宗汝实, 嵇汝运. 一些具有局部麻醉作用的哌啶基酰基苯胺的合成J. 药学学报, 1963, 10(4): 219-224.
引用本文: 宗汝实, 嵇汝运. 一些具有局部麻醉作用的哌啶基酰基苯胺的合成J. 药学学报, 1963, 10(4): 219-224.
TSUNG JU-SHIH AND KYI ZU-YOONG, . THE SYNTHESIS OF SOME PIPERIDINO-ACYL ANILIDES WITH MARKED LOCAL ANESTHETIC ACTIVITYJ. Acta Pharmaceutica Sinica, 1963, 10(4): 219-224.
Citation: TSUNG JU-SHIH AND KYI ZU-YOONG, . THE SYNTHESIS OF SOME PIPERIDINO-ACYL ANILIDES WITH MARKED LOCAL ANESTHETIC ACTIVITYJ. Acta Pharmaceutica Sinica, 1963, 10(4): 219-224.

一些具有局部麻醉作用的哌啶基酰基苯胺的合成

THE SYNTHESIS OF SOME PIPERIDINO-ACYL ANILIDES WITH MARKED LOCAL ANESTHETIC ACTIVITY

  • 摘要: N-(β-苯硫乙基)-苯胺和N-(β-对氯苯硫乙基)-苯胺分别用氯乙酰氯、β-氯丙酰氯和γ-氯丁酰氯酰化,生成的氯代酰胺(IIIa-e)用哌啶处理,得到一系列N-(β-苯硫乙基)-哌啶基酰基苯胺(IVa-c)和N-(β-对氯苯硫乙基)-哌啶基酰基苯胺(IVd,e).药理试验表明化合物IVa—e有很强的局部麻醉作用.

     

    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.

     

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