6857-58-5

Basic information

• Product Name: 6-benzyloxy-7-methoxy-1-methyl-3,4-dihydroisoquinoline
• Synonyms: 6-benzyloxy-7-methoxy-1-methyl-3,4-dihydroisoquinoline
• CAS NO: 6857-58-5
• Molecular Weight: 281.354
• Mol File: 6857-58-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 6-benzyloxy-7-methoxy-1-methyl-3,4-dihydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-benzyloxy-7-methoxy-1-methyl-3,4-dihydroisoquinoline(6857-58-5)
• EPA Substance Registry System: 6-benzyloxy-7-methoxy-1-methyl-3,4-dihydroisoquinoline(6857-58-5)

Safety Data

• Hazardous Substances Data: 6857-58-5(Hazardous Substances Data)

Upstream product

• 55161-43-8 N-{2-[3-(benzyloxy)-4-methoxyphenyl]ethyl}acetamide 
• 621-59-0 isovanillin 
• 876479-68-4 3-(3-benzyloxy-4-methoxy-phenyl)-propionic acid hydrazide 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 100-44-7 benzyl chloride 
• 36455-21-7 3-benzyloxy-4-methoxyphenylethylamine 
• 63909-29-5 3-benzyloxy-4-methoxy-β-nitrostyrene 

Downstream Products

• 68360-24-7 4-(6-Benzyloxy-7-methoxy-3,4-dihydro-isoquinolin-1-yl)-butyric acid methyl ester 
• 132148-47-1 1-[5-(6-Benzyloxy-7-methoxy-1-methylene-3,4-dihydro-1H-isoquinoline-2-carbonyl)-pyridin-3-yl]-ethanone 
• 4602-70-4 3,4-dihydro-6-hydroxy-7-methoxy-1-methylisoquinoline 
• 51745-26-7 (+/-)-6-benzyloxy-1,2,3,4-tetrahydro-7-methoxy-1-methylisoquinoline 
• 98988-23-9 (+/-)-O-benzylisobharatamine 
• 89240-64-2 9-Benzyloxy-10-methoxy-1,2,3,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-4-one 
• 89-31-6 rac-salsoline 
• 132148-49-3 11-Acetyl-3-benzyloxy-2-methoxy-5,6-dihydro-6a,9-diaza-benzo[a]anthracen-7-one 
• 132148-48-2 9-Acetyl-3-benzyloxy-2-methoxy-5,6-dihydro-6a,11-diaza-benzo[a]anthracen-7-one 
• 1064203-04-8 (+/-)-7-methoxy-1-methyl-6-sulfamoyloxy-2-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline 
• 1064203-01-5 (+/-)-2-(3-methoxybenzyl)-7-methoxy-1-methyl-6-sulfamoyloxy-1,2,3,4-tetrahydroisoquinoline 
• 1064202-99-8 (+/-)-6-hydroxy-7-methoxy-1-methyl-2-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline 
• 1064202-97-6 (+/-)-6-hydroxy-7-methoxy-2-(3-methoxybenzyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline 
• 1064202-92-1 6-benzyloxy-7-methoxy-1-methyl-2-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Synthesis, antitubulin, and antiproliferative sar of c3/c1-substituted tetrahydroisoquinolines

The syntheses and antiproliferative activities of novel substituted tetrahydroisoquinoline derivatives and their sulfamates are discussed. Biasing of conformational populations through substitution on the tetrahydroisoquinoline core at C1 and C3 has a pro

Syntheses and antitumor targeting G1 phase of the cell cycle of benzoyldihydroisoquinolines and related 1-substituted isoquinolines

A series of 1-substituted 3,4-dihydroisoquinolines were synthesized and tested in vitro against the leukemia L 1210 cell line to evaluate their ability to perturb the cell cycle by arresting cells in the G1 phase. 1-Benzoylimines, 1-phenylimines, and 1-alkylimines were synthesized. The most powerful cytotoxic derivatives, 1-benzoyl-3,4-dihydroisoquinolines (1-26), were obtained from amides I via 1-benzyl-3,4-dihydroisoquinoline in good yield by a direct selective oxidation of the benzylic carbon of the corresponding imines through 10% Pd/C in acetonitrile. SAR studies let us to identify the essential structural features for cytotoxic activity. The most bioactive compounds (with IC50 5μM) were BzDHIQ (13, 22, 21, 8, 9, 11, 1, 20, 6, and 19), and they are characterized by the following: (i) An α-ketoimine moiety is necessary for potent antiproliferative activity (1-phenyl- and 1-alkyl-3,4-dihydroisoquinoline derivatives, 34-40, are less active). (ii) An hydrophobic, benzyloxy, alkyloxy, or allyloxy group at the C-6 position seems to be relevant for cytotoxicity. (iii) Regarding the influence of the benzoylic moiety, both the unsubstituted (13, 8, 9, 11, 1, and 6) and the 3′-monosubstituted (22, 21, 20, and 19) compounds were more potent than compounds with other substitutions.