36825-35-1

Usage

Uses

Used in Organic Synthesis:
4-Amino-2-bromoquinoline is used as an intermediate in the synthesis of other complex organic compounds. Its unique structure with an amino group and a bromine atom allows for various chemical reactions and modifications, making it a valuable building block in the creation of new molecules with potential applications in various fields.
Used in Pharmaceutical Industry:
4-Amino-2-bromoquinoline is used as a starting material for the development of new pharmaceutical compounds. Its structural features can be exploited to design drugs with specific therapeutic properties, such as antimicrobial, anticancer, or anti-inflammatory agents. The versatility of the quinoline ring system in 4-AMINO-2-BROMOQUINOLINE enables the synthesis of a wide range of bioactive molecules.
Used in Chemical Research:
4-Amino-2-bromoquinoline is used as a research tool in the field of chemistry, particularly in the study of quinoline-based compounds and their properties. It can be employed to investigate the reactivity, stability, and other characteristics of quinoline derivatives, contributing to the understanding of their potential applications and limitations.
Used in Material Science:
4-Amino-2-bromoquinoline can be used as a component in the development of new materials with specific properties, such as electronic, optical, or catalytic functions. The presence of the amino and bromine groups in the quinoline ring system can influence the electronic properties of the resulting materials, making them suitable for various applications in material science.

InChI:InChI=1/C9H7BrN2/c10-9-5-7(11)6-3-1-2-4-8(6)12-9/h1-5H,(H2,11,12)

Upstream product

• 20151-40-0 2,4-dibromoquinoline 
• 20146-63-8 2-bromo-4-nitroquinoline 

Relevant academic research and scientific papers

Design, synthesis, and structure-activity relationships of highly potent 5-HT3 receptor ligands

The 5-HT3 receptor, a pentameric ligand-gated ion channel (pLGIC), is an important therapeutic target. During a recent fragment screen, 6-chloro-N-methyl-2-(4-methyl-1,4-diazepan-1-yl)quinazolin-4-amine (1) was identified as a 5-HT3R hit fragment. Here we describe the synthesis and structure-activity relationships (SAR) of a series of (iso)quinoline and quinazoline compounds that were synthesized and screened for 5-HT3R affinity using a [3H]granisetron displacement assay. These studies resulted in the discovery of several high affinity ligands of which compound 22 showed the highest affinity (pKi > 10) for the 5-HT3 receptor. The observed SAR is in agreement with established pharmacophore models for 5-HT3 ligands and is used for ligand-receptor binding mode prediction using homology modeling and in silico docking approaches.

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.

Multiple regioselective functionalizations of quinolines via magnesiations

A wide range of polyfunctionalized quinolines was prepared via chemo- and regioselective magnesiation reactions using appropriate Mg reagents, such as i-PrMgCl-LiCl, MesMgBr·LiCl, Mes2Mg·2LiBr, TMPMgCl·LiCl, and TMP2Mg·2LiCl. An application to the total synthesis of the biologically active compound talnetant was performed (six steps, 28%).