53985-73-2

Basic information

• Product Name: 4-Hydroxy-7-trifluoromethoxyquinoline-3-carboxylic acid ethyl ester
• Synonyms: 4-Hydroxy-7-trifluoromethoxyquinoline-3-carboxylic acid ethyl ester
• CAS NO: 53985-73-2
• Molecular Formula: C₁₃H₁₀F₃NO₄
• Molecular Weight: 301.2180096
• Mol File: 53985-73-2.mol

Chemical Properties

• Boiling Point: 338°C at 760 mmHg
• Flash Point: 158.2°C
• Appearance: /
• Density: 1.434g/cm³
• Vapor Pressure: 5.15E-05mmHg at 25°C
• Refractive Index: 1.557
• CAS DataBase Reference: 4-Hydroxy-7-trifluoromethoxyquinoline-3-carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-7-trifluoromethoxyquinoline-3-carboxylic acid ethyl ester(53985-73-2)
• EPA Substance Registry System: 4-Hydroxy-7-trifluoromethoxyquinoline-3-carboxylic acid ethyl ester(53985-73-2)

Safety Data

• Hazardous Substances Data: 53985-73-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H10F3NO4/c1-2-20-12(19)9-6-17-10-5-7(21-13(14,15)16)3-4-8(10)11(9)18/h3-6H,2H2,1H3,(H,17,18)

Upstream product

• 1535-73-5 m-trifluoromethoxyaniline 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 

Downstream Products

• 890841-23-3 ethyl 4-chloro-7-(trifluoromethoxy)quinoline-3-carboxylate 
• 1373767-09-9 ethyl 2-(3-methoxyphenyl)-4-oxo-7-(trifluoromethoxy)-1,4-dihydroquinoline-3-carboxylate 
• 1373767-10-2 ethyl 4-oxo-7-(trifluoromethoxy)-2-(3-(trifluoromethoxy)phenyl)-1,4-dihydroquinoline-3-carboxylate 

Relevant articles and documents

Structural development of a type-1 ryanodine receptor (RyR1) Ca2+-release channel inhibitor guided by endoplasmic reticulum Ca2+ assay

Type-1 ryanodine receptor (RyR1) is a calcium-release channel localized on sarcoplasmic reticulum (SR) of the skeletal muscle, and mediates muscle contraction by releasing Ca2+ from the SR. Genetic mutations of RyR1 are associated with skeletal muscle diseases such as malignant hyperthermia and central core diseases, in which over-activation of RyR1 causes leakage of Ca2+ from the SR. We recently developed an efficient high-throughput screening system based on the measurement of Ca2+ in endoplasmic reticulum, and used it to identify oxolinic acid (1) as a novel RyR1 channel inhibitor. Here, we designed and synthesized a series of quinolone derivatives based on 1 as a lead compound. Derivatives bearing a long alkyl chain at the nitrogen atom of the quinolone ring and having a suitable substituent at the 7-position of quinolone exhibited potent RyR1 channel-inhibitory activity. Among the synthesized compounds, 14h showed more potent activity than dantrolene, a known RyR1 inhibitor, and exhibited high RyR1 selectivity over RyR2 and RyR3. These compounds may be promising leads for clinically applicable RyR1 channel inhibitors.

Synthesis and biological evaluation of new nucleosides derived from trifluoromethoxy-4-quinolones

The synthesis of new nucleoside derivatives from 6- and 7-trifluoromethoxy-4-quinolones is described. The present synthesis is a combination of the Gould-Jacobs reaction for the preparation of 4-quinolones and a modified Vorbrüggen reaction for the construction of nucleoside derivatives. The target compounds were tested against murine gammaherpesvirus MHV-68 type.

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.