80947-25-7

Usage

Uses

Used in Pharmaceutical Industry:
4-AMINO-2-CHLOROQUINOLINE is used as an intermediate in the synthesis of antimalarial drugs for its potent antimalarial activity, contributing to the development of effective treatments against malaria.
Used in Organic Chemistry:
4-AMINO-2-CHLOROQUINOLINE is used as a precursor in various organic chemistry reactions, facilitating the creation of a range of chemical compounds and products.
Used in Fluorescent Dyes Synthesis:
4-AMINO-2-CHLOROQUINOLINE is used as a building block in the synthesis of fluorescent dyes, enabling the production of specialized dyes for various applications, including research and diagnostic tools.

InChI:InChI=1/C9H7ClN2/c10-9-5-7(11)6-3-1-2-4-8(6)12-9/h1-5H,(H2,11,12)

Upstream product

• 2508-86-3 4-aminoquinoline 1-oxide 
• 4295-16-3 2-chloroquinoline-4-carboxamide 
• 703-61-7 2,4-dichloroquinoline 
• 157027-30-0 4-azido-2-chloro-quinoline 
• 2388-32-1 2-chloroquinoline-4-carbonyl chloride 
• 15733-89-8 2-hydroxyquinoline-4-carboxylic acid 
• 1010-61-3 N-(1-oxy-[4]quinolyl)-hydroxylamine; hydrochloride 

Downstream Products

• 1116652-03-9 N-(2-chloroquinolin-4-yl)benzamide 
• 1116652-02-8 N-(2-chloroquinolin-4-yl)cyclohexanecarboxamide 
• 1245211-31-7 C₂₀H₁₄ClN₅O 
• 1245211-33-9 C₂₁H₁₆ClN₅O₂ 
• 1245211-22-6 C₁₇H₁₃Cl₂N₃O₂ 

Relevant academic research and scientific papers

Efficient synthesis, fluorescence and DFT studies of different substituted 2-chloroquinoline-4-amines and benzo[g][1,8]naphthyridine derivatives

An efficient and single step strategy for synthesizing new functionalized benzo[b][1,8]naphthyridine derivatives is presented. Benzo[g][1,8]naphthyridines have been synthesized by the condensation of substituted 2-chloroquinoline-3-carbaldehydes with various 2-chloroquinoline-4-amines, 1H-Indazole-6-amine in basic medium. The electro luminescence and photophysical properties of a series of benzo[g][1,8]naphthyridines 5(a–d), 6(a–d) and 2-chloroquinoline-4-amines 3(a–f) are reported and investigated with the aim of arriving at good fluorescent materials. Moreover, the effect of electron donor-acceptor substituent on fluorescence properties of all molecules has been investigated along with their fluorescent quantum yields. Furthermore we analyzed for band gap energy associated with HOMO-LUMO, through density functional (DFT M06-HF) studies. The experimental observations are in close agreement with the theoretical calculation. All the synthesized compounds were identified on the basis of their NMR, Mass spectral data analyses.

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.

Synthesis of aryl-heteroaryl ureas (AHUs) based on 4-aminoquinoline and their evaluation against the insulin-like growth factor receptor (IGF-1R)

The insulin-like growth factor receptor (IGF-1R) is a receptor tyrosine kinase (RTK) involved in all stages of the development and propagation of breast and other cancers. The inhibition of IGF-1R by small molecules remains a promising strategy to treat cancer. Herein, we explore SAR around previously characterized lead compound (1), which is an aryl-heteroaryl urea (AHU) consisting of 4-aminoquinaldine and a substituted aromatic ring system. A library of novel AHU compounds was prepared based on derivatives of the 4-aminoquinoline heterocycle (including various 2-substituted derivatives, and naphthyridines). The compounds were screened for in vitro inhibitory activity against IGF-1R, and several compounds with improved activity (3-5 μM) were identified. Furthermore, a computational docking study was performed, which identifies a fairly consistent lowest energy mode of binding for the more-active set of inhibitors in this series, while the less-active inhibitors do not adopt a consistent mode of binding.

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.