张心仪, 嵇汝运. 血吸虫病化学治疗的研究 ⅪⅤ.卤代二苯硫醚、卤代二苯亚砜及二苯硫醚Mannich碱的合成J. 药学学报, 1965, 12(10): 678-682.
引用本文: 张心仪, 嵇汝运. 血吸虫病化学治疗的研究 ⅪⅤ.卤代二苯硫醚、卤代二苯亚砜及二苯硫醚Mannich碱的合成J. 药学学报, 1965, 12(10): 678-682.
CHANG SING-NI KYI ZU-YOONG, . CHEMOTHERAPEUTIC STUDIES OF SCHISTOSOMIASIS——ⅪⅤ.SYNTHESIS OF SOME HALOGEN SUBSTITUTED DIPHENYL SULPHIDES AND SULPHOXIDES AND SOME MANNICH BASES DERIVED FROM DIPHENYL SULPHIDESJ. Acta Pharmaceutica Sinica, 1965, 12(10): 678-682.
Citation: CHANG SING-NI KYI ZU-YOONG, . CHEMOTHERAPEUTIC STUDIES OF SCHISTOSOMIASIS——ⅪⅤ.SYNTHESIS OF SOME HALOGEN SUBSTITUTED DIPHENYL SULPHIDES AND SULPHOXIDES AND SOME MANNICH BASES DERIVED FROM DIPHENYL SULPHIDESJ. Acta Pharmaceutica Sinica, 1965, 12(10): 678-682.

血吸虫病化学治疗的研究 ⅪⅤ.卤代二苯硫醚、卤代二苯亚砜及二苯硫醚Mannich碱的合成

CHEMOTHERAPEUTIC STUDIES OF SCHISTOSOMIASIS——ⅪⅤ.SYNTHESIS OF SOME HALOGEN SUBSTITUTED DIPHENYL SULPHIDES AND SULPHOXIDES AND SOME MANNICH BASES DERIVED FROM DIPHENYL SULPHIDES

  • 摘要: 鉴于2,2'-二羟基-3,3'-二溴代-5,5'-二氯代二苯硫醚(Ia,抗虫349)与2,2'-二羟基-3,3',5,5',6,6'-六氯代二苯硫醚(Ib抗虫390)对小白鼠体内的日本血吸虫具有明显的抑制与杀灭作用,乃合成一系列有关化合物。亚砜化合物(IIa、IIb)系由相应的硫醚(Ia、Ib)在冰醋酸中用过氧化氢氧化制成。2,2'-二羟基-4,4',5,5'-四氯代二苯硫醚(Id)用溴素溴化得化合物Ic。化合物Id-f系由苯环上带有相应取代基的苯酚与二氯化硫缩合而得。化合物Ig-o系由对位带有各种不同基因(Cl、Br、CH3等)的2,2'-二羟基二苯硫醚、甲醛与相应的仲胺在乙醇中进行Mannich反应而得。化合物Ia、Ib溶于苯中与无水(?)(?)嗪苯溶液作用分别得相应的(?)(?)嗪盐。动物试验结果指出2,2'-二羟基-3,3'-二溴代-4,4',5,5'-四氯代二苯硫醚(Ic,编号抗虫438)、2,2'-二羟基-3,3'-二溴代-5,5'-二氯代二苯亚砜(IIa,编号抗虫436)、2,2'-二羟基-3,3',5,5',6,6'-六氯代二苯亚砜(IIb,编号抗虫422)、以及2,2'-二羟基-3,3'-二溴代-5,5'-二氯代二苯硫醚、2,2'-二羟基-3,3',5,5',6,6'-六氯代二苯硫醚的(?)(?)嗪盐对小白鼠体内的日本血吸虫均有明显的抑制与杀灭作用,详细的药理结果将另文报导。

     

    Abstract: In view of the cffectivcness of bis(3,5,6-trichloro-2-hydroxyphenyl)-sulphide (Ib, CMS-390) and bis(3-bromo-5-chloro-2-hydroxyphenyl)sulphide(Ia, CMS-349) in the treatment of schistosomiasis japonicum, a series of analogous compounds was prepared in the present work for pharmacological examinations. The compounds I2 and Ib were oxidized with hydrogen peroxide, forming the corresponding sulphoxides (II2 and IIb). The compound substituted with mixed halogens (Ic) was prepared by bromination of the corresponding chloro-compound. When phenols with various substituents were reacted with sulphur chloride, the corresponding diphenyl sulphides were obtained. The Mannich bases were obtained by heating 2,2'-dihydroxydiphenyl sulphides with formaldehyde and secondary amines. The piperazine salts were prepared by coupling the corresponding diphenyl sulphides with anhydrous piperazine. Preliminary pharmacological examinations showed that bis (3-bromo-4,5-dichloro-2-hydroxyphenyl)-sulphide (Ic), bis (3-bromo-5-chloro- 2-hydroxyphenyl)-sulphoxide (II2), bis (3,5,6-trichloro-2-hydroxyphenyl)-sulphoxide (IIb) and the piperazine salt of bis(3-bromo-5-chloro-2-hydroxyphenyl-sulphide and bis(3,5,6- trichloro-2-hydroxyphenyl)-sulphde were quite effective against Schistosoma japonicum.

     

/

返回文章
返回