ALKYLATING NUCLEOSIDES .1. SYNTHESIS AND CYTOSTATIC ACTIVITY OF N-GLYCOSYL(HALOMETHYL)-1,2,3-TRIAZOLES - NEW TYPE OF ALKYLATING AGENT

1, 3-Dipolar cycloaddition of benzyl azide or peraeetylaced glucopyranosyl azides to propargyl halides or 1, 4-di-halobutynes yielded 1-benzyl-or l-glycosyl(halomethyl)-l, 2, 3-triazoIes. Alkylating chloromethyl-bromomethyl-and iodomethyl-l, 2, 3-triazoles were also obtained from the corresponding hydroxymethyl derivatives by treatment with (C6H5)3P/CCl4, (C6H50)3P/Br2 and (C6HsO)3P/I2, respectively. l-Benzyl-4-(fluoromethyl)-l, 2, 3-triazole was obtained from l-benzyi-4-(bromomethyl)-l, 2, 3-triazole by treatment with KF and 18-crown-6. Chloromethyl-,bromomethyl-, and iodomethyl-l, 2, 3-triazole derivatives inhibited the —in vitro– growth of HeLa cells. Some of these compounds increased the life span of mice bearing tumors. © 1979, American Chemical Society. All rights reserved.