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Synthesis of 1‐methyl‐ and 1‐ethoxycarbonyl‐2‐phenylcarbamoylpiperidazines as potential anticonvulsant agents
Author(s) -
Kornet Milton J.,
Chu John
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180213
Subject(s) - chemistry , pentylenetetrazol , anticonvulsant , seizure threshold , aryl , aluminum hydride , lithium (medication) , medicinal chemistry , organic chemistry , epilepsy , catalysis , medicine , alkyl , neuroscience , biology , endocrinology , methoxide
1‐Methyl‐ and 1‐ethoxycarbonyl‐2‐phenylcarbamoylpiperidazines were synthesized and examined for anticonvulsant activity in the maximal electroshock seizure and pentylenetetrazol seizure threshold tests. One synthetic pathway for the 1‐methyl compounds involved the reaction between aryl isocyanates and 1‐methyl‐piperidazine. A second procedure, of lesser utility, utilized selective lithium aluminum hydride reduction of 1‐ethoxycarbonyl‐2‐phenylcarbamoylpiperidazines and gave the corresponding 1‐methyl compounds. The 1‐ethoxycarbonyl series was obtained from aryl isocyanates and 1‐ethoxycarbonylpiperidazine. Several 1‐methyl‐2‐phenylcarbamoylpiperidazines exhibited significant anticonvulsant activity.