Abstract:
In a previous paper, it was reported by the present authors that certain N-
β-(
p-chlorophenylmercapto)-ethyl-
β'-dialkylaminopropionanilides were found to have pronounced local anesthetic activity, the most potent one, N-
β-(
p-chlorophenylmercapto)-ethyl-
β'-piperidino-propionanilide, being comparable to cinchocaine in potency. In the present work, a series of N-(
β-phenylmercaptoethyl) and N-
β-(
p-chlorophenylmercapto)-ethyl-
β'-piperidino-acyl anilides has been synthesized to see whether more potent local anesthetics could be found. N-(
β-phenylmercaptoethyl)-aniline and N-
β-(
p-chlorophenylmercapto)-ethyl-aniline were acylated with chloroacetyl chloride,
β-chloropropionyl chloride or
γ-chlorobutyryl chloride respectively. The desired compounds (IVa—e) were obtained by treating the chloroamides thus formed (IIIa—e) with piperidine. Pharmacological examinations revealed that compounds IVa—e had marked local anesthetic activity but none were as active as cinchocaine. The chloroamides IIIa—f which bear some structural relationship to the anticonvulsant hibicon (V) proved to be devoid of anticonvulsant activity.