4225-86-9

Basic information

• Product Name: 2-Chloro-8-nitroquinoline
• Synonyms: 2-Chloro-8-nitroquinoline;Quinoline, 2-chloro-8-nitro-;NSC 263744;MFCD00160589
• CAS NO: 4225-86-9
• Molecular Formula: C₉H₅ClN₂O₂
• Molecular Weight: 208.6012
• Mol File: 4225-86-9.mol
• Article Data: 18

Chemical Properties

• Melting Point: 149℃ (ethanol )
• Boiling Point: 351.7 °C at 760 mmHg
• Flash Point: 166.5 °C
• Appearance: /
• Density: 1.484 g/cm³
• Vapor Pressure: 8.18E-05mmHg at 25°C
• Refractive Index: 1.688
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-Chloro-8-nitroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-8-nitroquinoline(4225-86-9)
• EPA Substance Registry System: 2-Chloro-8-nitroquinoline(4225-86-9)

Safety Data

• Hazardous Substances Data: 4225-86-9(Hazardous Substances Data)

Usage

General Description

2-Chloro-8-nitroquinoline is a chemical compound with the molecular formula C9H6ClNO2. It is a yellow solid that is used as an intermediate in the synthesis of pharmaceutical and agricultural chemicals. 2-Chloro-8-nitroquinoline is known for its antimicrobial and antifungal properties and is used in the production of drugs and pesticides. 2-Chloro-8-nitroquinoline is also a potential mutagenic compound and is therefore considered hazardous. It should be handled with proper safety precautions and disposed of according to local regulations to minimize its impact on human health and the environment.

InChI:InChI=1/C9H5ClN2O2/c10-8-5-4-6-2-1-3-7(12(13)14)9(6)11-8/h1-5H

Upstream product

• 612-62-4 2-Chloroquinoline 
• 14753-18-5 8-nitro-quinoline N-oxide 

Downstream Products

• 874498-16-5 (4-chloro-phenyl)-(8-nitro-[2]quinolyl)-amine 
• 7461-11-2 2-chloro-8-aminoquinoline 
• 7461-12-3 8-nitroquinolin-2-ol 
• 7461-12-3 8-Nitroquinolin-2(1H)-one 
• 134829-04-2 8-amino-2-methoxyquinoline 

Relevant articles and documents

Antitrypanosomatid Pharmacomodulation at Position 3 of the 8-Nitroquinolin-2(1H)-one Scaffold Using Palladium-Catalysed Cross-Coupling Reactions

An antikinetoplastid pharmacomodulation study at position 3 of the recently described hit molecule 3-bromo-8-nitroquinolin-2(1H)-one was conducted. Twenty-four derivatives were synthesised using the Suzuki–Miyaura cross-coupling reaction and evaluated in vitro on both Leishmania infantum axenic amastigotes and Trypanosoma brucei brucei trypomastigotes. Introduction of a para-carboxyphenyl group at position 3 of the scaffold led to the selective antitrypanosomal hit molecule 3-(4-carboxyphenyl)-8-nitroquinolin-2(1H)-one (21) with a lower reduction potential (?0.56 V) than the initial hit (?0.45 V). Compound 21 displays micromolar antitrypanosomal activity (IC50=1.5 μm) and low cytotoxicity on the human HepG2 cell line (CC50=120 μm), having a higher selectivity index (SI=80) than the reference drug eflornithine. Contrary to results previously obtained in this series, hit compound 21 is inactive toward L. infantum and is not efficiently bioactivated by T. brucei brucei type I nitroreductase, which suggests the existence of an alternative mechanism of action.

N-(4-acetamidophenyl)-5-acetylfuran-2-carboxamide as a novel orally available diuretic that targets urea transporters with improved PD and PK properties

Urea transporters (UTs) have been identified as new targets for diuretics. Functional deletion of UTs led to urea-selective urinary concentrating defects with relative salt sparing. In our previous study, a UT inhibitor with a diarylamide scaffold, which is denoted as 11a, was demonstrated as the first orally available UT inhibitor. However, the oral bioavailability of 11a was only 4.38%, which obstructed its clinical application. In this work, by replacing the nitro group of 11a with an acetyl group, 25a was obtained. Compared with 11a, 25a showed a 10 times stronger inhibitory effect on UT-B (0.14 μM vs. 1.41 μM in rats, and 0.48 μM vs. 5.82 μM in mice) and a much higher inhibition rate on UT-A1. Moreover, the metabolic stability both in vitro and in vivo and the drug-like properties (permeability and solubility) of 25a were obviously improved compared with those of 11a. Moreover, the bioavailability of 25a was 15.18%, which was 3 times higher than that of 11a, thereby resulting in significant enhancement of the diuretic activities in rats and mice. 25a showed excellent potential for development as a promising clinical diuretic candidate for targeting UTs to treat diseases that require long-term usage of diuretics, such as hyponatremia.

PHENANTHROLINE COMPOUND AND ORGANIC LIGHT EMITTING ELEMENT COMPRISING THE SAME

The present invention relates to an organic electroluminescent device having excellent efficiency characteristics by including a phenanthroline compound and at least one organic layer.