38171-31-2

Usage

Uses

N-Methyl-4-chlorophenethylamine is a useful reactant for organic reactions and synthesis.

InChI:InChI=1/C9H12ClN/c1-11-7-6-8-2-4-9(10)5-3-8/h2-5,11H,6-7H2,1H3

Upstream product

• 60336-41-6 2-(4-chlorophenyl)-N-methylacetamide 
• 328281-40-9 2-4-chlorophenylethylcarbamic acid methyl ester 
• 167886-56-8 1-[2-(tert-butoxycarbonylamino)ethyl]4-chlorobenzene 

Downstream Products

• 1103521-25-0 2-chloro-N-[2-(4-chlorophenyl)ethyl]-6,7-dimethoxy-N-methylquinazolin-4-amine 
• 1226103-88-3 2-chloro-N-[2-(4-chlorophenyl)ethyl]-N-methylacetamide 
• 1431697-94-7 (±)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride 

Relevant academic research and scientific papers

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.

Efficient Approaches for the Synthesis of Diverse α-Diazo Amides

Metal-catalysed carbenoid chemistry can be exploited for the synthesis of diverse ranges of small molecules from α-diazo carbonyl compounds. In this paper, three synthetic approaches to α-diazo amides are described, and their scope and limitations are determined. On the basis of these synthetic studies, recommendations are provided to assist the selection of the most appropriate approach for specific classes of product. The availability of practical and efficient syntheses of diverse α-diazo acetamides is expected to facilitate the discovery of many different classes of bioactive small molecules.

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.

PROCESS FOR THE ENANTIOSELECTIVE SYNTHESIS OF A TETRAHYDROBENZAZEPINE COMPOUND

This invention relates to an improved process for the enantioselective synthesis of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Structure-activity correlations for β-phenethylamines at human trace amine receptor 1

A cell line in which RD-HGA16 cells were stably transfected with the hTAAR 1 receptor was created and utilized to carry out a systematic evaluation of a series of β-phenethylamines. Fair agreement was observed with data obtained for aryl and ethylene chain substituted analogs in an AV12-664 cell line in which hemagglutinin-tagged hTAAR 1 was stably co-expressed with rat Gαs. Analogs with multiple substituents as well as analogs with bulky groups were found to be partial agonists. Analogs in which the primary amino group was converted to a secondary or a tertiary amino group by N-methylation were also partial agonists. Comparative Molecular Field Analysis (CoMFA) using the potency data yielded a regression coefficient r2 of 0.824. The steric field contribution to the model was 61% with the balance (39%) contributed by the electrostatic field. The collective results suggest that increasing steric bulk both at the amino nitrogen, particularly by N-dimethylation, and at the 4-position of the aromatic ring leads to low efficacy ligands.

Substituted 7,12-methano dibenzazocines and 8,13-methano dibenzazonines

Substituted 7,12-methano-dibenzazocines and 8,13-methanodibenzazonines, e.g., 7,12-dihydro-6,13-dimethyl-7,12-methano-6H-dibenz [c,f] azocine, are prepared by cyclizing 3-benzylamino or 3-phenethylamino -2-alkyl-indan-1-ols and are useful as anti-inflammatory agents.