张心仪, 嵇汝运. 血吸虫病化学治疗的研究 ⅩⅢ.二苯硫醚类化合物的合成J. 药学学报, 1964, 11(1): 23-29.
引用本文: 张心仪, 嵇汝运. 血吸虫病化学治疗的研究 ⅩⅢ.二苯硫醚类化合物的合成J. 药学学报, 1964, 11(1): 23-29.
CHANG SING-NI KYI ZU-YOONG, . CHEMOTHERAPEUTIC STUDIES ON SCHISTOSOMIASIS——ⅩⅢ.SYNTHESIS OF SOME HALOGEN-SUBSTITUTED DIPHENYL SULPHIDESJ. Acta Pharmaceutica Sinica, 1964, 11(1): 23-29.
Citation: CHANG SING-NI KYI ZU-YOONG, . CHEMOTHERAPEUTIC STUDIES ON SCHISTOSOMIASIS——ⅩⅢ.SYNTHESIS OF SOME HALOGEN-SUBSTITUTED DIPHENYL SULPHIDESJ. Acta Pharmaceutica Sinica, 1964, 11(1): 23-29.

血吸虫病化学治疗的研究 ⅩⅢ.二苯硫醚类化合物的合成

CHEMOTHERAPEUTIC STUDIES ON SCHISTOSOMIASIS——ⅩⅢ.SYNTHESIS OF SOME HALOGEN-SUBSTITUTED DIPHENYL SULPHIDES

  • 摘要: 2,2′-二羟基-5,5′-二氯代二苯硫醚(Ⅱa)用次氯酸叔丁酯氯化,两个苯环中仅一个加上一个氯原子,成为三氯化合物(Ⅲ).Ⅱa及2,2′-二羟基-5,5′-二溴代二苯硫醚(Ⅴa)用N-溴代丁二酰亚胺溴化,两个苯环各加一个溴原子,成为二溴或四溴化合物(Ⅱc及Ⅴb)。2,2′-二羟基卤代二苯硫醚以乙酐及乙酸钠进行乙酰化,或以苯甲酰氯进行Schotten-Baumann反应,生成相应酯类;与碘甲烷、碘乙烷或2-二乙氨基氯乙烷分别制成相应醚类。动物试验结果2,2′-二羟基-3,3′,5,5′,6,6′-六氯代二苯硫醚(Ⅳa)对小白鼠体内的日本血吸虫具有明显的抑制与杀灭作用。2,2′-二羟基-3,3′-二溴代-5,5′-二氯代二苯硫醚(Ⅱc)亦有作用,但作用不及Ⅳa强。

     

    Abstract: In view of the effectiveness of bis(3,5-dichloro-2-hydroxyphenyl) sulphide (Bithionol, Ⅱb) in the treatment of human paragonimiasis and its protective action against the cercariae of Schistosoma mansoni, a series of analogous compounds was prepared in the present work for pharmacological examinations. 2,2'-Dihydroxy-5,5'-diphenyl sulphide (Ⅱa) was chlorinated by means of tert-butyl hypochlorite, or brominated by means of either bromine or N-bromosuccinimide, giving mono- or di-substituted derivatives. The compounds substituted with mixed halogens were prepared by bromination of the corresponding chloro-componnds. Many of such phenolic compounds were also acetylated, benzoylated or etherified, and compounds carrying various side chains of acyloxy, alkoxy or 2-diethylamino-ethoxy linkages were afforded. Since these compounds have a wide range of physico-chemical properties, it is expected that their pharmacodynamic properties would also be different. Preliminary pharmacological examinations revealed that bis (3,5,6-trichloro-2-hydroxyphenyl) sulphide (Ⅳa) was quite active against Schistosoma japonicum, and bis(3-bromo-5-chloro-2-hydroxyphenyl) sulphide (Ⅱc) was less active.

     

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