孙存济, 嵇汝运. 对羧甲巯基苯(月弟)化合物的制备J. 药学学报, 1959, 7(7): 266-269.
引用本文: 孙存济, 嵇汝运. 对羧甲巯基苯(月弟)化合物的制备J. 药学学报, 1959, 7(7): 266-269.
SUN TSUN-YSI KYI ZU-YOONG, . THE PREPARATION OF p-CARBOXYMETHYLMERCAPTOBENZE-NESTIBINOUS COMPOUNDSJ. Acta Pharmaceutica Sinica, 1959, 7(7): 266-269.
Citation: SUN TSUN-YSI KYI ZU-YOONG, . THE PREPARATION OF p-CARBOXYMETHYLMERCAPTOBENZE-NESTIBINOUS COMPOUNDSJ. Acta Pharmaceutica Sinica, 1959, 7(7): 266-269.

对羧甲巯基苯(月弟)化合物的制备

THE PREPARATION OF p-CARBOXYMETHYLMERCAPTOBENZE-NESTIBINOUS COMPOUNDS

  • 摘要: 对羧甲巯基苯胺重氮化后与新鲜制备的亚锑酸钠作用,生成对羧甲巯基苯(月弟)酸,再在醋酸溶液中与二氯化锡及盐酸作用,变为二氯化对羧甲巯基苯(月弟).后者与碘化钾作用成为相应二碘化合物,与氨水作用成为相应氧化物.二氯化对羧甲巯基苯(月弟)与巯基乙酸缩合成为二硫醇(月弟)盐,即双羧甲巯基(对羧甲巯基苯基)(月弟).后者在丙酮与水混合剂中热时失去—分子巯基乙酸,成为巯基乙酸对羧甲巯基苯(月弟).二氧化对羧甲巯基苯(月弟)与二巯基丙酸缩合则生成1-对羧甲巯基苯基-3-羧基-2,5-二硫间(月弟)五圜.

     

    Abstract: Prior work reported that p-carboxymethylmercaptobenzenestibonic acid was more active than tartar emetic against schistosomiasis japonica.Since it is generally believed that pentavalent antimo- ny compounds are reduced to trivalent ones by’a metabolic process,it would appear worth while to reduce this stibonic acid to the corresponding stibinous compounds and to examine their thera- peutic value. p-Carboxymethylmercaptoaniline was diazotized and then reacted with freshly prepared sodium antimonite,giving p-carboxymethylmercaptobenzenestibonic acid.Treatment of the latter compound with stannons chloride in concentrated hydrochloric acid medium caused the cleavage of the carbon- antimony bond,and phenylmercaptoacetic acid was isolated.If the reduction,however,was carried out in acetic acid medium at-3°in the presence of small quantity of hydrochloric acid,p-carboxy- methylmercaptostibinous chloride was afforded.The latter gave the corresponding stibinous iodide and stibinous oxide on treatment with potassium iodide or ammonia respectively. p-Carboxymethylmercaptobenzenestibinous chloride readily reacted with thioglycollic acid in the presence of sodium bicarbonate,forming a dimercaptide,bis-carboxymethylmercapto-(p-carboxymethyl- mercaptophenyl)-stibine.On heating of the latter compound in aqueous acetone one mole of thio- glycollic acid was readily eliminated,and a chelating salt p-carboxymethylmercaptobenzenestibinous thioglycollate was formed.Condensation of p-carboxymethylmercaptobenzenestibinous chloride with dimercaptopropionic acid gave 1-p-carboxymethylmercaptophenyl-3-carboxyl-2,5-dithia-1-stibia-cyclo- pentane.

     

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