Structure-activity relationship in carbanilic acid derivatives.
The paper presents a survey of the relationship in carbanilic acid derivatives between structure and local anaesthetic activity. By modifying the three parts of a typical local anaesthetic, i.e., the aromatic (lipophilic) part, the intermediate chain and the basic (hydrophilic) part, substances with high local anaesthetic activity have been obtained. The derivatives with alkoxy substituents with 5-7 carbon atoms in the ortho and meta positions have proved advantageous. The local anaesthetic activity is significantly influenced by the basic part, usually formed by secondary or tertiary amines, and particularly by the structure of the intermediate chain. Significant differences have been found to exist between the activity of individual geometrically, optically and conformationally fixed isomers. The results indicate that in the carbanilic acid derivatives studied, local anaesthetic activity depends on their structural arrangement and physicochemical properties, which have been found to play an important role regarding the presumed non-specific effect of these substances.
D000779:Anesthetics, Local / Q000494:pharmacology*; D000818:Animals; D002219:Carbamates / Q000494:pharmacology*; D002462:Cell Membrane / Q000187:drug effects*; D055598:Chemical Phenomena; D002621:Chemistry; D006801:Humans; D013329:Structure-Activity Relationship
D000779:Anesthetics, Local; D002219:Carbamates