280559-71-9

Upstream product

• 280559-69-5 (2R,5R)-2-tert-butyl-5-[(1S,3R)-3-hydroxycyclopentyl]-5-phenyl-1,3-dioxolan-4-one 
• 203321-54-4 (2R,5R)-2-(t-butyl)-5-[(1S)-3-oxocyclopentyl]-5-phenyl-1,3-dioxolan-4-one 
• 116907-30-3 (2R,5R)-2-(tert-butyl)-5-phenyl-1,3-dioxolan-4-one 
• 930-30-3 cyclopent-2-enone 

Downstream Products

• 280559-73-1 (2R)-N-[1-(4-methyl-3-pentenyl)piperidin-4-yl]-2-[(1S,3S)-3-aminocyclopentyl]-2-hydroxy-2-phenylacetamide 
• 280559-72-0 (2R)-N-[1-(4-methyl-3-pentenyl)piperidin-4-yl]-2-[(1S,3S)-3-azidocyclopentyl]-2-hydroxy-2-phenylacetamide 

Relevant academic research and scientific papers

Discovery of a muscarinic M3 receptor antagonist with high selectivity for M3 over M2 receptors among 2-[(1S,3S)-3-sulfonylaminocyclopentyl]phenylacetamide derivatives.

In the course of developing a metabolically stable M3 receptor antagonist from the prototype antagonist, J-104129 (1), introduction of certain substituents into the cyclopentane ring of 1 was found to be effective not only in improving metabolic stability but also in greatly enhancing the subtype selectivity. Among the cyclopentane analogues, sulfonamide derivatives (10f) and (10g) displayed 160- and 310-fold selectivity for M3 over M2 receptors, and both were significantly more selective than the prototype antagonist (120-fold). Subsequent derivatization of the sulfonamide series led to the highly selective M3 receptor antagonists (10h, 10i and 10j) with >490-fold selectivity for M3 over M2 receptors. Among them, p-nitrophenylsulfonamide (J-107320, 10h) exhibited 1100-fold selectivity for M3 receptors (Ki = 2.5 nM) over M2 receptors (Ki = 2800 nM) in the human muscarinic receptor binding assay using [3H]-NMS as a radio ligand.