476159-75-8

Basic information

• Product Name: ethyl 3-hydroxy-3-(2-naphthyl)-1-pyrrolidinecarboxylate
• Synonyms: ethyl 3-hydroxy-3-(2-naphthyl)-1-pyrrolidinecarboxylate
• CAS NO: 476159-75-8
• Molecular Weight: 285.343
• Mol File: 476159-75-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ethyl 3-hydroxy-3-(2-naphthyl)-1-pyrrolidinecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-hydroxy-3-(2-naphthyl)-1-pyrrolidinecarboxylate(476159-75-8)
• EPA Substance Registry System: ethyl 3-hydroxy-3-(2-naphthyl)-1-pyrrolidinecarboxylate(476159-75-8)

Safety Data

• Hazardous Substances Data: 476159-75-8(Hazardous Substances Data)

Upstream product

• 14891-10-2 ethyl-3-oxo-1-pyrrolidinecarboxylate 
• 21473-01-8 2-naphthalenylmagnesium bromide 

Relevant articles and documents

3-Pyrrolines are mechanism-based inactivators of the quinone-dependent amine oxidases but only substrates of the flavin-dependent amine oxidases

We previously reported that 3-pyrroline and 3-phenyl-3-pyrroline effect a time-dependent inactivation of the copper-containing quinone-dependent amine oxidase from bovine plasma (BPAO) (Lee et al. J. Am. Chem. Soc. 1996, 118, 7241-7242). Quinone cofactor model studies suggested a mechanism involving stoichiometric turnover to a stable pyrrolylated cofactor. Full details of the model studies are now reported along with data on the inhibition of BPAO by a family of 3-aryl-3-pyrrolines (aryl = substituted phenyl, 1-naphthyl, 2-naphthyl), with the 4-methoxy-3-nitrophenyl analogue being the most potent. At the same time, the parent 3-phenyl analogue is a pure substrate for the flavin-dependent mitochondrial monoamine oxidase B from bovine liver. Spectroscopic studies (including resonance Raman) on BPAO inactivated by the 4-methoxy-3-nitrophenyl analogue are consistent with covalent derivatization of the 2,4,5-trihydroxyphenylalanine quinone (TPQ) cofactor. The distinction of a class of compounds acting as an inactivator of one amine oxidase family and a pure substrate of another amine oxidase family represents a unique lead to the development of selective inhibitors of the mammalian copper-containing amine oxidases.