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Usage

Uses

Used in Organic Synthesis:
3-Hydroxyquinoline N-oxide is used as a reagent in the synthesis of organic compounds, facilitating the creation of a variety of chemical products due to its unique structure and reactivity.
Used in Pharmaceutical Production:
As an intermediate, 3-Hydroxyquinoline N-oxide plays a crucial role in the production of pharmaceuticals, contributing to the development of new drugs and medicines.
Used in Materials Science:
3-Hydroxyquinoline N-oxide is utilized as a building block in the construction of organic electronic devices, taking advantage of its chemical and physical properties to enhance device performance.
Used in Antibacterial Applications:
3-Hydroxyquinoline N-oxide is used as an antibacterial agent, effective in inhibiting the growth of certain bacteria, which can be instrumental in the development of new antimicrobial treatments.
Used in Antitumor Applications:
3-Hydroxyquinoline N-oxide is also studied for its antitumor properties, showing promise in the inhibition of cancer cell growth, potentially leading to advancements in cancer therapy.

Upstream product

• 580-18-7 3-hydroxyquinoline 
• 22615-00-5 3-bromoquinoline N-oxide 

Downstream Products

• 15462-43-8 2-cyano-3-hydroxyquinoline 

Relevant academic research and scientific papers

Setup of 4-Prenylated Quinolines through Suzuki-Miyaura Coupling for the Synthesis of Aurachins A and B

A polyprenyl side chain could be introduced into the heterocyclic quinoline moiety through Suzuki-Miyaura coupling of the corresponding quinoline-N-oxide with a polyprenyl boronic acid. This tool could be utilized for the synthesis of the natural product

Synthesis of 8-Aminoquinolines by Using Carbamate Reagents: Facile Installation and Deprotection of Practical Amidating Groups

Described herein is the development of practical routes to 8-aminoquinolines by using readily installable and easily deprotectable amidating reagents. Two scalable procedures were optimized under RhIII-catalyzed conditions: i) the use of pre-generated chlorocarbamates and ii) a two-step one-pot process that directly employs carbamates. Both approaches are highly convenient for the gram-scale synthesis of 8-aminoquinolines under mild conditions. Facile deprotection of the synthetically versatile amidating groups was achieved under the Pd-catalyzed transfer hydrogenation conditions with simultaneous deoxygenation of quinoline N-oxides, thus yielding 8-aminoquinolines in excellent overall efficiency.

Desazadesmethyldesferrithiocin analogues as orally effective iron chelators

Further structure-activity studies of desferrithiocin analogues are carried out. (S)-Desazadesmethyldesferrithiocin, 2-(2-hydroxyphenyl)-Δ2- thiazoline-4(S)-carboxylic acid, serves as the principal framework in the current paper. Desazadesmethyldesferrithiocin can be structurally altered with facility, and data are already available on its iron-clearing properties and toxicity parameters. Four different kinds of structural modifications of this framework are undertaken: introduction of hydroxy, carboxy, or methoxy groups on the aromatic ring; alteration of the thiazoline ring; increasing the distance between the ligand donor atoms; and benz-fusion of the aromatic rings. The structural modifications described are shown to have a tremendous impact on both the iron clearance and toxicity profiles of the desazadesmethyldesferrithiocin molecule. All of the compounds are assessed in a bile-duct-cannulated rodent model to determine iron clearance efficiency. Ligands which demonstrate an efficiency of greater than 2% are carried forward to the iron-overloaded primate for iron-clearing measurements. Ligands with efficiencies greater than 3% in the primate are then evaluated in a formal toxicity study in rodents. On the basis of the results of the present work, 2-(2,4-dihydroxyphenyl)-Δ2-thiazoline-4(S)-carboxylic acid is a promising candidate for clinical evaluation.

KINETICS OF N-OXIDATION OF COMPOUNDS OF THE QUINOLINE SERIES AND ISOMERIC BENZOQUINOLINES BY PERBENZOIC ACID IN CHLOROFORM AND AQUEOUS DIOXANE

The kinetics of the N-oxidation with perbenzoic acid of 15 derivatives of quinoline and benzoquinoline in chloroform and 19 compounds in 50percent aqueous dioxane at 20, 25, 30, and 35 deg C were subjected to a comparative study.The rate constants, parameters of Arrhenius equation, and the activation energies for the N-oxidation of the indicated monoazines were determined.A scale of the reactivities of derivatives of the quinoline series and benzoquinolines was calculated within the framework of general perturbation theory.