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The reduction of quinoline with sodium borohydride in the presence of acetic acid is known to produce Kairoline A. [15] (C.f. Kairine) Several anti-malarial drugs contain quinoline substituents. These include quinine, chloroquine, amodiaquine, and primaquine. Quinoline is used as a solvent and reagent in organic synthesis. [16]
Quinine is an alkaloid, a naturally occurring chemical compound. [5] How it works as a medicine is not entirely clear. [5] Quinine was first isolated in 1820 from the bark of a cinchona tree, which is native to Peru, [5] [9] [10] and its molecular formula was determined by Adolph Strecker in 1854. [11]
Alkaloids with a quinoline partial structure are widespread and are usually further subdivided according to their occurrence and biogenetic origin. Among the quinoline alkaloids are the cinchona alkaloids quinine and quinidine , which are important due to their therapeutic potential, furthermore cinchonine and cinchonidine, as well as some ...
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".
The aromatic component of the quinine molecule is a quinoline with a methoxy substituent. The amine component has a quinuclidine skeleton and the methylene bridge in between the two components has a hydroxyl group.
Quinoline derivatives [117] [118] Simple derivatives of quinoline derivatives of 2–quinolones and 4-quinolone: Anthranilic acid → 3-carboxyquinoline [119] Cusparine, echinopsine, evocarpine [118] [120] [121] Tricyclic terpenoids Flindersine [118] [122] Furanoquinoline derivatives Dictamnine, fagarine, skimmianine [118] [123] [124] Quinines
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Various substitutions made to the quinoline ring resulted in the development of numerous fluoroquinolone drugs. The addition of the fluorine atom at C-6 distinguishes the successive-generation fluoroquinolones from the first-generation quinolones, although examples are known that omit the atom while retaining antibacterial activity.
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