Table of Contents
Is hydroxyquinoline a quinolone?
4-Quinolone is an organic compound derived from quinoline. It and 2-quinolone are the two most important parent (meaning simplified) quinolones. 4-Quinolone exists in equilibrium with a minor tautomer, 4-hydroxyquinoline (CAS#611-36-9).
What is the mechanism of action of quinolones?
The mechanism of quinolone inhibition occurs via formation of a ternary cleavage complex with the topoisomerase enzyme and DNA Figure 2 (Hiasa and Shea, 2000).
What are quinolones drugs?
Quinolones are a type of antibiotic. Antibiotics kill or inhibit the growth of bacteria. There are five different quinolone classes. In addition, another class of antibiotic, called fluoroquinolones, were derived from quinolones by modifying their structure with fluorine.
How do you synthesize quinoline?
Quinolines may be obtained by the Skraup synthesis. This involves heating aniline or a substituted aniline with glycerol in the presence of sulphuric acid, ferrous sulphate and nitrobenzene. The reaction is complex. It involves dehydration of glycerol by means of sulphuric acid to give acrolein.
Which reaction is used for the synthesis of quinoline?
Skraup synthesis
The Skraup synthesis is a chemical reaction used to synthesize quinolines. It is named after the Czech chemist Zdenko Hans Skraup (1850-1910). In the archetypal Skraup reaction, aniline is heated with sulfuric acid, glycerol, and an oxidizing agent such as nitrobenzene to yield quinoline.
What does quinoline mean?
Definition of quinoline 1 : a pungent oily nitrogenous base C9H7N obtained usually by distillation of coal tar or by synthesis from aniline that is the parent compound of many alkaloids, drugs, and dyes.
What pharmaceutical makes hydroxyquinoline?
Synthexim develops and produces specialty chemical products. The Company offers advanced intermediates, active ingredients for the pharmaceutical industry, 8-hydroxyquinoline derivatives, and controlled substances.
Is chloroquine a quinolone?
Chloroquine and hydroxychloroquine belong to the quinolone family. Although their therapeutic and toxic doses differ, they are related drugs with similar clinical indications for use and similar manifestations of retinal toxicity. Initially, chloroquine was given for malaria prophylaxis and treatment.
What is the structure of hydroxyquinoline?
Hydroxyquinoline Structure. That sounds complicated, so let’s break it down into simpler terms. A heterocycle is a compound that contains a ring, and the prefix -hetero means that there is an atom within the ring that’s NOT carbon. In the case of a quinoline, the atom that’s not carbon is nitrogen.
How to synthesize 4-hydroxy-2(1 h )-quinolones?
The easiest method for the synthesis 4-hydroxy-2 (1 H )-quinolones 1 was previously considered to be the reaction of anilines using malonic acid equivalents ( Method A ). Some other more specialized methods are the reaction of anthranilic acid derivatives ( Method B) or alternatively by methods C or D (Scheme 1 ).
How do you make hydroxyquinoline?
Eight-hydroxyquinoline can be made by simply reacting glycerol with 2-aminophenol in the presence of sulfuric acid. This reaction is called a Skraup synthesis, named after the Czech chemist Zdenko Hans Skraup. The nice thing about this reaction is that it constructs a hydroxyquinoline using cheap and commercially available starting materials.
Can 4-hydroxy-2-quinolones be synthesized as heteroannelated derivatives?
The interesting pharmaceutical and biological activities of 4-hydroxy-2-quinolones make them valuable in drug research and development. Hence, many publications have recently dealt with their synthetic analogous and the synthesis of their heteroannelated derivatives.