645388-69-8

Basic information

• Product Name: 6-methoxy-2-phenyl-3,4-dihydroisoquinolin-1(2H)-one
• Synonyms: 6-methoxy-2-phenyl-3,4-dihydroisoquinolin-1(2H)-one
• CAS NO: 645388-69-8
• Molecular Weight: 253.301
• Mol File: 645388-69-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 6-methoxy-2-phenyl-3,4-dihydroisoquinolin-1(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methoxy-2-phenyl-3,4-dihydroisoquinolin-1(2H)-one(645388-69-8)
• EPA Substance Registry System: 6-methoxy-2-phenyl-3,4-dihydroisoquinolin-1(2H)-one(645388-69-8)

Safety Data

• Hazardous Substances Data: 645388-69-8(Hazardous Substances Data)

Upstream product

• 591-50-4 iodobenzene 
• 22246-12-4 6-methoxy-1,2,3,4-tetrahydro-1-oxoisoquinoline 

Downstream Products

• 1380397-97-6 2-(4-bromophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1219741-54-4 4′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-2-ol 
• 645400-94-8 1-[4-(2-azepan-1-yl-ethoxy)-phenyl]-6-methoxy-1-methyl-2-phenyl-1,2,3,4-tetrahydro-isoquinoline 
• 645398-54-5 6-methoxy-1-methyl-2-phenyl-1-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-1,2,3,4-tetrahydro-isoquinoline 
• 645395-22-8 6-methoxy-1-methyl-2-phenyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-1,2,3,4-tetrahydro-isoquinoline 
• 645389-24-8 1-(4-benzyloxy-phenyl)-6-methoxy-1-methyl-2-phenyl-1,2,3,4-tetrahydro-isoquinoline 
• 645393-20-0 4-(6-methoxy-1-methyl-2-phenyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)-phenol 
• 96719-60-7 1-(4-bromophenyl)-6-methoxy-2-phenyl-3,4-dihydro-1H-isoquinoline 

Relevant articles and documents

AMINE COMPOUND FOR INHIBITING SSAO / VAP-1 AND USE THEREOF

An amine compound serving as a semicarbazide-sensitive amine oxidase (SSAO) and/or vascular adhesion protein-1 (VAP-1) inhibitor, a pharmaceutical composition, and an application thereof in medicines that can be used for treating inflammation and/or inflammation related diseases, diabetes and/or a disease related diabetes, psychiatric disorder, ischemic disease, vascular disease, fibrosis, or tissue transplant rejection.

Reactions Catalysed by a Binuclear Copper Complex: Relay Aerobic Oxidation of N-Aryl Tetrahydroisoquinolines to Dihydroisoquinolones with a Vitamin B1 Analogue

N-Aryl tetrahydroisoquinolines were oxidised to dihydroisoquinolones through the relay catalysis of a binuclear paddle-wheel copper complex and a vitamin B1 analogue with oxygen as oxidant. Mechanistic studies revealed that the copper catalyst oxidises amines to the corresponding iminium salts, which are then oxygenated to lactam products by catalysis of the vitamin B1 analogue.

Estrogen receptor modulators: Identification and structure-activity relationships of potent ERα-selective tetrahydroisoquinoline ligands

As part of a program aimed at the development of selective estrogen receptor modulators (SERMs), tetrahydroisoquinoline derivative 27 was discovered by high throughput screening. Successive replacements of the p-F substituent of 27 by an aminoethoxy side chain and of the 1-H of the tetrahydroisoquinoline core by a 1-Me group provided analogues 19 and 20. These compounds showed potencies in a cell-based reporter gene assay (ERE assay) varying between 0.6 and 20 nM and displayed antagonist behaviors in the MCF-7 human breast adenocarcinoma cell line with IC50s in the range of 2-36 nM. The effect of N-phenyl substituents on the activity and pharmacokinetic properties of tetrahydroisoquinoline analogues was explored. As a result of this investigation, two potent derivatives bearing a p-F N-aryl group, 19c and 20c, were discovered as candidates suitable for further profiling. To gain insight into the ligand-receptor interaction, the X-ray crystallographic structure of the 1-H tetrahydroisoquinoline derivative (R)-18a in complex with ERα-ligand binding domain (LBD)301-553/C→S triple mutant was solved to 2.28 A?. An overlay of this X-ray crystal structure with that reported for the complex of ERαLBD301-553/carboxymethylated C and raloxifene (5) shows that both compounds bind to the same cleft of the receptor and display comparable binding modes, with differences being observed in the conformation of their "D-ring" phenyl groups.