258515-65-0

Basic information

• Product Name: TERT-BUTYL 7-BROMO-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE
• Synonyms: TERT-BUTYL 7-BROMO-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE;N-Boc-7-BroMo-1,2,3,4-Tetrahydroisoquinoline;7-BroMo-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester;2-Boc-7-bromo-3,4-dihydro-1H-isoquinoline;tert-butyl 7-bromo-1,2,3,4-tetrahydroisoquinoline-2-carboxylate
• CAS NO: 258515-65-0
• Molecular Formula: C₁₄H₁₈BrNO₂
• Molecular Weight: 312.20222
• Mol File: 258515-65-0.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 374.2 °C at 760 mmHg
• Flash Point: 180.1 °C
• Appearance: /
• Density: 1.353 g/cm³
• Vapor Pressure: 8.48E-06mmHg at 25°C
• Refractive Index: 1.559
• Storage Temp.: 2-8°C
• PKA: -1.55±0.20(Predicted)
• CAS DataBase Reference: TERT-BUTYL 7-BROMO-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 7-BROMO-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE(258515-65-0)
• EPA Substance Registry System: TERT-BUTYL 7-BROMO-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE(258515-65-0)

Safety Data

• Hazardous Substances Data: 258515-65-0(Hazardous Substances Data)

Usage

General Description

Tert-butyl 7-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate is a chemical compound with a molecular formula of C15H19BrNO2. It is a derivative of isoquinoline, which is a heterocyclic compound commonly found in some natural products, drugs, and other biologically active molecules. This specific compound is a tert-butyl ester derivative, which means it contains a tert-butyl group attached to the carboxylate functional group. The bromine atom is located at the 7-position of the isoquinoline ring, and the compound is in a dihydroisoquinoline form. This chemical structure may have potential applications in pharmaceuticals, organic synthesis, and other chemical processes.

InChI:InChI=1/C14H18BrNO2/c1-14(2,3)18-13(17)16-7-6-10-4-5-12(15)8-11(10)9-16/h4-5,8H,6-7,9H2,1-3H3

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 220247-73-4 7-bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride 
• 17680-55-6 7-bromo-1,2,3,4-tetrahydroisoquinoline 
• 24608-52-4 tert-butyl chloroformate 
• 135335-11-4 ethyl <2-(4-bromophenyl)ethyl>carbamate 
• 73918-56-6 4-Bromophenethylamine 
• 16532-79-9 4-Bromophenylacetonitrile 

Downstream Products

• 1008517-78-9 7-[2-(toluene-4-sulfonyloxy)-ethyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 1184950-44-4 7-[1,1-difluoro-2-(toluene-4-sulfonyloxy)-ethyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 149353-95-7 2-[(tert-butoxy)carbonyl]-1 ,2,3,4-tetrahydroisoquinoline-7-carboxylic acid 
• 1190058-21-9 {2-[(tert-butoxy)carbonyl]-1,2,3,4-tetrahydroisoquinolin-7-yl}boronic acid 

Relevant articles and documents

Structure-activity relationships of 7-substituted dimethyltyrosine-tetrahydroisoquinoline opioid peptidomimetics

The opioid receptors modulate a variety of biological functions, including pain, mood, and reward. As a result, opioid ligands are being explored as potential therapeutics for a variety of indications. Multifunctional opioid ligands, which act simultaneously at more than one type of opioid receptor, show promise for use in the treatment of addiction, pain, and other conditions. Previously, we reported the creation of bifunctional kappa opioid receptor (KOR) agonist/mu opioid receptor (MOR) partial agonist ligands from the classically delta opioid receptor (DOR) antagonist selective dimethyltyrosine-tetrahydroisoquinoline (Dmt-Tiq) scaffold through the addition of a 7-benzyl pendant on the tetrahydroisoquinoline ring. This study further explores the structure-activity relationships surrounding 7-position pendants on the Dmt-Tiq scaffold. Some analogues maintain a KOR agonist/MOR partial agonist profile, which is being explored in the development of a treatment for cocaine addiction. Others display a MOR agonist/DOR antagonist profile, which has potential to be used in the creation of a less addictive pain medication. Ultimately, we report the synthesis and in vitro evaluation of novel opioid ligands with a variety of multifunctional profiles.

MACROCYCLIC COMPOUND AND USE THEREOF

A compound represented by the following formula (I): wherein each symbol in the formula is as described herein or a salt thereof has an NRF2 activating activity, and is expected to be useful as a preventive or therapeutic agent for diseases associated with oxidative stress, in particular, hepatic disease (for example, non-alcoholic steatohepatitis (NASH)), cardiovascular disease (for example, heart failure or pulmonary arterial hypertension), lung disease (for example, chronic obstructive pulmonary disease (COPD)), kidney disease (for example, chronic kidney disease (CKD) or acute kidney injury (AKI)), central nervous system disease (for example, Parkinson's disease), mitochondrial disease (for example, Friedreich motor ataxia, mitochondrial myopathy), inflammatory disease (for example, multiple sclerosis (MS), inflammatory bowel disease (IBD)), sickle cell disease, cancer, or the like.

Design, synthesis and biological evaluation of a series of novel GPR40 agonists containing nitrogen heterocyclic rings

A novel series of GPR40 agonists is designed by introducing nitrogen-containing heterocyclic ring at the terminal phenyl ring of TAK-875 with the aim of decreasing its lipophilicity. Three different β-substituted phenylpropionic acids were investigated as the acidic components. A total of 34 compounds have been synthesized, among which, compound 30 exhibited comparable GPR40 agonistic activity in vitro with TAK-875 and relatively lower lipophilicity through calculation (30, EC50 = 1.2 μM, cLogP = 1.3; TAK-875: EC50 = 5.1 μM, cLogP = 3.4). Moreover, compound 30 was able to enhance the insulin secretion of primary islets isolated from normal ICR mice and showed no obvious inhibition against cytochromes P450 in vitro. In vivo, compound 30 exhibited efficacy in oral glucose tolerance test (oGTT) in normal ICR mice.