219753-99-8

Usage

Uses

Used in Medicinal Chemistry:
(1S,2S,4S,7R)-6-aza-3,3-dimethyl-8-oxa-7-phenyltricyclo<4.3.0.0>nonan-5-one is used as a potential pharmaceutical candidate for various applications due to its unique structure and functional groups. It may exhibit biological activity, making it a promising compound for further research and exploration in the field of medicinal chemistry.

Upstream product

• 134107-65-6 (3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one 
• 74-88-4 methyl iodide 
• 103201-79-2 (3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 
• 1530-33-2 isopropyltriphenylphosphonium bromide 

Downstream Products

• 219754-08-2 Piv-PTL-PTL-OBn 
• 219754-03-7 (1R,2S,5S)-6,6-Dimethyl-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-benzyl ester 3-tert-butyl ester 
• 219754-05-9 (1R,2S,5S)-3-(2,2-Dimethyl-propionyl)-6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid benzyl ester 
• 219754-07-1 (1R,2S,5S)-6,6-Dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid benzyl ester 
• 219754-02-6 (1R,2S,5S)-3-(tert-butoxycarbonyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 

Relevant academic research and scientific papers

Discovery of (1R,5S)-N-[3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3- [2(S)-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6, 6-dimethyl-3-azabicyclo[3.1.0]hexan-2(S)-carboxamide (SCH 503034), a selective, potent, orally bioavailable hepatitis C virus NS3 protease inhibitor: A potential therapeutic agent for the treatment of hepatitis C infection

Hepatitis C virus (HCV) infection is the major cause of chronic liver disease, leading to cirrhosis and hepatocellular carcinoma, which affects more than 170 million people worldwide. Currently the only therapeutic regimens are subcutaneous interferon-α or polyethylene glycol (PEG)-interferon-α alone or in combination with oral ribavirin. Although combination therapy is reasonably successful with the majority of genotypes, its efficacy against the predominant genotype (genotype 1) is moderate at best, with only about 40% of the patients showing sustained virological response. Herein, the SAR leading to the discovery of 70 (SCH 503034), a novel, potent, selective, orally bioavailable NS3 protease inhibitor that has been advanced to clinical trials in human beings for the treatment of hepatitis C viral infections is described. X-ray structure of inhibitor 70 complexed with the NS3 protease and biological data are also discussed.

Cyclopropanation reactions of pyroglutamic acid-derived synthons with akylidene transfer reagents

The cyclopropanation of unsaturated lactams 1 and 3 derived from pyroglutamic acid with nucleophilic alkylidene transfer reagents is investigated. Good-to-modest yields of cyclopropanes were obtained with most sulfur ylides explored. Syn/anti selectivity was found to be dependent on the synthon as well as the sulfur ylide. This cyclopropanation methodology is used in the synthesis of arginine and glutamic acid analogues.