1257300-31-4

Basic information

• Product Name: 1-Benzyl 4-(tert-butyl) 2-phenylpiperazine-1,4-dicarboxylate
• Synonyms: 1-Benzyl 4-(tert-butyl) 2-phenylpiperazine-1,4-dicarboxylate
• CAS NO: 1257300-31-4
• Molecular Weight: 396.486
• Mol File: 1257300-31-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-Benzyl 4-(tert-butyl) 2-phenylpiperazine-1,4-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzyl 4-(tert-butyl) 2-phenylpiperazine-1,4-dicarboxylate(1257300-31-4)
• EPA Substance Registry System: 1-Benzyl 4-(tert-butyl) 2-phenylpiperazine-1,4-dicarboxylate(1257300-31-4)

Safety Data

• Hazardous Substances Data: 1257300-31-4(Hazardous Substances Data)

Upstream product

• 502649-25-4 tert-butyl 4-(3-methoxy-4-(1H-pyrazol-4-yl)benzoyl)-3-phenylpiperazine-1-carboxylate 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 912763-14-5 benzyl 2-phenylpiperazine-1-carboxylate 
• 1257300-33-6 1,3-diphenylpiperazine 
• 1257300-32-5 benzyl 2,4-diphenylpiperazine-1-carboxylate 

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.

BENZOXAZEPINES AS INHIBITORS OF P13K/MTOR AND METHODS OF THEIR USE AND MANUFACTURE

The invention is directed to Compounds of Formula I: and pharmaceutically acceptable salts or solvates thereof, as well as methods of making and using the compounds. 9936396.1