,6,7,8- pentaoxygenated flavones was established: 3-hydroxy-5,6,7,8- tetramethoxyflavones, 3,5-dihydroxy-6,7,8-trimethoxyflavones, 3,6-dihydroxy- 5,7,8-trimethoxyflavones, 3,5,6-trihydroxy-7,8-dimethoxyflavones, 3,5,6,7- tetrahydroxy-8-methoxyflavones, and their 3-methyl ethers. Furthermore, 3,5,8-trihydroxy-4',6,7-trimethoxyflavone, 3,8-dihydroxy-4',5,6,7- tetramethoxyflavone, and 5,8-dihydroxy-3,6,7-trimethoxyflavones were similarly synthesized and their spectral properties were examined. Additionally, the proposed structures of three natural flavones were revised.