Oxindole-3-spiropyrrolidines and -piperidines. Synthesis and local anesthetic activity.
The synthesis and local anesthetic properties of five 1-dealkyloxindole-3-spiropyrrolidines and six 1-dealkyloxindole-3-spiropiperidines are described. The compounds studied include members of all five possible positional isomers of the two classes of spirooxindoles; all showed local anesthetic activity by the rat sciatic nerve block method. The coincidence of the least variability in the relative positions of basic nitrogen, amide carbonyl, and aromatic ring (compounds 1 and 6) with lowest normalized toxicity is noteworthy.
D000779:Anesthetics, Local / Q000138:chemical synthesis* / Q000633:toxicity; D000818:Animals; D007211:Indoles / Q000138:chemical synthesis / Q000494:pharmacology / Q000633:toxicity; D007928:Lethal Dose 50; D009407:Nerve Block; D010880:Piperidines / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D051381:Rats; D012584:Sciatic Nerve / Q000187:drug effects; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000494:pharmacology / Q000633:toxicity
D000779:Anesthetics, Local; D007211:Indoles; D010880:Piperidines; D011759:Pyrrolidines; D013141:Spiro Compounds