1403029-48-0

Basic information

• Product Name: 2-2-chlorophenylethylcarbamic acid methyl ester
• Synonyms: 2-2-chlorophenylethylcarbamic acid methyl ester
• CAS NO: 1403029-48-0
• Molecular Weight: 213.664
• Mol File: 1403029-48-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-2-chlorophenylethylcarbamic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-2-chlorophenylethylcarbamic acid methyl ester(1403029-48-0)
• EPA Substance Registry System: 2-2-chlorophenylethylcarbamic acid methyl ester(1403029-48-0)

Safety Data

• Hazardous Substances Data: 1403029-48-0(Hazardous Substances Data)

Upstream product

• 13078-80-3 2-(2-chlorophenyl)ethanamine 
• 79-22-1 methyl chloroformate 

Downstream Products

• 52516-17-3 2-(2-chlorochlorophenyl)-N-methylethanamine 

Relevant articles and documents

Structure-Activity Relationship Studies of Pyrimidine-4-Carboxamides as Inhibitors of N-Acylphosphatidylethanolamine Phospholipase D

N-Acylphosphatidylethanolamine phospholipase D (NAPE-PLD) is regarded as the main enzyme responsible for the biosynthesis of N-acylethanolamines (NAEs), a family of bioactive lipid mediators. Previously, we reported N-(cyclopropylmethyl)-6-((S)-3-hydroxypyrrolidin-1-yl)-2-((S)-3-phenylpiperidin-1-yl)pyrimidine-4-carboxamide (1, LEI-401) as the first potent and selective NAPE-PLD inhibitor that decreased NAEs in the brains of freely moving mice and modulated emotional behavior [ Mock et al. Nat Chem. Biol., 2020, 16, 667-675 ]. Here, we describe the structure-activity relationship (SAR) of a library of pyrimidine-4-carboxamides as inhibitors of NAPE-PLD that led to the identification of LEI-401. A high-throughput screening hit was modified at three different substituents to optimize its potency and lipophilicity. Conformational restriction of an N-methylphenethylamine group by replacement with an (S)-3-phenylpiperidine increased the inhibitory potency 3-fold. Exchange of a morpholine substituent for an (S)-3-hydroxypyrrolidine reduced the lipophilicity and further increased activity by 10-fold, affording LEI-401 as a nanomolar potent inhibitor with drug-like properties. LEI-401 is a suitable pharmacological tool compound to investigate NAPE-PLD function in vitro and in vivo.

INHIBITORS OF N-ACYLPHOSPHATIDYLETHANOLAMINE PHOSPHOLIPASE D (NAPE-PLD)

The invention relates to a compound of the formula (I) as novel inhibitor of N-acylphosphatidylethanolamine phospholipase D (NAPE-PLD), and to use thereof for the prophylaxis or treatment of diseases associated with NAPE-PLD. wherein in a ring A, X1 is N, or CR4; X2 is N or CR5; X3 is N or CH; with the proviso that at least one of X1 and X3 is N.