73987-37-8

Basic information

• Product Name: 8-CHLORO-4-HYDROXY-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: 8-chloro-4-hydroxy-3-quinolinecarboxylicaciethylester;BUTTPARK 18\09-61;ETHYL 8-CHLORO-4-HYDROXY-3-QUINOLINECARBOXYLATE;ETHYL 8-CHLORO-4-HYDROXYQUINOLINE-3-CARBOXYLATE;8-CHLORO-4-HYDROXY-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER;8-Chloro-4-hydroxy-3-quinolinecarboxylic acid ethyl ester;NSC 102517;Ethyl 4-hydroxy-8-chloroquinoline-3-carboxylate
• CAS NO: 73987-37-8
• Molecular Formula: C₁₂H₁₀ClNO₃
• Molecular Weight: 251.67
• EINECS: -0
• Mol File: 73987-37-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 376.8 °C at 760 mmHg
• Flash Point: 181.7 °C
• Appearance: /
• Density: 1.386
• Vapor Pressure: 7.05E-06mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 8-CHLORO-4-HYDROXY-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 8-CHLORO-4-HYDROXY-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER(73987-37-8)
• EPA Substance Registry System: 8-CHLORO-4-HYDROXY-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER(73987-37-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 73987-37-8(Hazardous Substances Data)

Usage

General Description

The chemical 8-Chloro-4-Hydroxy-Quinoline-3-Carboxylic Acid Ethyl Ester is an ethyl ester derivative of 8-chloro-4-hydroxyquinoline-3-carboxylic acid. It is a synthetic compound with potential antimicrobial and antiparasitic properties, and its structure is similar to chloroquine, a well-known antimalarial drug. This chemical has been studied for its potential use in treating bacterial and parasitic infections, and it is also being investigated for its potential anticancer properties. The ethyl ester form of 8-Chloro-4-Hydroxy-Quinoline-3-Carboxylic Acid may have improved pharmacokinetic properties compared to the parent compound, making it a promising candidate for further research and development in the medical field.

InChI:InChI=1/C12H10ClNO3/c1-2-17-12(16)8-6-14-10-7(11(8)15)4-3-5-9(10)13/h3-6H,2H2,1H3,(H,14,15)

Upstream product

• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 95-51-2 o-chloroaniline 
• 19056-78-1 2-[(2-chlorophenylamino)-methylene]-malonic acid diethyl ester 
• 101-84-8 diphenylether 
• 92-52-4 biphenyl 

Downstream Products

• 874764-65-5 8-chloro-4-hydroxy-quinoline-3-carboxylic acid hydrazide 
• 56824-91-0 4,8-dichloroquinoline-3-carboxylic acid ethyl ester 
• 21617-12-9 4,8-dichloroquinoline 
• 57797-97-4 4-hydroxy-8-chloroquinoline 
• 35975-71-4 8-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 

Relevant articles and documents

3-(Benzo[: D] thiazol-2-yl)-4-aminoquinoline derivatives as novel scaffold topoisomerase i inhibitor via DNA intercalation: Design, synthesis, and antitumor activities

Twenty-seven 3-(benzo[d]thiazol-2-yl)-4-aminoquinoline derivatives have been designed and synthesized as topoisomerase I inhibitors. The in vitro anti-proliferation evaluation against four human cancer cell lines (MGC-803, HepG-2, T24, and NCI-H460) and one normal cell line (HL-7702) indicated that most of them exhibited potent cytotoxicity. Among them, 5a was identified as the most promising candidate with a low IC50 value of about 2.20 ± 0.14 and was selected for further exploration. Spectroscopic analyses and agarose-gel electrophoresis assays indicated that 5a could interact with DNA and strongly inhibit topoisomerase I (Topo I). Further screening of the Topo I activity of compounds 5b, 5c, 5e, 5f, 5h, 5i, 5j, 5l, and 5n suggested that some of the compounds might exert quite a different cytotoxicity profile to that of 5a. Molecular modeling studies confirmed that 5a adopts a unique mode to interact with DNA and Topo I. Other molecular mechanistic studies suggested that the treatment of MGC-803 cells with 5a induces S phase arrest, up-regulates the pro-apoptotic protein, down-regulates the anti-apoptotic protein, activates caspase-3, and subsequently induces mitochondrial dysfunction so as to induce cell apoptosis. The in vivo efficiency of 5a was also evaluated on MGC-803 xenograft nude mice and the relative tumor growth inhibition was 42.4percent at 12 mg kg-1 without an obvious loss in the body weight. This journal is

Quinoline-3-carboxamide containing sulfones as liver X receptor (LXR) agonists with binding selectivity for LXRβ and low blood-brain penetration

A series of quinoline-3-carboxamide containing sulfones was prepared and found to have good binding affinity for LXRβ and moderate binding selectivity over LXRα. The 8-Cl quinoline analog 33 with a high TPSA score, displayed 34-fold binding selectivity for LXRβ over LXRα (LXRβ IC50 = 16 nM), good activity for inducing ABCA1 gene expression in a THP macrophage cell line, desired weak potency in the LXRα Gal4 functional assay, and low blood-brain barrier penetration in rat.

Pharmacomodulations around the 4-oxo-1,4-dihydroquinoline-3-carboxamides, a class of potent CB2-selective cannabinoid receptor ligands: Consequences in receptor affinity and functionality

CB2 receptor selective ligands are becoming increasingly attractive drugs due to the potential role of this receptor in several physiopathological processes. Thus, the development of our previously described series of 4-oxo-1,4-dihydroquinoline-3-carboxamides was pursued with the aim to further characterize the structure-affinity and structure-functionality relationships of these derivatives. The influence of the side chain was investigated by synthesizing compounds bearing various carboxamido and keto substituents. On the other hand, the role of the quinoline central scaffold was studied by synthesizing several 6-, 7-, or 8-chloro-4-oxo-1,4-dihydroquinolines, as well as 4-oxo-1,4-dihydronaphthyridine and 4-oxo-1,4-dihydrocinnoline derivatives. The effect of these modifications on the affinity and functionality at the CB2 receptor was studied and allowed for the characterization of new selective CB2 receptor ligands.