573674-57-4

Basic information

• Product Name: 6-methoxy-2-(3-methoxyphenyl)-1-methyl-1-[4-(2-piperidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline
• Synonyms: 6-methoxy-2-(3-methoxyphenyl)-1-methyl-1-[4-(2-piperidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 573674-57-4
• Molecular Weight: 486.654
• Mol File: 573674-57-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 6-methoxy-2-(3-methoxyphenyl)-1-methyl-1-[4-(2-piperidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methoxy-2-(3-methoxyphenyl)-1-methyl-1-[4-(2-piperidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline(573674-57-4)
• EPA Substance Registry System: 6-methoxy-2-(3-methoxyphenyl)-1-methyl-1-[4-(2-piperidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline(573674-57-4)

Safety Data

• Hazardous Substances Data: 573674-57-4(Hazardous Substances Data)

Upstream product

• 573674-54-1 1-(4-benzyloxyphenyl)-6-methoxy-2-(3-methoxyphenyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline 
• 573674-53-0 6-methoxy-2-(3-methoxyphenyl)-3,4-dihydro-2H-isoquinolin-1-one 
• 22246-12-4 6-methoxy-1,2,3,4-tetrahydro-1-oxoisoquinoline 
• 2398-37-0 3-methoxyphenyl bromide 
• 2008-75-5 N-chloroethylpiperidine hydrochloride 
• 573674-55-2 4-[6-methoxy-2-(3-methoxyphenyl)-1-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]phenol 

Relevant articles and documents

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.