939757-97-8

Basic information

• Product Name: 4-(4-BROMO-PHENYL)-PYRROLIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
• Synonyms: 4-(4-BROMO-PHENYL)-PYRROLIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER;1-BOC-4-(4-BROMO-PHENYL)-PYRROLIDINE-3-CARBOXYLIC ACID;4-(4-bromophenyl)-1-Boc-pyrrolidine-3-carboxylic acid;4-(4-Bromophenyl)-1-(tert-butoxycarbonyl)-3-pyrrolidinecarboxylic acid
• CAS NO: 939757-97-8
• Molecular Formula: C16H20BrNO4
• Molecular Weight: 370.2383
• Mol File: 939757-97-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 478.5°C at 760 mmHg
• Flash Point: 243.2°C
• Appearance: /
• Density: 1.426g/cm³
• Vapor Pressure: 5.77E-10mmHg at 25°C
• Refractive Index: 1.569
• CAS DataBase Reference: 4-(4-BROMO-PHENYL)-PYRROLIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-BROMO-PHENYL)-PYRROLIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER(939757-97-8)
• EPA Substance Registry System: 4-(4-BROMO-PHENYL)-PYRROLIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER(939757-97-8)

Safety Data

• Hazardous Substances Data: 939757-97-8(Hazardous Substances Data)

Usage

General Description

4-(4-Bromo-phenyl)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester is a chemical compound with a molecular formula C17H20BrNO4. It is a white crystalline powder that is commonly used in organic synthesis and pharmaceutical research. 4-(4-BROMO-PHENYL)-PYRROLIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER is classified as a pyrrolidine carboxylic acid derivative and is often used as a building block in the synthesis of various pharmaceutical and agrochemical products. It has the potential to act as a GABA receptor agonist, making it of interest for research into potential therapeutic applications. Additionally, its tert-butyl ester group provides stability and protection during chemical reactions, making it a versatile and useful compound in organic chemistry.

InChI:InChI=1/C16H20BrNO4/c1-16(2,3)22-15(21)18-8-12(13(9-18)14(19)20)10-4-6-11(17)7-5-10/h4-7,12-13H,8-9H2,1-3H3,(H,19,20)

Upstream product

• 24393-53-1 ethyl (E)-3-(4-bromophenyl)-2-propenoate 
• 24424-99-5 di-tert-butyl dicarbonate 

Relevant articles and documents

Pharmacokinetic optimization of class-selective histone deacetylase inhibitors and identification of associated candidate predictive biomarkers of hepatocellular carcinoma tumor response

Herein, we describe the pharmacokinetic optimization of a series of class-selective histone deacetylase (HDAC) inhibitors and the subsequent identification of candidate predictive biomarkers of hepatocellular carcinoma (HCC) tumor response for our clinical lead using patient-derived HCC tumor xenograft models. Through a combination of conformational constraint and scaffold hopping, we lowered the in vivo clearance (CL) and significantly improved the bioavailability (F) and exposure (AUC) of our HDAC inhibitors while maintaining selectivity toward the class I HDAC family with particular potency against HDAC1, resulting in clinical lead 5 (HDAC1 IC50 = 60 nM, mouse CL = 39 mL/min/kg, mouse F = 100%, mouse AUC after single oral dose at 10 mg/kg = 6316 h·ng/mL). We then evaluated 5 in a biomarker discovery pilot study using patient-derived tumor xenograft models, wherein two out of the three models responded to treatment. By comparing tumor response status to compound tumor exposure, induction of acetylated histone H3, candidate gene expression changes, and promoter DNA methylation status from all three models at various time points, we identified preliminary candidate response prediction biomarkers that warrant further validation in a larger cohort of patient-derived tumor models and through confirmatory functional studies.