911422-98-5

Basic information

• Product Name: tert-butyl (1S,4R,5R,7S)-7-amino-5-(3-isopropoxyphenyl)-4-methyl-2-azabicyclo[3.3.1]nonane-2-carboxylate
• Synonyms: tert-butyl (1S,4R,5R,7S)-7-amino-5-(3-isopropoxyphenyl)-4-methyl-2-azabicyclo[3.3.1]nonane-2-carboxylate
• CAS NO: 911422-98-5
• Molecular Weight: 388.55
• Mol File: 911422-98-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: tert-butyl (1S,4R,5R,7S)-7-amino-5-(3-isopropoxyphenyl)-4-methyl-2-azabicyclo[3.3.1]nonane-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (1S,4R,5R,7S)-7-amino-5-(3-isopropoxyphenyl)-4-methyl-2-azabicyclo[3.3.1]nonane-2-carboxylate(911422-98-5)
• EPA Substance Registry System: tert-butyl (1S,4R,5R,7S)-7-amino-5-(3-isopropoxyphenyl)-4-methyl-2-azabicyclo[3.3.1]nonane-2-carboxylate(911422-98-5)

Safety Data

• Hazardous Substances Data: 911422-98-5(Hazardous Substances Data)

Upstream product

• 911422-92-9 2-[(1S,4R,5S,7S)-5-(3-isopropoxyphenyl)-2,4-dimethyl-2-azabicyclo[3.3.1]non-7-yl]-1H-isoindole-1,3(2H)-dione 
• 911422-93-0 2-[(1S,4R,5S,7S)-5-(3-isopropoxyphenyl)-4-methyl-2-azabicyclo[3.3.1]non-7-yl]-1H-isoindole-1,3(2H)-dione 
• 911423-22-8 7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-(3-isopropoxy-phenyl)-4-methyl-2-aza-bicyclo[3.3.1]nonane-2-carboxylic acid tert-butyl ester 

Downstream Products

• 911423-23-9 tert-butyl (1S,4R,5R,7S)-5-(3-isopropoxyphenyl)-4-methyl-7-[(2-methyl-2-phenylpropanoyl)amino]-2-azabicyclo[3.3.1]nonane-2-carboxylate 
• 911423-00-2 N-[(1S,4R,5R,7S)-5-(3-isopropoxyphenyl)-4-methyl-2-(2-phenoxyethyl)-2-azabicyclo[3.3.1]non-7-yl]-2-methyl-2-phenylpropanamide 
• 911422-99-6 N-[(1S,4R,5R,7S)-5-(3-isopropoxyphenyl)-4-methyl-2-azabicyclo[3.3.1]non-7-yl]-2-methyl-2-phenylpropanamide 
• 911423-24-0 N-[(1S,4R,5R,7S)-5-(3-hydroxyphenyl)-4-methyl-2-azabicyclo[3.3.1]non-7-yl]-2-methyl-2-phenylpropanamide 
• 911423-02-4 tert-butyl (1S,4R,5R,7S)-5-(3-isopropoxyphenyl)-4-methyl-7-{[(1-phenyl-1-cyclopentyl)carbonyl]amino}-2-azabicyclo[3.3.1]nonane-2-carboxylate 

Relevant articles and documents

Highly potent and selective phenylmorphan-based inverse agonists of the opioid δ receptor

We recently reported the discovery of (+)-5-(3-hydroxyphenyl)-4-methyl-2- (3-phenylpropyl)-2-azabicyclo-[3.3.1]non-7-yl-(1-phenyl-1-cyclopentane) carboxamide [(+)-KF4, (+)-5] as a novel chemotype possessing potent antagonist activity at the δ opioid receptor. Additional SAR studies involving changes to both the 2-amino and 7-amido N-substituents using this same (+)-morphan scaffold have revealed compounds with improved potency and selectivity for the δ opioid receptor. The highly potent and selective 2,2-dimethylphenylacetamide analogue (+)-N-[(1S,4R,5R,7S)-5-(3-hydroxyphenyl)-4- methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]non-7-yl]-2-methyl-2- phenylpropanamide (13d, delmorphan-A) showed picomolar inhibitory potency (Ke = 0.1 nM) in the [35S]GTPγS functional assay with δ opioid receptor selectivity ratios of 103- and 132-fold versus the μ and κ opioid receptors, respectively. The compounds showed no agonist activity at any of the three opioid receptors; however, measurements of δ inverse agonist activity within this series illustrated a broad range of negative efficacy and IC50 values 650-fold more potent than the prototypical δ opioid receptor inverse agonist ICI 174 864 (22).