90821-77-5

Upstream product

• 66504-37-8 (1R,2S)-(+)-1-phenyl-1,2-cyclopropanedicarboximide 
• 14062-24-9 4-chloro-benzeneacetic acid, ethyl ester 
• 56695-75-1 (1R,2S)-(+)-1-(4-chlorophenyl)-1,2-cyclopropanedicarboxylic acid 
• 66673-12-9 (1R,5S)-1-(4-Chloro-phenyl)-3-aza-bicyclo[3.1.0]hexane-2,4-dione 
• 56695-75-1 (1R,2S)-1-(4-Chloro-phenyl)-cyclopropane-1,2-dicarboxylic acid 
• 683246-91-5 N-(but-3-en-1-yl)-4-methyl-N-(phenylethynyl)benzenesulfonamide 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 153275-06-0 (1R,5S)-1-phenyl-3-azabicyclo[3.1.0]hexan-2-one 
• 17559-40-9 (1S,2R)-1-(4-Chloro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester 
• 5445-25-0 ethyl 2-bromo-2-(4-chlorophenyl)acetate 

Relevant academic research and scientific papers

Stereoselective construction of fused cyclopropane from ynamide and its application to synthesis of small drug candidate molecules

Herein, we report the development of an asymmetric intramolecular cyclopropanation reaction under silver catalysis. The strategy is based on diazo-free silver–carbene generation, providing γ-lactam fused cyclopropane in an enantioenriched form. The ring s

1-Aryl-3-azabicyclohexanes, a New Series of Nonnarcotic Analgesic Agents

A series of 1-aryl-3-azabicyclohexanes was synthesized by hydride reduction of 1-arylcyclopropanedicarboximides.Hydroxyphenyl analogues 20, 22, and 24 were prepared by EtSNa-DMF ether cleavage of the corresponding methoxyphenyl analogues 2m, 2n, and 23, respectively, with the secondary amines 20 and 22 going through the N-formyl intermediates 19 and 21.The p-ethoxy analogue 26 was obtained by O-ethylation of 19, followed by base hydrolysis of the amide 25.The greatest analgesic potency in mouse writhing and rat paw-pain assays was observed for para-substituted compounds.Bicifadine, 1-(4-methylphenyl)-3-azabicyclohexane (2b), was the most potent member of the series and is presently undergoing clinical trials in man.Analgesic activity of 2b is limited to the (+) enantiomer 2v, which has the 1R,5S absolute configuration as determined by single-crystal X-ray analysis.The N-methyl analogue (27d) of 2b showed significant analgesic potency, whereas the N-allyl (27a), N-(cyclopropylmethyl) (27b), and N-(n-hexyl) (27c) analogues were inactive.Bicifadine (2b) showed a nonnarcotic profile different from analogous azabicycloalkane and 3-phenylpyrrolidine analgesics.