881686-07-3

Upstream product

• 444904-04-5 (-)-(1R,4S,5S)-5-[3-(1-methylethoxy)phenyl]-2,4-dimethyl-2-azabicyclo[3.3.1]nonan-7-one 
• 881686-04-0 tert-butyl (1R,4S,5R,7R)-7-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-(3-isopropoxyphenyl)-4-methyl-2-azabicyclo[3.3.1]nonane-2-carboxylate 
• 881686-00-6 2-[(1R,4S,5R,7R)-5-(3-isopropoxyphenyl)-2,4-dimethyl-2-azabicyclo[3.3.1]non-7-yl]-1H-isoindole-1,3(2H)-dione 
• 881686-01-7 2-[(1R,4S,5R,7R)-5-(3-isopropoxyphenyl)-4-methyl-2-azabicyclo[3.3.1]non-7-yl]-1H-isoindole-1,3(2H)-dione 
• 881686-05-1 tert-butyl (1R,4S,5R,7R)-7-amino-5-(3-isopropoxyphenyl)-4-methyl-2-azabicyclo[3.3.1]nonane-2-carboxylate 
• 881685-98-9 (1R,4S,5R)-5-(3-isopropoxyphenyl)-2,4-dimethyl-2-azabicyclo[3.3.1]nonan-7-one oxime 
• 881685-99-0 (1R,4S,5S,7R)-5-(3-isopropoxyphenyl)-2,4-dimethyl-2-azabicyclo[3.3.1]nonan-7-amine 
• 846576-15-6 3-(3,4-dihydro-1H-isoquinolin-2-yl)propionic acid hydrochloride 
• 881686-06-2 tert-butyl (1R,4S,5R,7R)-7-{[3-(3,4-dihydroisoquinolin-2(1H)-yl)propionoyl]amino}-5-(3-isopropoxyphenyl)-4-methyl-2-azabicyclo[3.3.1]nonane-2-carboxylate 

Relevant academic research and scientific papers

N-substituted 4β-methyl-5-(3-hydroxyphenyl)-7α-amidomorphans are potent, selective κ opioid receptor antagonists

In a previous study, we identified (-)-N-[(1R,4S,5S,7R)-5-(3-hydroxyphenyl) -4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]non-7-yl]-3-(1-piperidinyl) propanamide (5a, KAA-1) as the first potent and selective κ opioid receptor antagonist from the 5-(3-hydroxyphenyl)morphan class of opioids. In this study we report an improved synthesis of this class of compounds. The new synthetic method was used to prepare analogues 5b-r where the morphan N-substituent and 7α-amido group were varied. Most of the analogues showed sub-nanomolar potency for the κ opioid receptor and were highly selective relative to the μ and δ opioid receptors. (-)-3-(3,4- Dihydroisoquinolin-2(1H)-yl)-N-{(1R,4S,5S,7R)-5-(3-hydroxyphenyl) -4-methyl-2-[2-(2-methylphenyl)ethyl]-2-azabicyclo[3.3.1]non-7-yl}propanamide (5n, MTHQ) is at least as potent and selective as nor-BNI as a κ opioid receptor antagonist in the [35S]GTP-γ-S in vitro functional test.