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

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.