479353-63-4

Basic information

• Product Name: 4-(4-CARBOXYBENZYL)PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• Synonyms: 4-(4-N-Boc-Piperazin-1-yl)methylbenzoic acid;1-Boc-4-(4-carboxybenzyl)piperazine;1-(4-carboxyphenylMethyl)-4-Boc piperazine;4-(4-Carboxybenzyl)piperazine, N1-BOC protected, tert-Butyl 4-(4-carboxybenzyl)piperazine-1-carboxylate;4-[(4-Boc-piperazin-1-yl)Methyl]benzoic acid;1-Boc-4-(4-Carboxybenzyl);BUTTPARK 99\06-03;4-(PIPERAZIN-1-YL)METHYLBENZOIC ACID, N4-BOC PROTECTED
• CAS NO: 479353-63-4
• Molecular Formula: C₁₇H₂₄N₂O₄
• Molecular Weight: 320.38
• Product Categories: Carboxylic Acids;Phenyls & Phenyl-Het;Carboxylic Acids;Phenyls & Phenyl-Het
• Mol File: 479353-63-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 196 °C
• Boiling Point: 452.6 ºC at 760 mmHg
• Flash Point: 227.5ºC
• Appearance: /
• Density: 1.201±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 5.57E-09mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: 2-8°C
• PKA: 4.02±0.10(Predicted)
• CAS DataBase Reference: 4-(4-CARBOXYBENZYL)PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-CARBOXYBENZYL)PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(479353-63-4)
• EPA Substance Registry System: 4-(4-CARBOXYBENZYL)PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(479353-63-4)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 479353-63-4(Hazardous Substances Data)

Usage

General Description

4-(4-Carboxybenzyl)piperazine-1-carboxylic acid tert-butyl ester is a chemical compound with the molecular formula C20H26N2O4. It is a piperazine derivative with a tert-butyl ester group. 4-(4-CARBOXYBENZYL)PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is often used as a building block in the synthesis of potential pharmaceutical drugs or in medicinal chemistry research. It has been studied for its potential as a neurotransmitter modulator and has also been investigated for its potential anti-cancer properties. Additionally, it has been used in the development of certain chemical reagents and as an intermediate in organic synthesis.

InChI:InChI=1/C17H24N2O4/c1-17(2,3)23-16(22)19-10-8-18(9-11-19)12-13-4-6-14(7-5-13)15(20)21/h4-7H,8-12H2,1-3H3,(H,20,21)

Upstream product

• 1642-81-5 p-(chloromethyl)benzoic acid 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 844891-11-8 tert-butyl 4-[(4-methoxycarbonylphenyl)methyl]piperazine-1-carboxylate 
• 1571-08-0 methyl 4-formylbenzoate 

Downstream Products

• 1414935-22-0 4-[4-(4-carbamoyl-2-pyridin-4-yl-thiazol-5-ylcarbamoyl)-benzyl]-piperazine-1-carboxylic acid tert-butyl ester 
• 404844-02-6 N-Desmethyl Imatinib 
• 1076199-23-9 tert-butyl 4-(4-((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)carbamoyl)benzyl)piperazine-1-carboxylate 
• 1344034-11-2 tert-butyl 4-(4-(2-(2-(propylamino)pyridin-4-yl)-1H-benzo[d]imidazol-4-ylcarbamoyl)benzyl)piperazine-1-carboxylate 
• 1344034-06-5 tert-butyl 4-(4-(2-(2-chloropyridin-4-yl)-1H-benzo[d]imidazol-4-ylcarbamoyl)benzyl)piperazine-1-carboxylate 

Relevant articles and documents

Synthesis, in vitro and in vivo evaluation of 18F-fluoronorimatinib as radiotracer for Imatinib-sensitive gastrointestinal stromal tumors

Introduction Gastrointestinal stromal tumors (GIST) have a wide range of mutations, but can mostly be treated with Imatinib, until eventually resistance towards this tyrosine kinase inhibitor is acquired. Early and non-invasive determination of the sensitivity of the tumor and its metastases towards Imatinib by positron emission tomography (PET) would be beneficial for therapy planning and monitoring. Methods We developed a synthesis strategy towards the precursor molecule, performed the 18F-synthesis and in the following evaluated the radioligand in vitro regarding its lipophilicity, stability and biological activity (KIT binding properties) as well as its in vivo properties in GIST tumor-bearing mice. Results [18F]fluoronorimatinib could be obtained in an overall radiochemical yield of 22.2 ± 3.3% within 90 min. The radioligand showed high GIST cell uptake and was able to distinguish between Imatinib-sensitive and resistant tumor cell lines (GIST-T1, GIST882, GIST430) in vitro. Further biological evaluations of the ligand towards 9 different GIST-relevant KIT mutations showed comparable binding affinities compared to the structural lead Norimatinib (65 nM vs. 53 nM for wt-KIT). The in vivo evaluation of the newly developed radioligand showed tumor-to-background-ratios comparable to previously described, similar radiotracers. Conclusions Thus, [18F]fluoronorimatinib is able to distinguish between Imatinib-resistant and sensitive KIT mutations. Although no improvement of in vivo tumor-to-background ratios could be achieved compared to formerly described radioligands, the hepatic uptake could be considerably reduced, being advantageous for the imaging of GIST. Advances in knowledge and implications for patient care: We were able to show that it is possible to significantly reduce the unfavorably high hepatic uptake of small-molecule radioligands applicable for GIST PET imaging. This work can thus be the basis for further work intending to develop a PET-radioligand for Imatinib-dependent GIST imaging.

COMPOSITIONS AND METHODS FOR INHIBITING KINASES

The present invention provides compounds for the prevention or treatment of cancer or a bacterial or viral infection. Additionally, the present invention provides compositions and methods for using these compounds and compositions in the prevention or treatment of cancer or a bacterial or viral infection in a subject.