849237-14-5

Basic information

• Product Name: 1-Boc-4-(4-cyanobenzyl)piperazine
• Synonyms: 1-Boc-4-(4-cyanobenzyl)piperazine;4-[(4-Cyanophenyl)Methyl]-1-piperazinecarboxylic Acid 1,1-DiMethylethyl Ester;tert-Butyl 4-(4-cyanobenzyl)piperazine-1-carboxylate;1-Boc-4-(4-Cyanobenzyl)
• CAS NO: 849237-14-5
• Molecular Formula: C₁₇H₂₃N₃O₂
• Molecular Weight: 301.388
• EINECS: 604-604-1
• Product Categories: Aromatics
• Mol File: 849237-14-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 117-118°C
• Boiling Point: 423.4°C at 760 mmHg
• Flash Point: 209.8°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 2.25E-07mmHg at 25°C
• Refractive Index: 1.565
• Storage Temp.: 2-8°C
• PKA: 5.63±0.10(Predicted)
• CAS DataBase Reference: 1-Boc-4-(4-cyanobenzyl)piperazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Boc-4-(4-cyanobenzyl)piperazine(849237-14-5)
• EPA Substance Registry System: 1-Boc-4-(4-cyanobenzyl)piperazine(849237-14-5)

Safety Data

• Hazardous Substances Data: 849237-14-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

InChI:InChI=1/C17H23N3O2/c1-17(2,3)22-16(21)20-10-8-19(9-11-20)13-15-6-4-14(12-18)5-7-15/h4-7H,8-11,13H2,1-3H3

Upstream product

• 56553-60-7 sodium tris(acetoxy)borohydride 
• 105-07-7 4-cyanobenzaldehyde 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 17201-43-3 4-cyanobenzyl bromide 

Downstream Products

• 1314143-43-5 4-((4-(L-phenylalanyl)piperazin-1-yl)methyl)benzonitrile 
• 1314143-49-1 4-((4-((4-(4-acetylpiperazin-1-yl)benzyl)-L-phenylalanyl)piperazin-1-yl)methyl)benzonitrile 
• 1314143-38-8 tert-butyl (S)-(1-(4-(4-cyanobenzyl)piperazin-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 1158548-82-3 4-[(piperazin-1-yl)methyl]benzonitrile dihydrochloride 
• 1415109-59-9 4-(4-aminomethylbenzyl)piperazine-1-carboxylic acid tert-butyl ester 
• 89292-70-6 4-(piperazin-1-ylmethyl)benzonitrile 

Relevant articles and documents

Novel indirect AMP-activated protein kinase activators: Identification of a second-generation clinical candidate with improved physicochemical properties and reduced hERG inhibitory activity

This study reports the synthesis and evaluation of novel indirect AMP-activated protein kinase (AMPK) activators. The series of compounds selectively inhibited cell growth in several human breast cancer cell lines by activating AMPK. We performed back-up medicinal chemistry synthetic research on ASP4132, a previously reported as a compound for clinical development that acts as an indirect AMPK activator. This led to the successful identification of 4-({4-[5-({1-[(5-ethoxypyrazin-2-yl)methyl]-4-fluoropiperidin-4-yl}methoxy)-3-methylpyridine-2-carbonyl]piperazin-1-yl}methyl)benzonitrile succinate (27b), a potent, highly aqueous soluble and metabolically stable compound in human hepatocytes. Compound 27b also showed weaker human Ether-a-go-go Related Gene (hERG) inhibitory activity than that of compound 13 and ASP4132. Therefore, 27b was a promising AMPK activator and a second-generation clinical candidate for treatment for human cancer.

Discovery and Characterization of ACT-451840: an Antimalarial Drug with a Novel Mechanism of Action

More than 40 % of the world's population is at risk of being infected with malaria. Most malaria cases occur in the countries of sub-Saharan Africa, Central and South America, and Asia. Resistance to standard therapy, including artemisinin combinations, is increasing. There is an urgent need for novel antimalarials with new mechanisms of action. In a phenotypic screen, we identified a series of phenylalanine-based compounds that exhibit antimalarial activity via a new and yet unknown mechanism of action. Our optimization efforts culminated in the selection of ACT-451840 [(S,E)-N-(4-(4-acetylpiperazin-1-yl)benzyl)-3-(4-(tert-butyl)phenyl)-N-(1-(4-(4-cyanobenzyl)piperazin-1-yl)-1-oxo-3-phenylpropan-2-yl)acrylamide] for clinical development. Herein we describe our optimization efforts from the screening hit to the potential drug candidate with respect to antiparasitic activity, drug metabolism and pharmacokinetics (DMPK) properties, and in vivo pharmacological efficacy.