SAR of Dibenzazepines

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Chapter: Medicinal Chemistry : Antidepressants

Maximum potency occurs when the basic nitrogen is separated from tricyclic nucleus by a propylene bridge.


SAR of Dibenzazepines



Variation in the side chain

  • Maximum potency occurs when the basic nitrogen is separated from tricyclic nucleus by a propylene bridge.

  • Ethylene in between ring and side chain ‘N’ atom gives significant activity.

  • Increase in the ‘C’ length from propylene leads to it becoming ineffective or produce toxic effects.

  • Branching does not affect the activity. For example, Imipramine and Trimipramine have same activity.

  • A carbonyl functionality in position 1 of the propyl side chain of imipramine have antidepressant like activity.

  • Side chain with quinuclidine, morpholine nuclei claimed to be potent.

• The tertiary amine and secondary amine in the side chain are important because they significantly affect both the monoamine reuptake activity as well as interaction with other receptors. For example, tertiary amines are more potent inhibitors of 5-HT reuptake, while secondary amines are more potent in their inhibition of NE reuptake. Tertiary amines also have more potent activity to α1 adrenergic, muscarnic, and histaminic receptors.


Variation in the ring substituents

  • Presence of chloro-substituent at C-3 is less active than imipramine.

  • Presence of dimethyl or keto at C-10 leads to the compounds becoming ineffective.

  • Placement of methyl group at 2,8 position or chloro group at 3,7 resulted in compounds becoming ineffective.


Variation in the ring system

  • Iminostilbenes are equally active.

  • Piperazinyl derivatives are ineffective.


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