99053-61-9

Upstream product

• 28026-96-2 3,5-dihydroxy-4-methylbenzoic acid 
• 100-39-0 benzyl bromide 
• 75238-29-8 3,5-dihydroxy-4-methylbenzoic acid methyl ester 
• 34696-31-6 methyl 3,5-bis(benzyloxy)-4-methylbenzoate 
• 76447-15-9 Benzyl 3,5-Bis(benzyloxy)-4-methylbenzoate 
• 99053-60-8 (3,5-bis(benzyloxy)-4-methylphenyl)methanol 

Downstream Products

• 99053-68-6 3,5-bis(benzyloxy)-4-methyl-β-nitrostyrene 
• 99053-79-9 (5,7-Bis-benzyloxy-6-methyl-1H-indol-3-ylmethyl)-trimethyl-ammonium; iodide 
• 99053-71-1 3,5-bis(benzyloxy)-4-methyl-6,β-dinitrostyrene 
• 99053-82-4 5,7-bis(benzyloxy)-3-(cyanomethyl)-6-methylindole 
• 99053-76-6 (5,7-Bis-benzyloxy-6-methyl-1H-indol-3-ylmethyl)-dimethyl-amine 
• 99053-85-7 2-(5,7-Bis-benzyloxy-6-methyl-1H-indol-3-yl)-ethylamine 
• 99053-74-4 5,7-bis(benzyloxy)-6-methylindole 

Relevant academic research and scientific papers

Preparation of tricyclic analog as CDE ring model of renieramycin marine natural product by novel photo-induced transformation of 6-methoxy-1,2,3,4-tetrahydroisoquinoline-5,8-dione

2-Acetyl-6-[(benzyloxy)methyl]-9-methoxy-8-methyl-11,11adihydro-2H-pyrazino[1,2-b]isoquinoline-1,4,7,10(3H,6H)-tetraone (11a) was prepared as the CDE ring model of renieramycins, and its novel photo-induced transformation was demonstrated to construct a 1,3-dioxol ring.

Mechanism and Products of Autoxidation of 5,7-Dihydroxytryptamine

The neurodegenerative effect of 5,7-dihydroxytryptamine (5,7-DHT) has been postulated to involve alkylation of neuronal proteins by its autooxidation product, which is believed to be corresponding p-quinone imine (5,7-DHTQ).To more precisely elucidate the mechanism of autoxidation of 5,7-DHT and its molecular mechanism of action in vivo, a series of methyl-substituted 5,7-DHT's, namely, 4-Me-, 6-Me-, and 4,6-Me2-5,7-DHT's (21a-c, respectively), were designed and synthesized as probes.The indole nucleus of these probes was constructed by the reductive cyclization of the corresponding 2,β-dinitrostyrene and the aminoethyl side chain was introduced via gramine methiodides.Cyclic voltammetric analysis of 5,7-DHT and 21a-c in 0.1 M H2SO4 and pH 4.0 and 7.4 buffers indicated that the primary product of electrochemical oxidation from each compound is the corresponding p-quinone imine which is very short lived ( 1 s).Like 5,7-DHT, 21a-c exhibited phenol-keto tautomerism but 21a and 21c did so to a much smaller extent as determined by UV and NMR spectroscopic methods.The predominant nonphenolic tautomeric form of 5,7-DHT, out of eight possible, was shown to be 27 (R1=R2=H).Polarographic measurements showed that, like 5,7-DHT, 21a-c react with O2 in a bimolecular fashion.Consideration of all the data indicates that the initial product of autoxidation in all cases is apparently a 4-hydroperoxy derivative.Only in the case of 5,7-DHT and 21b, the initially formed hydroperoxides break down to give colored products.These products were not stable enough to be isolated, but their UV-visible spectra correlate very well with similar known structures.The structure of this product in the case of 5,7-DHT is postulated to be the (4,7)p-quinone of 4,5,7-trihydroxytryptamine (4,5,7-THTQ, 35, R=H).The results of this study further indicate that in the autoxidation of 5,7-DHT, the p-quinone imine (5,7-DHTQ) is almost certainly not the primary product nor is it a transient intermediate in the formation of 4,5,7-THTQ. 4,5,7-THTQ also is unstable and appears to undergo further transformations at pH 7.4.