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.
Several 2‐aryl‐3,4‐dialkyltetrahydro‐1,3,4‐oxadiazines have been synthesized from 2‐(1,2‐dialkylhydrazino)ethanol (2) and aromatic aldehydes. Also, three 2‐aryl‐3,4‐dialkyltetrahydro‐1,3,4‐oxadiazin‐5‐ones were obtained from the reaction of 1,2‐dialkylglycolylhydrazine (5) and aromatic aldehydes. These compounds exhibited activity in the maximal electroshock seizure test.
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