130497-48-2

Basic information

• Product Name: 2-(4-Cyclohexyl-phenyl)-1-(2-pyrrolidin-1-ylmethyl-piperidin-1-yl)-ethanone
• Synonyms: 2-(4-Cyclohexyl-phenyl)-1-(2-pyrrolidin-1-ylmethyl-piperidin-1-yl)-ethanone
• CAS NO: 130497-48-2
• Molecular Weight: 368.563
• Mol File: 130497-48-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-(4-Cyclohexyl-phenyl)-1-(2-pyrrolidin-1-ylmethyl-piperidin-1-yl)-ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Cyclohexyl-phenyl)-1-(2-pyrrolidin-1-ylmethyl-piperidin-1-yl)-ethanone(130497-48-2)
• EPA Substance Registry System: 2-(4-Cyclohexyl-phenyl)-1-(2-pyrrolidin-1-ylmethyl-piperidin-1-yl)-ethanone(130497-48-2)

Safety Data

• Hazardous Substances Data: 130497-48-2(Hazardous Substances Data)

Upstream product

• 61578-80-1 (4-cyclohexyl-phenyl)-acetyl chloride 
• 100158-63-2 2-[(1-Pyrrolidinyl)methyl]piperidine 
• 4043-87-2 pipecolic Acid 
• 130497-14-2 (+/-)-[(N-ethoxycarbonyl)piperidine]-2-carboxylic acid 
• 130605-98-0 1-(2-piperidinylcarbonyl)pyrrolidine 
• 130606-00-7 piperidine-2-carbonyl chloride 
• 35889-00-0 (4-cyclohexyl-phenyl)-acetic acid 

Relevant articles and documents

(2S)-1-(arylacetyl)-2-(aminomethyl)piperidine derivatives: Novel, highly selective κ opioid analgesics

This paper describes the synthesis and structure-activity relationships as κ opioid analgesics of a novel class of 1-(arylacetyl)-2-(aminomethyl)piperidine derivatives (8). The active conformation of the pharmacophore, with a torsional angle (N1C2C7N8) of 60°, was defined with computational studies and 1H NMR. A quantitative structure-activity relationship study of the arylacetic moiety substitution indicated that the presence of an electron-withdrawing and lipophilic substituent in para and/or meta positions is required for good analgesic activity and κ affinity. The lead compounds (2S)-1-[(3,4-dichlorophenyl)acetyl]-2-(pyrrolidin-1-ylmethyl) piperidine hydrochloride (14) and (2S)-1-[[4-(trifluoromethyl)phenyl]acetyl]-2-(pyrrolidin-1- ylmethyl)piperidine hydrochloride (21) are the most κ/μ selective (respectively 6500:1 and 4100:1) and among the most potent (K(i) κ 0.24 and 0.57 nM, respectively) κ ligands identified so far. In the mouse tail flick model of antinociception, compound 14 (ED50 = 0.05 mg/kg sc) was 25 times more potent than morphine and 16 times more potent than the standard κ ligand U-50488.