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Quinoline is a heterocyclic aromatic organic compound with the chemical formula C 9 H 7 N. It is a colorless hygroscopic liquid with a strong odor. Aged samples ...
The quinones are a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds", resulting in "a fully conjugated cyclic dione structure".
It is a structural isomer of quinoline. Isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring fused to a pyridine ring. In a broader sense, the term isoquinoline is used to make reference to isoquinoline derivatives.
Zdenko Hans Skraup discovered a way to synthesize substituted quinolines from substituted phenols and described three isomers of oxyquinoline, identifying the structure of 8-hydroxyquinoline. [7] Otto Fischer and his student Karl Bedall made the compound from a sulphonic acid independently at about the same time, but misidentified its structure.
The quinoline alkaloids are mainly found in plants, as in Rutaceae and Rubiaceae, but also in microorganisms and animals. Quinoline is furthermore comprised as a partial structure in the redox factor PQQ (pyrroloquinoline quinone) and in quinoenzymes.
Quinoproteins generally embed the cofactor in a unique, six-bladed [10] beta-barrel structure. Some examples also have a heme C prosthetic group and are termed quinohemoproteins. [11] Although quinoproteins are mostly found in bacteria, a Coprinopsis cinerea (fungus) pyranose dehydrogenase has been shown to use PQQ in its crystal structure. [10]
The basic pharmacophore, or active structure, of the fluoroquinolone class is based upon the quinoline ring system. [60] The addition of the fluorine atom at C6 distinguishes the successive-generation fluoroquinolones from the first-generation of quinolones.
Ring opening in the indole heterocyclic ring could generate new amine and keto functions. The new quinoline heterocycle would then be formed by combining this amine with the aldehyde produced in the tryptamine side-chain cleavage, giving cinchonidinone. For the last step, hydroxylation and methylation gives quinine.