16498-85-4

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-chloro-3-quinolinecarboxylate is used as a key intermediate in the synthesis of fused piperidinyl bicyclic compounds. These compounds act as modulators of the C5a receptor, which plays a crucial role in the immune system. By modulating the C5a receptor, these compounds can potentially be used to treat various inflammatory and autoimmune diseases, as well as conditions related to the complement system.
In the synthesis of fused piperidinyl bicyclic compounds, Methyl 2-chloro-3-quinolinecarboxylate serves as a building block that can be further functionalized and modified to create a diverse range of molecules with specific biological activities. Its reactivity and structural features make it an attractive candidate for the development of new drugs and therapeutic agents.
Overall, Methyl 2-chloro-3-quinolinecarboxylate is a valuable chemical entity with significant potential in the pharmaceutical industry, particularly in the development of novel modulators of the C5a receptor and other related targets. Its unique structure and properties contribute to the ongoing efforts to discover and design new drugs for the treatment of various diseases and conditions.

Upstream product

• 67-56-1 methanol 
• 73776-25-7 2-chloro-3-quinolinecarboxylic acid 
• 62-53-3 aniline 
• 103-84-4 Acetanilid 
• 91301-03-0 3-formyl-2-quinolone 
• 73568-25-9 2-chloro-3-quinoline carboxaldehyde 

Downstream Products

• 115307-42-1 methyl 2-(4-methoxyphenyl)-3-quinolinecarboxylate 

Relevant academic research and scientific papers

COMBINATION PHARMACEUTICAL AGENTS AS RSV INHIBITORS

The present invention relates to pharmaceutical agents administered to a subject either in combination or in series for the treatment of a Respiratory Syncytial Virus (RSV) infection, wherein treatment comprises administering a compound effective to inhibit the function of the RSV and an additional compound or combinations of compounds having anti-RSV activity.

BENZODIAZEPINE DERIVATIVES AS RSV INHIBITORS

The present invention discloses compounds of Formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof: which inhibit Respiratory Syncytial Virus (RSV). The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from RSV infection. The invention also relates to methods of treating an RSV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

Synthesis and Herbicidal Activity of Triketone-Quinoline Hybrids as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) is one of the most important targets for herbicide discovery. In the search for new HPPD inhibitors with novel scaffolds, triketone-quinoline hybrids were designed and subsequently optimized on the basis of the structure-activity relationship (SAR) studies. Most of the synthesized compounds displayed potent inhibition of Arabidopsis thaliana HPPD (AtHPPD), and some of them exhibited broad-spectrum and promising herbicidal activity at the rate of 150 g ai/ha by postemergence application. Most promisingly, compound III-l, 3-hydroxy-2-(2-methoxy-7-(methylthio)quinoline-3-carbonyl)cyclohex-2-enone (Ki = 0.009 ～M, AtHPPD), had broader spectrum of weed control than mesotrione. Furthermore, compound III-l was much safer to maize at the rate of 150 g ai/ha than mesotrione, demonstrating its great potential as herbicide for weed control in maize fields. Therefore, triketone-quinoline hybrids may serve as new lead structures for novel herbicide discovery.

Iodine-mediated solvent-controlled selective electrophilic cyclization and oxidative esterification of o-alkynyl aldehydes: An easy access to pyranoquinolines, pyranoquinolinones, and isocumarins

Chemoselective behavior of iodine in different solvents in the electrophilic iodocyclization of o-alkynyl aldehydes is described. o-Alkynyl aldehydes 3a-t on reaction with I2 in CH2Cl2 with appropriate nucleophiles provides pyrano[4,3-b]quinolines 4a-f, via formation of cyclic iodonium intermediate Q; however, using alcohols as a solvent as well as nucleophile, o-alkynyl esters 5a-y were obtained selectively in good to excellent yields via formation of hypoiodide intermediate R. Subsequently, o-alkynyl esters were converted in to pyranoquinolinones 6a-i and isocoumarin 6j by electrophilic iodocyclization. This developed oxidative esterification provides a novel access for the chemoselective synthesis of esters 5q-u from aldehydes 3n-p without oxidizing primary alcohol present in the substrate.

Vilsmeier-Haack reagent: A facile synthesis of 2-chloro-3-formylquinolines from N-arylacetamides and transformation into different functionalities

A simple and regioselective synthesis of 2-chloro-3-formylquinolines through Vilsmeier-Haack cyclisation of N-arylacetamides has been reported. The cyclisation is facilitated by N-arylacetamides bearing electron donating groups at m-position. However, yields of quinolines having electron donating groups are good in all cases. Further, the nucleophilic substitution reaction of the quinolines is also investigated. Similarly, the formyl group in the quinolines is subjected to further transformation into cyano (CAN-NH3) and alkoxycarbonyl (NIS-K2CO3/alcohols) groups to afford corresponding 3-cyano and 3-alkoxycarbonylquinolines, respectively.