1332870-60-6

Basic information

• Product Name: (3R)-7-hydroxy-N-[(1S)-1-{[(3S)-4-(3-hydroxyphenyl)-3-methylpiperazin-1-yl]methyl}-2-methylpropyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
• Synonyms: (3R)-7-hydroxy-N-[(1S)-1-{[(3S)-4-(3-hydroxyphenyl)-3-methylpiperazin-1-yl]methyl}-2-methylpropyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
• CAS NO: 1332870-60-6
• Molecular Weight: 452.597
• Mol File: 1332870-60-6.mol

Chemical Properties

• CAS DataBase Reference: (3R)-7-hydroxy-N-[(1S)-1-{[(3S)-4-(3-hydroxyphenyl)-3-methylpiperazin-1-yl]methyl}-2-methylpropyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: (3R)-7-hydroxy-N-[(1S)-1-{[(3S)-4-(3-hydroxyphenyl)-3-methylpiperazin-1-yl]methyl}-2-methylpropyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide(1332870-60-6)
• EPA Substance Registry System: (3R)-7-hydroxy-N-[(1S)-1-{[(3S)-4-(3-hydroxyphenyl)-3-methylpiperazin-1-yl]methyl}-2-methylpropyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide(1332870-60-6)

Safety Data

• Hazardous Substances Data: 1332870-60-6(Hazardous Substances Data)

Upstream product

• 1238951-39-7 (S)-tert-butyl-4-(3-methoxyphenyl)-3-methylpiperazine-1-carboxylate 
• 1332870-59-3 3-{(2S)-4-[(2S)-2-amino-3-methylbutyl]-2-methylpiperazin-1-yl}phenol 
• 214630-00-9 (3R)-2-(tert-butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 1238951-44-4 (S)-3-(2-methylpiperazin-1-yl)phenol 
• 13734-41-3 t-Boc-L-valine 

Relevant articles and documents

Discovery of N-{4-[(3-hydroxyphenyl)-3-methylpiperazin-1-yl]methyl-2- methylpropyl}-4-phenoxybenzamide analogues as selective kappa opioid receptor antagonists

There is continuing interest in the discovery and development of new κ opioid receptor antagonists. We recently reported that N-substituted 3-methyl-4-(3-hydroxyphenyl)piperazines were a new class of opioid receptor antagonists. In this study, we report the syntheses of two piperazine JDTic-like analogues. Evaluation of the two compounds in an in vitro [35S] GTPγS binding assay showed that neither compound showed the high potency and κ opioid receptor selectivity of JDTic. A library of compounds using the core scaffold 21 was synthesized and tested for their ability to inhibit [35S]GTPγS binding stimulated by the selective κ opioid agonist U69,593. These studies led to N-[(1S)-1-{[(3S)-4-(3-hydroxyphenyl)-3- methylpiperazin-1-yl]methyl}-2-methylpropyl]-4-phenoxybenzamide (11a), a compound that showed good κ opioid receptor antagonist properties. An SAR study based on 11a provided 28 novel analogues. Evaluation of these 28 compounds in the [35S]GTPγS binding assay showed that several of the analogues were potent and selective κ opioid receptor antagonists.

ARYLPIPERAZINE OPIOID RECEPTOR ANTAGONISTS

Provided are opioid receptor antagonists represented by the formula (I) where R, Y3, R1, R2, R3, R4 and R5 are as defined herein.