高怡生, 徐修容, 李志毅, 周祖德, 邓蓉仙, 苏镜娱, 吴淑云. 肿瘤的化学治疗 Ⅳ.若干芳香脂肪硝基醇及β-硝基苯乙烯类化合物的合成及其体外抗肿瘤作用J. 药学学报, 1960, 8(2): 70-76.
引用本文: 高怡生, 徐修容, 李志毅, 周祖德, 邓蓉仙, 苏镜娱, 吴淑云. 肿瘤的化学治疗 Ⅳ.若干芳香脂肪硝基醇及β-硝基苯乙烯类化合物的合成及其体外抗肿瘤作用J. 药学学报, 1960, 8(2): 70-76.
KAO YEE-SHENG, HSU HSIU-YONG, LEE TZE-NEE, CHOU TSU-TEH, DENG YONC-SIEN, SOO CHIN-YU, AND WU SHU-YUN. TUMOUR CHEMOTHERAPY——IV.SYNTHESIS OF SOME ARYLALIPHATIC NITROALCOHOLS AND NITROSTYRENES AND THEIR IN VITRO ANTITUMOUR ACTIVITYJ. Acta Pharmaceutica Sinica, 1960, 8(2): 70-76.
Citation: KAO YEE-SHENG, HSU HSIU-YONG, LEE TZE-NEE, CHOU TSU-TEH, DENG YONC-SIEN, SOO CHIN-YU, AND WU SHU-YUN. TUMOUR CHEMOTHERAPY——IV.SYNTHESIS OF SOME ARYLALIPHATIC NITROALCOHOLS AND NITROSTYRENES AND THEIR IN VITRO ANTITUMOUR ACTIVITYJ. Acta Pharmaceutica Sinica, 1960, 8(2): 70-76.

肿瘤的化学治疗 Ⅳ.若干芳香脂肪硝基醇及β-硝基苯乙烯类化合物的合成及其体外抗肿瘤作用

TUMOUR CHEMOTHERAPY——IV.SYNTHESIS OF SOME ARYLALIPHATIC NITROALCOHOLS AND NITROSTYRENES AND THEIR IN VITRO ANTITUMOUR ACTIVITY

  • 摘要: 1.試驗了α-二氯乙酰胺(或乙酰胺基)-β-羥基-对-硝基-邻羥基(或甲氧基)苯丙酮及其相当的氨基化合物的体外抗艾氏腹水瘤細胞的作用,表示硝基对产生活力有影响。2.合成了若干芳香脂肪硝基化合物及β-硝基苯乙烯类化合物,并試驗了該項化合物的体外抗艾氏腹水瘤細胞的活力。3.从活力与化学結构的关系看,脂肪族飽和碳原子上的硝基对产生抗瘤細胞活力无影响,而硝基連在不飽和碳原子上时对活力的增強有很大关系。故一系列的β-硝基苯乙烯类化合物均有相当好的抗肿瘤細胞作用。至于苯乙烯环上的取代基則关系不大,除非取代的基团体积較大,活力也减小。

     

    Abstract: In view of some analogues of chloramphenicol show more or less in vitro activity towards quite a few species of tumour cells,the authours have examined the in vitro anti-Ehrlich ascites activity of 5 compounds prepared by one of us and Par before,namely,α-dichloroacetamido- (or acetamido)-β-hydroxy-p-nitro-o-hyrdroxy-(or methoxy)-propiophenone(Ⅰ,Ⅱ,Ⅲ),and α-dichloro- acetamido-β-hydroxy-p-amino-o-hydroxy-propiophenone(IV, V).The results(see Tab. 1)showed that the compounds carrying a nitro group in the benzene ring possessed invariably higher activity as compared with their corresponding amino analogues.Therefore,it appears that the nitro group attached to benzene ring plays somewhat important role in producing the in vitro anti-Ehrlich ascites activity. These facts led us to prepare some arylaliphatic nitroalcohols(Ⅶ,Ⅸ,Ⅹ,Ⅺ)and some derivatives of β-nitrostyrenes (Ⅻ, ⅩⅣ,ⅩⅤ,ⅩⅥ,ⅩⅦ,ⅩⅧ,ⅩⅨ,ⅩⅩ) for the purpose of examining their anti-Ehrlich ascites activity.The results(see Tab.2)showed that the nitro group attached to saturated aliphatic carbon atom has no obvious influence in enhancing the anti-tumour activity,in some cases even with counter effect,but that which attached to unsaturated aliphatic carbon atom,as in the case of a series of β-nitrostyrene derivatives,did show higher activity.Therefore, the phenomenon is in harmony with the result described for I,II in the foregoing paragraph,that is,nitro group attached to unsaturated carbon atom is equivalent to that attached to benzene ring. 1-Phenyl-4-nitrobutadiene(ⅩⅥ),in which the nitro group being in the vinylogous position of β-nitrostyrene,also possessed considerable activity.The groups,except that with greater molar volume,substituted in'the benzene nucleus of β-nitrostyrene appear to have no significant influ- ence. The m.ps.of the compounds prepared are recorded in Tab.2.

     

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