97073-44-4

Upstream product

• 82628-68-0 3,4-dihydroxy-5-methylbenzaldehyde 
• 100-44-7 benzyl chloride 
• 32263-14-2 4-hydroxy-3-methoxy-5-methylbenzaldehyde 
• 100-39-0 benzyl bromide 
• 1257415-72-7 3-(benzyloxy)-4-hydroxy-5-methylbenzaldehyde 
• 488-17-5 3-methylbenzene-1,2-diol 

Downstream Products

• 393803-74-2 formic acid 3,4-bis-benzyloxy-5-methyl-phenyl ester 
• 393803-69-5 Acetic acid 6-[1-((1aR,3aS,5S,7aS,7bS)-5-acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-meth-(Z)-ylidene]-4-hydroxy-5-methyl-3-oxo-cyclohexa-1,4-dienyl ester 
• 393803-72-0 3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bS)-7b-[6-acetoxy-3-hydroxy-2-methyl-4-oxo-cyclohexa-2,5-dien-(Z)-ylidenemethyl]-1a,4,4,7a-tetramethyl-decahydro-1-oxa-cyclopropa[a]naphthalen-5-yl ester 
• 393803-50-4 3,4-dibenzyloxy-5-methylphenol 
• 393803-52-6 1,2-dibenzyloxy-5-tert-butyldimethylsilyloxy-3-methylbenzene 
• 393803-57-1 1,2-dibenzyloxy-4-bromo-5-tert-butyldimethylsilyloxy-3-methylbenzene 
• 393803-79-7 Acetic acid (R)-(6-acetoxy-3,4-dihydroxy-2-methyl-phenyl)-((1aR,3aS,5S,7aS,7bR)-5-acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-methyl ester 
• 393803-68-4 Acetic acid (S)-(6-acetoxy-3,4-dihydroxy-2-methyl-phenyl)-((1aR,3aS,5S,7aS,7bR)-5-acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-methyl ester 
• 393803-81-1 3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(R)-acetoxy-(6-acetoxy-3,4-dihydroxy-2-methyl-phenyl)-methyl]-1a,4,4,7a-tetramethyl-decahydro-1-oxa-cyclopropa[a]naphthalen-5-yl ester 
• 393803-71-9 3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(S)-acetoxy-(6-acetoxy-3,4-dihydroxy-2-methyl-phenyl)-methyl]-1a,4,4,7a-tetramethyl-decahydro-1-oxa-cyclopropa[a]naphthalen-5-yl ester 
• 393803-77-5 Acetic acid (R)-(6-acetoxy-3,4-bis-benzyloxy-2-methyl-phenyl)-((1aR,3aS,5S,7aS,7bR)-5-hydroxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-methyl ester 
• 393803-65-1 Acetic acid (S)-(6-acetoxy-3,4-bis-benzyloxy-2-methyl-phenyl)-((1aR,3aS,5S,7aS,7bR)-5-hydroxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-methyl ester 
• 393803-78-6 Acetic acid (R)-(6-acetoxy-3,4-bis-benzyloxy-2-methyl-phenyl)-((1aR,3aS,5S,7aS,7bR)-5-acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-methyl ester 
• 393803-67-3 Acetic acid (S)-(6-acetoxy-3,4-bis-benzyloxy-2-methyl-phenyl)-((1aR,3aS,5S,7aS,7bR)-5-acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-methyl ester 

Relevant academic research and scientific papers

Synthesis of methylated quercetin analogues for enhancement of radical-scavenging activity

Three quercetin derivatives with enhanced radical-scavenging activity were designed and synthesised. Because the radical-scavenging reaction of quercetin is known to proceed via an electron transfer from quercetin to radicals, producing the corresponding quercetin radical cation intermediate, the introduction of electron-donating groups into the quercetin molecule is expected to enhance its radical-scavenging activity. Thus, methyl groups were introduced into the catechol moiety in the quercetin molecule at either the 2′- or 5′-position, or both. All three quercetin analogues were found to exhibit higher radical-scavenging activity than the parent quercetin. The activity of 5′-methylquercetin is the highest among the three analogues. The optimised structure of 5′-methylquercetin calculated by density functional theory demonstrated a coplanar structure between the 4H-curomen (AC rings) and catechol (B ring) moieties, while dimethylquercetin and 2′-methylquercetin have a twisted structure between the AC and B rings. These results demonstrate that the highest radical-scavenging activity of 5′-methylquercetin is due to the stabilisation of the radical cation intermediate by the electron-donating effect of the methyl group as well as by the planar structure of the molecule.

Molecular Mechanism of Action of 5,6-Dihydroxytryptamine. Synthesis and Biological Evaluation of 4-Methyl-, 7-Methyl-, and 4,7-Dimethyl-5,6-dihydroxytryptamines

The major mechanism by which the serotonin neurotoxin 5,6-dihydroxytryptamine (5,6-DHT) expresses its neurodegenerative action may involve alkylation of biological nucleophiles by the electrophilic quinoid autoxidation products.To determine the relative importance of various sites on these autoxidation products toward alkylation we have rationally designed and synthesized 4-Me-5,6-DHT (16a), 7-Me-5,6-DHT (16b), and 4,7-Me2-5,6-DHT (16c).The indole nucleus of these analogues was constructed by the reductive cyclization of the corresponding 2,β-dinitrostyrenes, and the aminoethyl side chain was introduced via gramine methiodides.Redox data showed that all the analogues are more readily oxidized compared to 5,6-DHT.The biological activity was evaluated in differentiated neuroblastoma N-2a cells in culture.The order of inhibitory potency, as determined by measuring the inhibition of incorporation of thymidine into DNA, was 16c >> 16a > 5,6-DHT 16b.The order of affinity (expressed as IC50 values in μM) for serotonergic uptake as determined by measuring their inhibition of -5-HT uptake was 5,6-DHT (4) > 16c (20) > 16a (23) > 16b (52).The results of these studies established that these rationally designed C-methylated analogues of 5,6-DHT are suitable probes for elucidating the molecular mechanism of action of 5,6-DHT.