77156-85-5

Basic information

• Product Name: Ethyl 4-chloro-7-methoxyquinoline- 3-carboxylate
• Synonyms: Ethyl 4-chloro-7-methoxyquinoline- 3-carboxylate;Ethyl 4-chloro-7-methoxy-3-quinolinecarboxylate;Ethyl 4-chloro-7-Methoxyquinoline-3-caroboxylate;4-Chloro-7-methoxy-quinoline-3-carboxylic acid ethyl ester;4-Chloro-7-methoxy-quinoline-3-carboxylic acid methyl ester
• CAS NO: 77156-85-5
• Molecular Formula: C₁₃H₁₂ClNO₃
• Molecular Weight: 265.7
• Mol File: 77156-85-5.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 366.9 °C at 760 mmHg
• Flash Point: 175.7 °C
• Appearance: /
• Density: 1.282 g/cm³
• Vapor Pressure: 1.42E-05mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: Ethyl 4-chloro-7-methoxyquinoline- 3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 4-chloro-7-methoxyquinoline- 3-carboxylate(77156-85-5)
• EPA Substance Registry System: Ethyl 4-chloro-7-methoxyquinoline- 3-carboxylate(77156-85-5)

Safety Data

• Hazardous Substances Data: 77156-85-5(Hazardous Substances Data)

Usage

General Description

Ethyl 4-chloro-7-methoxyquinoline- 3-carboxylate is a chemical compound with the molecular formula C13H11ClNO3. It is a derivative of quinoline, a heterocyclic aromatic compound. This chemical is commonly used in the synthesis of pharmaceuticals and agrochemicals. The presence of the chloro and methoxy groups in the compound make it a useful building block for the development of new drugs and pesticides. It has been studied for its potential biological activities and has shown promise as an antitumor and antibacterial agent. Additionally, its ester functionality makes it a useful intermediate for the preparation of various organic compounds.

InChI:InChI=1/C13H12ClNO3/c1-3-18-13(16)10-7-15-11-6-8(17-2)4-5-9(11)12(10)14/h4-7H,3H2,1-2H3

Upstream product

• 536-90-3 m-Anisidine 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 71083-05-1 7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 
• 63463-15-0 ethyl 4-hydroxy-7-methoxyquinoline-3-carboxylate 
• 56881-19-7 Diethyl 2-<(3-methoxyphenylamino)methylene>malonate 

Downstream Products

• 852062-08-9 4-chloro-7-methoxyquinoline-3-carboxylic acid 
• 659730-27-5 7-hydroxyquinoline-3-carboxylic acid 
• 1373766-78-9 6-(dimethylamino)hexyl 7-methoxy-4-oxo-2-(3-phenoxyphenyl)-1,4-dihydroquinoline-3-carboxylate 
• 1373766-77-8 3-(dimethylamino)propyl 7-methoxy-4-oxo-2-(3-phenoxyphenyl)-1,4-dihydroquinoline-3-carboxylate 
• 1373766-76-7 2-(dimethylamino)ethyl 7-methoxy-4-oxo-2-(3-phenoxyphenyl)-1,4-dihydroquinoline-3-carboxylate 
• 1373766-75-6 2-morpholinoethyl 7-methoxy-4-oxo-2-(3-phenoxyphenyl)-1,4-dihydroquinoline-3-carboxylate 
• 1373766-74-5 2-morpholinoethyl 7-methoxy-4-oxo-2-(3-phenoxyphenyl)-1,4-dihydroquinoline-3-carboxylate 
• 1373767-04-4 ethyl 2-(3-fluoro-5-methoxyphenyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 1373767-03-3 ethyl 2-(3,5-dimethoxyphenyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 1373767-02-2 ethyl 2-(3-(hydroxymethyl)phenyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate 

Relevant articles and documents

Design and Synthesis of Novel Deuterated Ligands Functionally Selective for the γ-Aminobutyric Acid Type A Receptor (GABAAR) α6 Subtype with Improved Metabolic Stability and Enhanced Bioavailability

Recent reports indicate that α6β2/3γ2 GABAAR selective ligands may be important for the treatment of trigeminal activation-related pain and neuropsychiatric disorders with sensori-motor gating deficits. Based on 3 functionally α6β2/3γ2 GABAAR selective pyrazoloquinolinones, 42 novel analogs were synthesized, and their in vitro metabolic stability and cytotoxicity as well as their in vivo pharmacokinetics, basic behavioral pharmacology, and effects on locomotion were investigated. Incorporation of deuterium into the methoxy substituents of the ligands increased their duration of action via improved metabolic stability and bioavailability, while their selectivity for the GABAAR α6 subtype was retained. 8b was identified as the lead compound with a substantially improved pharmacokinetic profile. The ligands allosterically modulated diazepam insensitive α6β2/3γ2 GABAARs and were functionally silent at diazepam sensitive α1β2/3γ2 GABAARs, thus no sedation was detected. In addition, these analogs were not cytotoxic, which render them interesting candidates for treatment of CNS disorders mediated by GABAAR α6β2/3γ2 subtypes.

LIGANDS SELECTIVE TO ALPHA 6 SUBUNIT-CONTAINING GABAA RECEPTORS ANS THEIR METHODS OF USE

Provided herein are novel pyrazoloquinolinone compounds and method of using such compounds to treat disorders such as neuropsychiatric disorders with sensorimotor gating deficits, such as schizophrenia, tic disorders, attention deficit hyperactivity disorder, obsessive compulsive disorder, panic disorder, Huntington's disease and nocturnal enuresis;depression; temporomandibular myofascial pain; disorders of trigeminal nerve, such as trigeminal neuralgia and trigeminal neuropathy; migraine; and tinnitus.

Lead optimization of 3-carboxyl-4(1 H)-quinolones to deliver orally bioavailable antimalarials

Malaria is a protozoal parasitic disease that is widespread in tropical and subtropical regions of Africa, Asia, and the Americas and causes more than 800,000 deaths per year. The continuing emergence of multidrug-resistant Plasmodium falciparum drives the ongoing need for the development of new and effective antimalarial drugs. Our previous work has explored the preliminary structural optimization of 4(1H)-quinolone ester derivatives, a new series of antimalarials related to the endochins. Herein, we report the lead optimization of 4(1H)-quinolones with a focus on improving both antimalarial potency and bioavailability. These studies led to the development of orally efficacious antimalarials including quinolone analogue 20g, a promising candidate for further optimization.