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

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.

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.

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.