1084-32-8

Basic information

• Product Name: 5,7-DINITROQUINOLIN-8-OL
• Synonyms: 5,7-DINITROQUINOLIN-8-OL
• CAS NO: 1084-32-8
• Molecular Formula: C₉H₅N₃O₅
• Molecular Weight: 235.1531
• Mol File: 1084-32-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 424.7°Cat760mmHg
• Flash Point: 210.6°C
• Appearance: /
• Density: 1.693g/cm³
• Vapor Pressure: 8.21E-08mmHg at 25°C
• Refractive Index: 1.76
• CAS DataBase Reference: 5,7-DINITROQUINOLIN-8-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-DINITROQUINOLIN-8-OL(1084-32-8)
• EPA Substance Registry System: 5,7-DINITROQUINOLIN-8-OL(1084-32-8)

Safety Data

• Hazardous Substances Data: 1084-32-8(Hazardous Substances Data)

Usage

Description

5,7-DINITROQUINOLIN-8-OL, also known as 5,7-Dinitro-8-quinolinol, is a synthetic intermediate with significant antimycobacterial properties. It is a compound derived from the quinoline family, characterized by the presence of nitro groups at the 5 and 7 positions and a hydroxyl group at the 8 position. 5,7-DINITROQUINOLIN-8-OL has demonstrated higher antimycobacterial activity compared to some conventional antibiotics, making it a promising candidate for further research and development in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
5,7-DINITROQUINOLIN-8-OL is used as a synthetic intermediate for the development of new antimycobacterial drugs due to its higher activity against Mycobacterium abscessus and Mycobacterium smegmatis compared to ciprofloxacin (C482500). Its potent antimycobacterial properties make it a valuable compound for creating more effective treatments against drug-resistant tuberculosis and other mycobacterial infections.
Used in Research and Development:
5,7-DINITROQUINOLIN-8-OL is employed in the investigation of structure-activity relationships of nitroxoline derivatives. This research aims to provide new insights into the development of novel cathepsin B inhibitors, which could have potential applications in various therapeutic areas, including cancer treatment and other diseases where cathepsin B plays a role in their progression.

InChI:InChI=1/C9H5N3O5/c13-9-7(12(16)17)4-6(11(14)15)5-2-1-3-10-8(5)9/h1-4,13H

Upstream product

• 15851-63-5 8-hydroxy-7-nitro-quinoline-5-sulfonic acid 
• 31568-82-8 5-nitro-8-quinolinol-7-sulfonic acid 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 84-88-8 8-quinolinol-5-sulfonic acid 
• 3062-35-9 8-hydroxy-quinoline-7-sulphonic acid 
• 148-24-3 8-quinolinol 
• 95-55-6 2-amino-phenol 

Downstream Products

• 13207-71-1 5,7-diamino-quinolin-8-ol; dihydrochloride 
• 145909-55-3 5,7-dinitro-8-(2-hydroxyphenoxy)quinoline 
• 89-00-9 Pyridine-2,3-dicarboxylic acid 
• 16830-25-4 2-carboxy-3-pyridineglyoxylic acid 
• 33497-91-5 8-chloro-5,7-dinitroquinoline 

Relevant articles and documents

Antifungal properties of new series of quinoline derivatives

The series of quinoline derivatives were prepared. The synthetic approach, analytical, and spectroscopic data of all synthesized compounds are presented. All the prepared derivatives were analyzed using the reversed-phase high performance liquid chromatog

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Method for preparing 4, 5-dinitroimidazole by adopting microchannel reactor

The invention discloses a method for preparing 4, 5-dinitroimidazole by adopting a microchannel reactor. According to the method, raw material mixing is enhanced by using a micromixer, and the mixinguniformity is limited by uneven flow fields generated by stirring in a prior reactor; a flow focusing technology adopted by the HPIMM micromixer can force two fluid thin layers to flow through a convergence chamber so as to generate efficient and uniform thin layer contact reaction, and the stoichiometric ratio of reactants is precisely controlled, so that the consumption of strong acid is reducedfrom the source, and the generation of multi-nitration byproducts caused by acid amount and temperature change during the reaction in a prior kettle reactor is eliminated, mass transfer resistance iseliminated, generation of hot spots is avoided, and the problem that the 4, 5-dinitroimidazole has great safety problems caused by intense heat release in the prior reactor is solved. According to the invention, a microsystem is utilized to carry out the synthesis of 4-nitroimidazole and 4, 5-dinitroimidazole, the yields can reach to 96.1% and 92.4%.

Development of new cathepsin b inhibitors: Combining bioisosteric replacements and structure-based design to explore the structure-activity relationships of nitroxoline derivatives

Human cathepsin B has many house-keeping functions, such as protein turnover in lysosomes. However, dysregulation of its activity is associated with numerous diseases, including cancers. We present here the structure-based design and synthesis of new cathepsin B inhibitors using the cocrystal structure of 5-nitro-8-hydroxyquinoline in the cathepsin B active site. A focused library of over 50 compounds was prepared by modifying positions 5, 7, and 8 of the parent compound nitroxoline. The kinetic parameters and modes of inhibition were characterized, and the selectivities of the most promising inhibitors were determined. The best performing inhibitor 17 was effective in cell-based in vitro models of tumor invasion, where it significantly abrogated invasion of MCF-10A neoT cells. These data show that we have successfully explored the structure-activity relationships of nitroxoline derivatives to provide new inhibitors that could eventually lead to compounds with clinical usefulness against the deleterious effects of cathepsin B in cancer progression.