35596-93-1

Upstream product

• 4397-53-9 p-benzyloxybenzaldehyde 
• 82099-81-8 1-(benzyloxy)-4-(2-methoxyethenyl)benzene 
• 23506-76-5 (±)-ethyl 7-(benzyloxy)-1-(4-(benzyloxy)benzyl)-6-methoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 22231-61-4 2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 1700-33-0 N-ethoxycarbonyl-4-benzyloxy-3-methoxyphenethylamine 
• 63909-38-6 1-(benzyloxy)-2-methoxy-4-[(E)-2-nitroethenyl]benzene 
• 1263210-00-9 (R)-1-(4-benzyloxybenzyl)-2-formyl-6-methoxy-7-benzyloxy-1,2,3,4-tetrahydro-isoquinoline 

Downstream Products

• 35596-93-1 (+)-di-O-bisbenzyl-N-methylcoclaurine 
• 35596-93-1 (-)-di-O-bisbenzyl-N-methylcoclaurine 
• 3423-07-2 (S)-N-methylcoclaurine 
• 5096-70-8 (-)-(R)-(N)-methylcoclaurine 
• 47791-90-2 (R)-7-(benzyloxy)-1-(4-(benzyloxy)-3-bromobenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Gene editing and synthetically accessible inhibitors reveal role for TPC2 in HCC cell proliferation and tumor growth

The role of two-pore channel 2 (TPC2), one of the few cation channels localized on endolysosomal membranes, in cancer remains poorly understood. Here, we report that TPC2 knockout reduces proliferation of cancer cells in vitro, affects their energy metabolism, and successfully abrogates tumor growth in vivo. Concurrently, we have developed simplified analogs of the alkaloid tetrandrine as potent TPC2 inhibitors by screening a library of synthesized benzyltetrahydroisoquinoline derivatives. Removal of dispensable substructures of the lead molecule tetrandrine increases antiproliferative properties against cancer cells and impairs proangiogenic signaling of endothelial cells to a greater extent than tetrandrine. Simultaneously, toxic effects on non-cancerous cells are reduced, allowing in vivo administration and revealing a TPC2 inhibitor with antitumor efficacy in mice. Hence, our study unveils TPC2 as valid target for cancer therapy and provides easily accessible tetrandrine analogs as a promising option for effective pharmacological interference.

Formal synthesis of the bisbenzylisoquinoline alkaloid berbamunine by asymmetric substitution of chiral organolithium compounds

Asymmetric alkylation of enantiomeric tetrahydroisoquinolyl oxazolines was achieved with 96-97% diastereoselectivity. Removal of the oxazoline chiral auxiliary and further transformations provide a straightforward synthesis of the two synthetic intermediates that were previously synthesized by resolution, and which comprise a formal synthesis of berbamunine by Ullman coupling. ARKAT-USA, Inc.

THE BIOSYNTHESIS OF THE ALKALOIDS OF CROTON SPARSIFLORUS MORONG

Incorporation of tyrosine, dopa, dopamine, 4-hydroxyphenylpyruvic acid, (+/-)-, norcoclaurine-1-carboxylic acid, -norcoclaurine, -coclaurine, and -N-methylcoclaurine into N-methylcrotsparine, N-methylcrotsparinine and N-methylsparsiflorine in Croton sparsiflorus Morong has been studied.The evidence supports the direct oxidative coupling of (+)-, and (-)-N-methylcoclaurines to give N-methylcrotsparine and N-methylcrotsparinine, respectively.Tracer experiment show that N-methylcrotsparine undergoes dienone-phenol rearrangement to give N-methylsparsiflorine.A doublelabelling experiment with (+/-)-Nmethylcoclaurine demonstrated that the H atom at the asymmetric centre in the 1-benzylisoquinoline precursor is retained in the bioconversion.The intermediacy of norcoclaurine-1-carboxylic acid and specific incorporation of dehydro-N-methylcoclaurinium salt into the bases have been demonstrated.