1439366-92-3

Basic information

• Product Name: 5-phenylpentyl N-methyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]-carbamate
• Synonyms: 5-phenylpentyl N-methyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]-carbamate
• CAS NO: 1439366-92-3
• Molecular Weight: 305.374
• Mol File: 1439366-92-3.mol

Chemical Properties

• CAS DataBase Reference: 5-phenylpentyl N-methyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]-carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: 5-phenylpentyl N-methyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]-carbamate(1439366-92-3)
• EPA Substance Registry System: 5-phenylpentyl N-methyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]-carbamate(1439366-92-3)

Safety Data

• Hazardous Substances Data: 1439366-92-3(Hazardous Substances Data)

Upstream product

• 10521-91-2 5-phenylpentan-1-ol 
• 2270-20-4 5-Phenylpentanoic acid 
• 1439367-96-0 (2R,3S)-3-hydroxy-2-[methyl-(5-phenylpentoxycarbonyl)-amino]-butanoic acid 
• 170872-87-4 (2R,3S)-2-[tert-butoxycarbonyl-(methyl)-amino]-3-hydroxy-butanoic acid 
• 226067-37-4 (2R,3S)-3-benzyloxy-2-[tert-butoxycarbonyl-(methyl)-amino]-butanoic acid 

Relevant articles and documents

Disubstituted beta-lactones as inhibitors of N-acylethanolamine acid amidase (NAAA)

The present invention provides compounds and pharmaceutical compositions for inhibiting N-acylethanolamine acid amidase (NAAA). Inhibition of NAAA is contemplated as a method to sustain the levels of palmitoylethanolamide (PEA) and oleylethanolamide (OEA), two substrates of NAAA, in conditions characterized by reduced concentrations of PEA and OEA. The invention also provides methods for treating inflammatory diseases and pain, and other disorders in which decreased levels of PEA and OEA are associated with the disorder.

Synthesis and structure-activity relationship (SAR) of 2-methyl-4-oxo-3- oxetanylcarbamic acid esters, a class of potent N-acylethanolamine acid amidase (NAAA) inhibitors

N-Acylethanolamine acid amidase (NAAA) is a lysosomal cysteine hydrolase involved in the degradation of saturated and monounsaturated fatty acid ethanolamides (FAEs), a family of endogenous lipid agonists of peroxisome proliferator-activated receptor-α, which include oleoylethanolamide (OEA) and palmitoylethanolamide (PEA). The β-lactone derivatives (S)-N-(2-oxo-3-oxetanyl)-3-phenylpropionamide (2) and (S)-N-(2-oxo-3-oxetanyl)- biphenyl-4-carboxamide (3) inhibit NAAA, prevent FAE hydrolysis in activated inflammatory cells, and reduce tissue reactions to pro-inflammatory stimuli. Recently, our group disclosed ARN077 (4), a potent NAAA inhibitor that is active in vivo by topical administration in rodent models of hyperalgesia and allodynia. In the present study, we investigated the structure-activity relationship (SAR) of threonine-derived β-lactone analogues of compound 4. The main results of this work were an enhancement of the inhibitory potency of β-lactone carbamate derivatives for NAAA and the identification of (4-phenylphenyl)-methyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]carbamate (14q) as the first single-digit nanomolar inhibitor of intracellular NAAA activity (IC50 = 7 nM on both rat NAAA and human NAAA).

DISUBSTITUTED BETA-LACTONES AS INHIBITORS OF N-ACYLETHANOLAMINE ACID AMIDASE (NAAA)

The present invention provides compounds and pharmaceutical compositions for inhibiting N-acylethanolamine acid amidase (NAAA). Inhibition of NAAA is contemplated as a method to sustain the levels of palmitoylethanolamide (PEA) and oleylethanolamide (OEA), two substrates of NAAA, in conditions characterized by reduced concentrations of PEA and OEA. The invention also provides methods for treating inflammatory diseases and pain, and other disorders in which decreased levels of PEA and OEA are associated with the disorder.