42606-37-1

Basic information

• Product Name: 5-Nitro-6-aminoquinoline
• Synonyms: 5-Nitro-6-aminoquinoline;5-Nitroquinolin-6-amine
• CAS NO: 42606-37-1
• Molecular Formula: C9H7N3O2
• Molecular Weight: 189.1708
• Mol File: 42606-37-1.mol

Chemical Properties

• Boiling Point: 403.5°Cat760mmHg
• Flash Point: 197.8°C
• Appearance: /
• Density: 1.445g/cm³
• Vapor Pressure: 1.02E-06mmHg at 25°C
• Refractive Index: 1.743
• PKA: 3.46±0.15(Predicted)
• CAS DataBase Reference: 5-Nitro-6-aminoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Nitro-6-aminoquinoline(42606-37-1)
• EPA Substance Registry System: 5-Nitro-6-aminoquinoline(42606-37-1)

Safety Data

• Hazardous Substances Data: 42606-37-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 30, p. 711, 1952 DOI: 10.1139/v52-084

InChI:InChI=1/C9H7N3O2/c10-7-3-4-8-6(2-1-5-11-8)9(7)12(13)14/h1-5H,10H2

Upstream product

• 86984-32-9 6‐chloro‐5‐nitroquinoline 
• 98203-04-4 6-bromo-5-nitroquinoline 
• 607-34-1 5-nitroquinoline 
• 74-89-5 methylamine 

Downstream Products

• 42143-23-7 5,6-diaminoquinoline 
• 76180-97-7 2-amino-3H-imidazo<4,5-f>quinoline 
• 76180-96-6 2-Amino-3-methylimidazo[4,5-f]quinoline 
• 87967-75-7 2,3-diphenyl-pyrido[3,2-f]quinoxaline 
• 93201-85-5 2-methyl-1(3)H-imidazo[4,5-f]quinoline 

Relevant articles and documents

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.

HETEROARYL COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are heteroaryl compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. In one embodiment, the compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as CNS disorders and metabolic disorders, including, but not limited to, e.g., neurological disorders, psychosis, schizophrenia, obesity, and diabetes.

Vicarious nucleophilic amination of nitroquinolines by 1,1,1- trimethylhydrazinium iodide

(Chemical Equation Presented) The amination of 3-, 5-, 6-, 7- and 8-nitroquinoline via the vicarious nucleophilic substitution of hydrogen (VNS) with 1,1,1-trimethylhydrazinium iodide (TMHI) in the presence of t-BuOK in DMSO was studied. The amination occurs regioselectively giving ortho or ortho and para isomers relative to the nitro group with a high yield (95-86%). 2-Nitroquinoline does not undergo vicarious amination but displacement of the labile nitro group by an amino group occurs and then transformation to an imine compound and hydrolysis gives 2(1H)-quinolinone.

Vicarious nucleophilic amination of Nitroquinolines with 4-amino-1,2,4-triazole

3-, 5-. 6-, 7- and 8-Nitroquinolines react with 4-amino-l,2,4-triazole in basic medium (potassium tert-butoxide-dimethyl sulfoxide) giving amino products of the vicarious nucleophilic substitution (VNS) of hydrogen, predominantly at ortho position to the nitro group, except 8-nitroquinoline, which reacts at para position. Additionally, furazano[3,4-f]- and furazano[3,4-zh]quinoline were obtained in the case of 5- and 8- nitroquinoline, respectively. 2-Nitroquinoline was aminated to 2-quinolino(l,2,4-triazol-4-yl)amine in these conditions.

Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen: Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides

A new reaction of sulfenamides with electrophilic arenes under basic conditions is described. The σ adducts formed from nitroarenes and the anions of sulfenamides undergo elimination of thiol to produce the corresponding o- and/or p-nitroanilines. This reaction is analogous to the known alkylation and hydroxylation of nitroarenes via the vicarious nucleophilic substitution of hydrogen (VNS). The reaction gives access to a wide range of substituted nitroanilines, nitronaphthylamines, and aminoheterocycles. By means of the reaction with N-alkyl- and N-arylsulfenamides, it is possible to obtain N-alkylnitroanilines and nitrodiarylamines. By varying the structure of sulfenamide and the reaction conditions, particularly the nature and concentration of the base, it is possible to control the orientation of animation.

Oxidative Methylamination of Nitroquinolines

3-, 5-, 6-, 7- and 8-nitroquinoline as well as 5,7- and 6,8-dinitroquinoline are methylaminated with a liquid methylamine solution of potassium permanganate (LMA/PP) to the corresponding mono- and bis(methylamino)-substituted compounds. 2-Nitroquinoline is aminated with LMA/PP to 2-(methylamino)quinoline.The intermediate methylamino ?-adducts of 3-nitro- and 5,7- and 6,8-dinitroquinoline are detected by 1H-NMR spectroscopy.Quantum chemical calculations for the mononitroquinolines suggest that the experimentally observed regioselectivity of the methylamination is controlled by an interaction of frontal molecular orbitals (FMO) of the reagents. Key Words: Methylaminations / ?-Adducts, methylamino / Calculations, FMO / Quinolines / Aminations

Frontier Orbital Interactions in the Regioselectivity of the Amination of Nitroquinolines by Liquid Ammonia/Potassium Permanganate

5-Nitro-,6-nitro-,7-nitro-,8-nitro-,and 2-nitroquinoline and 5,7-dinitro and 6,8-dinitroquinoline were aminated in a liquid ammonia solution of potassium permanganate. 8-Nitro and 2-nitroquinoline were found to be unreactive.The intermediary ?-adducts,formed between 5,7-dinitro- and 6,8-dinitroquinoline and liquid ammonia, could be detected by 1H NMR spectroscopy.FMO calculations nicely confirm the experimentally observed regioselectivity of the amination.