323183-79-5

Upstream product

• 545380-39-0 methyl (2R)-1-([(2S,4R)-4-tert-butoxy-1-(benzyloxycarbonyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carboxylate 
• 911296-66-7 methyl (2R)-1-([(2S,4R)-4-tert-butoxy-1-pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carboxylate 
• 900-91-4 3,3,3-triphenylpropionic acid 
• 545380-40-3 (R)-1-[(2S,4R)-4-tert-Butoxy-1-(3,3,3-triphenyl-propionyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carboxylic acid methyl ester 
• 182210-00-0 methyl (2R)-(benzyloxycarbonyl)pyrrolidine-2-carboxylate 
• 85201-91-8 (2S,4R)-4-tert-butoxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 
• 6404-31-5 Z-D-proline 
• 43041-12-9 methyl (2R)-pyrrolidine-2-carboxylate 

Downstream Products

• 323182-79-2 (2R)-1-{(2S,4R)-4-hydroxy-1-(3,3,3-triphenylpropanoyl)-pyrrolidin-2-yl}carbonyl-N-(4-piperidylmethyl)pyrrolidine-2-carboxamide 
• 323182-73-6 (2R)-1-{(2S,4R)-4-hydroxy-1-(3,3,3-triphenylpropanoyl)-pyrrolidin-2-yl}carbonyl-N-((3R)-3-piperidylmethyl)pyrrolidine-2-carboxamide 
• 323182-20-3 (2R)-1-{(2S,4R)-4-hydroxy-1-(3,3,3-triphenylpropanoyl)-pyrrolidin-2-yl}carbonyl-N-((3S)-3-piperidylmethyl)pyrrolidine-2-carboxamide 
• 545380-41-4 (S)-3-[({(R)-1-[(2S,4R)-4-tert-Butoxy-1-(3,3,3-triphenyl-propionyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carbonyl}-amino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester 
• 323183-51-3 (2R)-N-({(3R)-1-(tert-butoxycarbonyl)-3-piperidyl)methyl)-1-{(2S,4R)-4-(tert-butoxy)-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}-carbonylpyrrolidine-2-carboxamide 

Relevant academic research and scientific papers

Identification of a novel 4-aminomethylpiperidine class of M3 muscarinic receptor antagonists and structural insight into their M3 selectivity

Identification of a novel class of potent and highly selective M 3 muscarinic antagonists is described. First, the structure-activity relationship in the cationic amine core of our previously reported triphenylpropionamide class of M3 selective antagonists was explored by a small diamine library constructed in solid phase. This led to the identification of M3 antagonists with a novel piperidine pharmacophore and significantly improved subtype selectivity from a previously reported class. Successive modification on the terminal triphenylpropionamide part of the newly identified class gave 14a as a potent M3 selective antagonist that had > 100-fold selectivity versus the M1, M 2, M4, and M5 receptors (M3: K i = 0.30 nM, M1/M3 = 570-fold, M 2/M3 = 1600-fold, M4/M3 = 140-fold, M5/M3 = 12000-fold). The possible rationale for its extraordinarily higher subtype selectivity than reported M3 antagonists was hypothesized by sequence alignment of multiple muscarinic receptors and a computational docking of 14a into transmembrane domains of M3 receptors.

Identification of novel muscarinic M(3) selective antagonists with a conformationally restricted Hyp-Pro spacer.

The identification of potent and selective muscarinic M(3) antagonists that are based on the recently discovered triphenylpropioamide derivative, 1, and have a unique amino acid spacer group is described. The introduction of a hydroxyproline-proline group to the spacer site and the use of a propyl or cyclopropylmethyl group as the piperidine N-substituent led to the discovery of the novel M(3) selective antagonists [8c, 8g; K(i)700-fold, M(2)/M(3)>180-fold], which have a more rigid structure than 1.