3747-74-8

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(Chloromethyl)quinoline hydrochloride is used as a key building block for the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications, including antimalarial, anticancer, and antibacterial agents. The presence of the chloromethyl group facilitates the attachment of different functional groups, enabling the creation of diverse drug candidates with improved pharmacological properties.
Used in Biologically Active Compounds:
In addition to its pharmaceutical applications, 2-(Chloromethyl)quinoline hydrochloride is also used in the synthesis of biologically active compounds. These compounds can be employed as research tools, probes, or lead compounds for the development of new therapeutic agents. The versatility of the quinoline core, combined with the reactivity of the chloromethyl group, makes it an attractive starting point for the design and synthesis of novel bioactive molecules.
Used in Fluorescent Zinc Sensors:
2-(Chloromethyl)quinoline hydrochloride is used as a precursor for the preparation of quinoline-based fluorescent zinc sensors. These sensors are employed as fluorescent probes for the detection and quantification of zinc ions in various biological and environmental samples. The incorporation of the quinoline moiety into the sensor design enhances the selectivity and sensitivity of the probe, making it a valuable tool for zinc ion analysis.

InChI:InChI=1/C5H5ClN2.ClH/c6-4-5-7-2-1-3-8-5;/h1-3H,4H2;1H

Upstream product

• 91-63-4 2-methylquinoline 
• 67-56-1 methanol 
• 530-64-3 quinoline hydrochloride 

Downstream Products

• 121289-78-9 4-(quinolin-2-yl-methoxy)phenylacetic acid 
• 150235-40-8 [4-(quinolin-2-ylmethoxy)phenyl]methanol 
• 107813-60-5 3-(Quinolin-2-ylmethoxy)-benzonitrile 
• 107813-64-9 4-<3-(2-quinolinylmethoxy)phenoxy>butyronitrile 
• 107813-80-9 4-[2-(2-quinolylmethyloxy)phenoxy]butyronitrile 
• 103119-12-6 2-(3-Hexanoylphenoxy)methyl quinoline 
• 114497-65-3 4-<4-(2-quinolinylmethoxy)phenoxy>butyronitrile 
• 101910-24-1 2-[3-(1-hydroxyhexyl)phenoxymethyl]quinoline 
• 304024-21-3 4-[3-Methyl-5-(quinolin-2-ylmethoxy)-phenoxy]-butyronitrile 
• 103119-21-7 2-[[3-(formyl)phenoxy]methyl]quinoline 
• 136727-11-2 2-<(methylamino)methyl>quinoline 
• 123432-18-8 1-phenyl-2-(2-quinolylmethyl)isothiourea dihydrochloride 
• 120159-59-3 4-[(2-quinolinyl)-methoxy]-benzaldehyde 
• 189239-02-9 3-[3-tert-Butylsulfanyl-1-(4-chloro-benzyl)-5-(quinolin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid ethyl ester 

Relevant academic research and scientific papers

Novel heteroaryl selenocyanates and diselenides as potent antileishmanial agents

A series of new selenocyanates and diselenides bearing interesting bioactive scaffolds (quinoline, quinoxaline, acridine, chromene, furane, isosazole, etc.) was synthesized, and their in vitro leishmanicidal activities against Leishmania infantum amastigotes along with their cytotoxicities in human THP-1 cells were determined. Interestingly, most tested compounds were active in the low micromolar range and led us to identify four lead compounds (1h, 2d, 2e, and 2f) with 50% effective dose (ED50) values ranging from 0.45 to 1.27 μM and selectivity indexes of >25 for all of them, much higher than those observed for the reference drugs. These active derivatives were evaluated against infected macrophages, and in order to gain preliminary knowledge about their possible mechanism of action, the inhibition of trypanothione reductase (TryR) was measured. Among these novel structures, compounds 1h (3,5-dimethyl-4-isoxazolyl selenocyanate) and 2d [3,3′-(diselenodiyldimethanediyl)bis(2-bromothiophene)] exhibited good association between TryR inhibitory activity and antileishmanial potency, pointing to 1h, for its excellent theoretical ADME (absorption, distribution, metabolism, and excretion) properties, as the most promising lead molecule for leishmancidal drug design.

The process development of RG 12525 (2-{[4-(Tetrazol-5-ylmethylphenyl)-methoxy]phenoxymethyl}quinoline)

This contribution describes process improvements to provide a practical and cost-effective synthesis for the manufacture of RG 12525 which resulted in a 3-fold increase in overall yield. Improved solvent systems for chlorination and azidation reactions are described. Adjustments to the tetrazole-forming step eliminated azide sublimation and minimised this risk on scale-up. A robust solvent system was found to control the polymorphic form during crystallisation, which had hitherto been difficult due to the near-equivalence of melting points (154 and 157 °C) of the two known forms.