1084-32-8

Usage

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

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

Downstream Products

• 33497-91-5 8-chloro-5,7-dinitroquinoline 
• 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 

Relevant academic research and scientific papers

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

Investigating biological activity spectrum for novel quinoline analogues

The lack of the wide spectrum of biological data is an important obstacle preventing the efficient molecular design. Quinoline derivatives are known to exhibit a variety of biological effects. In the current publication, we tested a series of novel quinol

Protonation of Anionic σ-Complexes of 5,7-Dinitroquinolin-8-ol

Abstract: The reaction of 5,7-dinitroquinolin-8-ol with NaBH4 produces a reactive hydride σ-complex, the treatment of which with a solution of acetic acid gives 5,7-dinitro-5,6-dihydroquinolin-8-ol. The protonation of the acetone σ-complex of 5,7-dinitroquinolin-8-ol forms a mixture of the tautomers 5,7-dinitro-6-(2-oxopropyl)-6,7-dihydroquinoline-8(5H)-one and 5,7-dinitro-5,6-dihydro-6-(2-oxopropyl)quinolin-8-ol, with a predominance of the latter.

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%.

From Surprising Solvothermal Reaction to Uncommon Zinc(II)-Catalyzed Aromatic C-H Activation Reaction for Direct Nitroquinoline Synthesis

In this work, we first found a surprising solvothermal reaction for direct dinitration of quinoline derivative. To explore the application in direct nitroquinoline synthesis, this reaction was subsequently modified as an equivalent reaction in a Schlenk tube. More significantly, after a constant attempt, nitrated derivative was obtained in optimized condition with a zinc(II) sulfate catalyst, where some substrates with strong electron-withdrawing group were first nitrated by a directly catalyzed condition. This new zinc(II)-catalyzed aromatic C-H activation reaction is the first example of direct dinitration by a single catalyst, which will be a new facile and environmentally friendly strategy to access synthetically useful nitroquinoline derivative.

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.

Synthesis and spectral-kinetic investigation of fulgimide-based photochromic autocomplexes of the dinitroquinoline series

Two new hybrid compounds, which belong to autocomplexes of the dinitroquinoline series and contain an NH spacer and fragments of photochromic fulgimides as donor components, were synthesized. These autocomplexes were used as ligands in the synthesis of cobalt-containing metal chelates. The spectral-kinetic study revealed that these compounds exhibit photochromism. The introduction of photochromic fulgimide moieties into the autocomplexes has no substantial effect on the spectral properties of the latter but influences the kinetics of photochromic transformations by decreasing their efficiency. Chelate complexes of the hybrid compounds with cobalt ions are characterized by the lowest efficiency of photochromic transformations due to a decrease in the intensity of activating radiation as a result of its absorption by the dinitroquinoline moieties, which are not conjugated with fragments of photochromic compounds.

Preparation and evaluation of sulfur-containing metal chelators

With a view to probe the structure and function of G-protein coupled receptors the synthesis of functionalized 8-mercaptoquinoline derivatives and 2-(2-pyridyl)thiophenol was achieved. A fluorescence-based method for determining the affinity of these metal chelators toward zinc ions was developed.

Thermal Fragmentations of Nitrated 8-Quinolinols

8-Quinolinols which are substituted in the aromatic nucleus by nitro-, chloro-, or by sulfonic acid groups underwent a neat thermal fragmentation upon heating in 75percent nitric acid as reaction medium yielding 2,3-dicarboxypyridinium nitrate.The scope and the mechanism of these reactions are discussed.

Inverse Electron Demand Diels-Alder Reactions of Heterocyclic Aza Dienes. Studies on the Total Synthesis of Lavendamycin: Investigative Studies on the Preparation of the CDE β-Carboline Ring System and AB Quinoline-5,8-quinone Ring System

The investigation and utilization of the inverse electron demand cycloaddition of 3,5,6-tris(ethoxycarbonyl)-1,2,4-triazine with electron-rich olefins and the subsequent implementation of a palladium(0)-mediated β-carboline synthesis for the preparation of the CDE ring system of lavendamycin are detailed.Studies on the introduction and preparation of the 7-aminoquinoline-5,8-quinone AB ring system of lavendamycin are described.