20146-63-8

Usage

Uses

Used in Organic Synthesis:
2-Bromo-4-nitroquinoline is used as a reagent or intermediate for [application reason] in the synthesis of various organic compounds. Its unique structure and functional groups allow for versatile reactions and transformations, making it a valuable component in the development of new molecules and materials.
Used in Pharmaceutical Industry:
2-Bromo-4-nitroquinoline is used as a building block for [application reason] in the design and synthesis of potential pharmaceutical compounds. Its presence in the quinoline family suggests that it may have potential applications in the development of new drugs, particularly those targeting specific biological pathways or receptors.
Used in Chemical Research:
2-Bromo-4-nitroquinoline is used as a research tool for [application reason] in the study of chemical reactions and mechanisms. Its distinct structure and reactivity provide insights into the behavior of organobromides and nitrocompounds, contributing to the broader understanding of chemical processes and interactions.

InChI:InChI=1/C9H5BrN2O2/c10-9-5-8(12(13)14)6-3-1-2-4-7(6)11-9/h1-5H

Upstream product

• 56-57-5 4-nitroquinoline-N-oxide 
• 7789-60-8 phosphorus tribromide 
• 141-78-6 ethyl acetate 
• 67-66-3 chloroform 

Downstream Products

• 20151-40-0 2,4-dibromoquinoline 
• 36825-35-1 2-bromoquinolin-4-ylamine 
• 1246093-98-0 tert-butyl methyl(4-(4-nitroquinolin-2-yl)phenyl)carbamate 
• 1313359-28-2 tert-butyl methyl(4-(4-fluoroquinolin-2-yl)phenyl)carbamate 

Relevant academic research and scientific papers

An Oxygen-peri-Bridged Quinolinium Cation and Its Monoradical Counterpart

Generation of a σ,σ,π-triradical was attempted by collision-activated dissociation (CAD) of two iodine atoms and an NO· radical from 2,4-diiodo-5-nitroquinolinium cation in an ion trap mass spectrometer. However, the reactivity of the product was consistent with a monoradical rather than a triradical. The mechanism of its formation was explored. In the first CAD step, an iodine atom is lost to generate the 2-iodo-5-nitro-4-dehydroquinolinium cation. Quantum chemical calculations suggest that in the second CAD step, the radical site at C-4 adds to the adjacent NO2 group followed by loss of NO· to generate the 2-iodo-4-oxyl-5-dehydroquinolinium cation. Calculations also suggest that in the third CAD step, this cation cyclizes to form an oxygen-peri-bridged 2-iodoquinolinium cation that then loses the remaining iodine atom to generate a distonic 4,5-oxygen-peri-bridged 2-dehydroquinolinium cation. For the analogous 4-oxyl-5-dehydroquinolinium cation, the cyclization is calculated to be exoergic by 8.7 kcal mol–1, with a free energy barrier of 14.0 kcal mol–1. The cyclized product is the first experimentally observed oxygen-peri-bridged naphthalene derivative. It displays low reactivity. However, it's monoradical counterpart is highly reactive and undergoes typical radical reactions.

For detecting imaging agent of neurological disorders

Imaging agents of formulas (I)-(V) and methods for detecting neurological disorders comprising administering to a patient in need compounds of formulas (I)-(V) capable of binding to tau proteins and β-amyloid peptides are presented herein. The invention also relates to methods of imaging Aβ and tau aggregates comprising introducing a detectable quantity of pharmaceutical formulation comprising a radiolabeled compound of formulas (I)-(V) and detecting the labeled compound associated with amyloid deposits and/or tau proteins in a patient. These methods and compositions enable preclinical diagnosis and monitoring progression of AD and other neurological disorders.

Synthesis of 4,5-bis(dimethylamino)quinolines and the dual direction of their protonation

A study on the synthesis of derivatives of 4,5-bis(dimethylamino)quinoline, which is a quinoline analog of 1,8-bis(dimethylamino)naphthalene (also known by its trade name Proton Sponge) was carried out. The first two representatives of this series were obtained. Depending on the aggregate state, solvent, and structural features, these compounds may be protonated either at the quinoline heteroatom or peri-NMe2 groups.

Imaging agents for detecting neurological disorders

Imaging agents of formula (I) and methods for detecting neurological disorders comprising administering to a patient in need compounds of formula (I) capable of binding to tau proteins and β-amyloid peptides are presented herein. The invention also relates to methods of imaging Aβ and tau aggregates comprising introducing a detectable quantity of pharmaceutical formulation comprising a radiolabeled compound of formula (I) and detecting the labeled compound associated with amyloid deposits and/or tau proteins in a patient. These methods and compositions enable preclinical diagnosis and monitoring progression of AD and other neurological disorders.

A3 ADENOSINE RECEPTOR ALLOSTERIC MODULATORS

The present invention provides 2,4-disubstituted quinoline derivatives being an A3 adenosine receptor modulator (A3RM), for use in the treatment of a condition which is treatable by adenosine, an A3 adenosine receptor (A3AR) agonist or an A3 adenosine receptor antagonist. In one embodiment, the 2,4-disubstituted quinoline derivatives are for use in the treatment of a condition treatable by an adenosine or an A3AR agonist, treatment being achieved by enhancing activity of a protein (by binding of said 2,4 disubstituted quinoline derivative to the A3AR). Some conditions treatable by the 2,4 disubstituted quinoline derivative when used for enhancing activity include, malignancy, an immuno-compromised affliction, high intraocular pressure or a condition associated with high intraocular pressure. The invention also provides method for treatment of a subject having a condition treatable by adenosine, an A3AR agonist or an A3AR antagonist making use of the defined 2,4-disubstituted quinoline derivative (s), and pharmaceutical composition and comprising said derivative and a kit comprising the derivative and instructions for use thereof. One specific 2,4-disubstituted quinoline derivative comprises N-{2-[(3,4-dichlorophenyl)amino]quinolin-4-yl}cyclohexanecarboxamide In one embodiment, the 2,4-disubstituted quinoline derivatives in accordance with the invention are formulated in a form suitable for oral administration.

A series of 2,4-disubstituted quinolines as a new class of allosteric enhancers of the adenosine A3 receptor

The adenosine receptor subfamily consists of the adenosine A1, A2A, A2B, and A3 receptors, which are localized in a variety of tissues throughout the human body. It is, therefore, a challenge to develop receptor specific ligands with improved tissue selectivity. Allosteric modulators could have these therapeutic advantages over orthosteric ligands. In the present study, a series of 2,4-disubstituted quinolines were synthesized on the basis of the structure of LUF6000 (34). Compound 27 (LUF6096) was able to allosterically enhance agonist binding to a similar extent as 34. In addition, this new compound showed low, if any, orthosteric affinity for any of the adenosine receptors. In a functional assay, compound 27 showed improved activity in comparison to 34, as it increased both the intrinsic efficacy and the potency of the reference agonist Cl-IB-MECA at the human adenosine A 3 receptor.