76228-06-3

Basic information

• Product Name: 6-Bromo-2,3-Dihydroquinolin-4(1H)-One
• Synonyms: 6-Bromo-2,3-Dihydroquinolin-4(1H)-One;6-broMo-1,2,3,4-tetrahydroquinolin-4-one;6-Bromo-2,3-dihydro-1H-quinolin-4-one;6-Bromo-2,3-dihydroquinolin-4(1H)
• CAS NO: 76228-06-3
• Molecular Formula: C₉H₈BrNO
• Molecular Weight: 226.06992
• Mol File: 76228-06-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 225-228 °C(Solv: chloroform (67-66-3); ethyl ether (60-29-7))
• Boiling Point: 359.1 °C at 760 mmHg
• Flash Point: 171 °C
• Appearance: /
• Density: 1.559 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 1.72±0.20(Predicted)
• CAS DataBase Reference: 6-Bromo-2,3-Dihydroquinolin-4(1H)-One(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromo-2,3-Dihydroquinolin-4(1H)-One(76228-06-3)
• EPA Substance Registry System: 6-Bromo-2,3-Dihydroquinolin-4(1H)-One(76228-06-3)

Safety Data

• Hazardous Substances Data: 76228-06-3(Hazardous Substances Data)

Usage

General Description

6-Bromo-2,3-Dihydroquinolin-4(1H)-One is a chemical compound with the molecular formula C9H8BrNO and a molar mass of 223.07 g/mol. It is a derivative of quinolinone and contains a bromine atom at the 6th position of the quinoline ring. 6-Bromo-2,3-Dihydroquinolin-4(1H)-One has been studied for its potential pharmaceutical and biological activities. It is also used as a building block in the synthesis of other organic compounds. 6-Bromo-2,3-Dihydroquinolin-4(1H)-One is a yellow solid at room temperature and should be handled with care due to its potential health hazards.

Upstream product

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Downstream Products

• 1431552-21-4 C₁₀H₁₁BrN₄S 

Relevant articles and documents

NOVEL SUBSTITUTED TETRAHYDROQUINOLIN COMPOUNDS AS INDOLEAMINE 2,3-DIOXYGENASE (IDO) INHIBITORS

Disclosed herein is a compound of formula (I), or a pharmaceutically acceptable salt thereof (I). Also disclosed herein are uses of the compounds disclosed herein in the potential treatment or prevention of an IDO-associated disease or disorder. Also disclosed herein are compositions comprising a compound disclosed herein. Further disclosed herein are uses of the compositions in the potential treatment or prevention of an IDO-associated disease or disorder.

Further Optimization and Evaluation of Bioavailable, Mixed-Efficacy μ-Opioid Receptor (MOR) Agonists/δ-Opioid Receptor (DOR) Antagonists: Balancing MOR and DOR Affinities

In a previously described peptidomimetic series, we reported the development of bifunctional δ-opioid receptor (MOR) agonist and δ-opioid receptor (DOR) antagonist ligands with a lead compound that produced antinociception for 1 h after intraperitoneal administration in mice. In this paper, we expand on our original series by presenting two modifications, both of which were designed with the following objectives: (1) probing bioavailability and improving metabolic stability, (2) balancing affinities between MOR and DOR while reducing affinity and efficacy at the δ-opioid receptor (KOR), and (3) improving in vivo efficacy. Here, we establish that, through N-acetylation of our original peptidomimetic series, we are able to improve DOR affinity and increase selectivity relative to KOR while maintaining the desired MOR agonist/DOR antagonist profile. From initial in vivo studies, one compound (14a) was found to produce dose-dependent antinociception after peripheral administration with an improved duration of action of longer than 3 h.

Small-molecule inhibitors of cathepsin L incorporating functionalized ring-fused molecular frameworks

Cathepsin L is a cysteine protease that is upregulated in a variety of malignant tumors and plays a significant role in cancer cell invasion and migration. It is an attractive target for the development of small-molecule inhibitors, which may prove beneficial as treatment agents to limit or arrest cancer metastasis. We have previously identified a structurally diverse series of thiosemicarbazone-based inhibitors that incorporate the benzophenone and thiochromanone molecular scaffolds. Herein we report an important extension of this work designed to explore fused aryl-alkyl ring molecular systems that feature nitrogen atom incorporation (dihydroquinoline-based) and carbon atom exclusivity (tetrahydronaphthalene-based). In addition, analogues that contain oxygen (chromanone-based), sulfur (thiochroman-based), sulfoxide, and sulfone functionalization have been prepared in order to further investigate the structure-activity relationship aspects associated with these compounds and their ability to inhibit cathepsins L and B. From this small-library of 30 compounds, five were found to be strongly inhibitory (IC50 50 = 164 nM. All of the compounds evaluated were inactive (IC50 >10,000 nM) as inhibitors of cathepsin B, thus establishing a high degree (>20-fold) of selectivity (cathepsin L vs. cathepsin B) for the most active cathepsin L inhibitors in this series.