76228-06-3

Usage

Uses

Used in Pharmaceutical and Biological Research:
6-Bromo-2,3-Dihydroquinolin-4(1H)-One is used as a research compound for exploring its potential pharmaceutical and biological activities. Its unique structure and properties make it a promising candidate for the development of new drugs and therapies.
Used in Organic Synthesis:
In the field of organic chemistry, 6-Bromo-2,3-Dihydroquinolin-4(1H)-One serves as a valuable building block for the synthesis of other organic compounds. Its presence in various chemical reactions can lead to the creation of novel molecules with diverse applications.
Used in Chemical Production:
6-Bromo-2,3-Dihydroquinolin-4(1H)-One is utilized in the chemical production industry as an intermediate or a precursor in the manufacturing process of various chemical products. Its versatility in chemical reactions contributes to the development of new and innovative products.
Used in Material Science:
6-Bromo-2,3-Dihydroquinolin-4(1H)-One may also find applications in material science, where its unique properties can be harnessed to develop new materials with specific characteristics, such as improved stability, enhanced reactivity, or tailored physical properties.
Used in Environmental Applications:
6-Bromo-2,3-Dihydroquinolin-4(1H)-One could be employed in environmental applications, such as in the development of new methods for pollution control or the remediation of contaminated sites, due to its potential reactivity and ability to interact with other compounds.
Used in Analytical Chemistry:
In analytical chemistry, 6-Bromo-2,3-Dihydroquinolin-4(1H)-One may be used as a reference compound or a standard in various analytical techniques, such as chromatography, spectroscopy, or titration, to ensure accurate measurements and reliable results.

Upstream product

• 875827-47-7 N-(4-bromo-phenyl)-N-(toluene-4-sulfonyl)-β-alanine 
• 7661-25-8 N-(4-bromophenyl)azetidin-2-one 
• 106-40-1 4-bromo-aniline 
• 90561-83-4 3-((4-bromophenyl)amino)propanoic acid 
• 106-37-6 1.4-dibromobenzene 
• 7661-10-1 3-bromo-N-(4-bromophenyl)propanamide 
• 66416-72-6 4-bromo-2-iodoaniline 
• 4295-36-7 2,3-dihydroquinolin-4(1H)-one 
• 76227-94-6 ethyl 3-(4-bromophenylamino)propanoate 

Downstream Products

• 1001004-06-3 C₁₆H₁₅NSO 
• 22190-35-8 6-bromo-1,2,3,4-tetrahydroquinoline 
• 1431552-21-4 C₁₀H₁₁BrN₄S 
• 1445800-21-4 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydroquinolin-4(1H)-one 
• 1445800-29-2 6-(4-oxo-1,2,3,4-tetrahydroquinolin-6-yl)picolinic acid 
• 1135871-00-9 6-(4-(2-(benzothiazol-2-yl)hydrazono)-1,2,3,4-tetrahydroquinolin-6-yl)picolinic acid 

Relevant academic research and scientific papers

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.

Superacid-catalyzed tandem Meyer–Schuster rearrangement/intramolecular hydroamination of o-anilinopropargyl alcohols for the synthesis of 2,3-dihydro-4(1H)-quinolones

A TfOH-catalyzed synthesis of 2,3-dihydro-4(1H)-quinolones from o-anilinopropargyl alcohols was developed. Studies of N-protecting groups and substituents in phenyl rings showed that diverse groups could be applied. By controlling the catalyst loading, o-anilinopropargyl alcohols underwent the expected transformation smoothly to produce N-protected or N-deprotected 2,3-dihydro-4 (1H)-quinolones in good yields. This transformation probably involved a tandem Meyer–Schuster rearrangement/intramolecular hydroamination reaction process.

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.

The discovery of I-BET726 (GSK1324726A), a potent tetrahydroquinoline ApoA1 up-regulator and selective BET bromodomain inhibitor

Through their function as epigenetic readers of the histone code, the BET family of bromodomain-containing proteins regulate expression of multiple genes of therapeutic relevance, including those involved in tumor cell growth and inflammation. BET bromodomain inhibitors have profound antiproliferative and anti-inflammatory effects which translate into efficacy in oncology and inflammation models, and the first compounds have now progressed into clinical trials. The exciting biology of the BETs has led to great interest in the discovery of novel inhibitor classes. Here we describe the identification of a novel tetrahydroquinoline series through up-regulation of apolipoprotein A1 and the optimization into potent compounds active in murine models of septic shock and neuroblastoma. At the molecular level, these effects are produced by inhibition of BET bromodomains. X-ray crystallography reveals the interactions explaining the structure-activity relationships of binding. The resulting lead molecule, I-BET726, represents a new, potent, and selective class of tetrahydroquinoline-based BET inhibitors.

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.

Synthesis of 2,3-dihydro-4(1H)-quinolones and the corresponding 4(1H)-quinolones via low-temperature fries rearrangement of N-arylazetidin-2- ones

N-Arylazetidin-2-ones of the general form 1, which are readily prepared by GoldbergBuchwald-type copper-catalyzed coupling of N-unsubstituted azetidin-2-ones with the relevant aryl halide or using Mitsunobu cyclization processes, undergo smooth Fries-rearrangement in triflic acid at 018°C to give the isomeric 2,3-dihydro-4(1H)-quinolones (2). Dehydrogenation of the latter compounds using 10% Pd on C in 1.0M aqueous sodium hydroxide/propan-2-ol mixtures at ca. 82°C provides the corresponding 4(1H)-quinolones (3).

BENZOTHIAZOLE COMPOUNDS

The present invention relates to benzothiazole compounds that mimic the activity of BH3 only proteins and are capable of binding to and neutralizing pro survival Bcl 2 proteins. The invention also relates to the use of such compounds in the regulation of cell death or cell survival and the treatment and/or prophylaxis of diseases or conditions associated with the deregulation of cell death or cell survival.

2-AMINO- AND 2-THIO-SUBSTITUTED 1,3-DIAMINOPROPANES

Disclosed are compounds of the formula: where variables Q, Z, X, R15, R2, R3, and Rc are defined herein. Compounds disclosed herein are inhibitors of the beta-secretase enzyme and are therefore useful in the treatment of Alzheimer’s disease and other diseases characterized by deposition of A beta peptide in a mammal.

METHODS OF TREATMENT OF AMYLOIDOSIS USING BI-CYCLIC ASPARTYL PROTEASE INHIBITORS

The invention relates to novel compounds and methods of treating diseases, disorders, and conditions associated with amyloidosis. Amyloidosis refers to a collection of diseases, disorders, and conditions associated with abnormal deposition of A-beta protein.

Formation of 2,3-Dihydro-4(1H)-quinolones and Related Compounds via Fries-type Acid-catalysed Rearrangement of 1-Arylazetidin-2-ones

A variety of 1-arylazetidin-2-ones were treated with trifluoroacetic acid under reflux, methanesulphonic acid at 100 deg C, or conc. sulphuric acid to give the corresponding 2,3-dihydro-4(1H)-quinolones via acyl migration and N-CO fission.In the case of 1-(3-substituted phenyl)azetidin-2-ones, two positional isomeric products, 5- and 7-substituted 2,3-dihydro-4(1H)-quinolones were obtained. 4-Methyl, 4-ethoxycarbonyl, and 4-piperidin-2-yl-1-arylazetidin-2-ones and their analogues were also converted into the corresponding 2-substituted 2,3-dihydro-4(1H)-quinolones under acidic conditions.The 3-substituted 1-phenylazetidin-2-ones (36) and (37) were converted into the furoquinoline systems (38) and (40), respectively, by application of this method.