4-Substituted Quinolines: Structure Activity Relationship

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Chapter: Medicinal Chemistry : Antimalarials

At C-4 position, the dialkylaminoalkyl side chain has 2-5 carbon atoms between the nitrogen atoms, particularly the 4-diethylaminomethyl butyl amino side chain that is optimal for activity, as in chloroquine and quinacrine.


STRUCTURE–ACTIVITY RELATIONSHIP


·At C-4 position, the dialkylaminoalkyl side chain has 2-5 carbon atoms between the nitrogen atoms, particularly the 4-diethylaminomethyl butyl amino side chain that is optimal for activity, as in chloroquine and quinacrine.

·The substitution of a hydroxyl group on one of the ethyl groups on the tertiary amine (hydroxyl quinoline), reduces toxicity.

·Incorporation of an aromatic ring in the side chain (e.g. amodiaquine) gives a compound with reduced toxicity and activity.

·The tertiary amine in the side chain is important.

·The introduction of an unsaturated bond in the side chain was not detrimental to activity.

·The 7-chloro group in the quinoline nucleus is optimal, the methyl group in position 3 reduces activity, and an additional methyl group in position 8 abolishes activity.

·The D-isomer of chloroquine is less toxic than its L-isomer.

 

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