Synthesis and in vitro antitumor activity of some amino-deoxy 7-hexofuranosylpyrrolo[2,3-d]pyrimidines

7-(6-amino-6-deoxy-β-d-glucofuranosyl)-5-cyanopyrrolo[2,3-d]pyrimidine (22) and 7-(3-aminomethyl-3-deoxy-β-d-allofuranosyl)-5-cyanopyrrolo[2,3-d]pyrimidine (28) were synthesized by sequentially coupling silylated 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine with the corresponding protected sugars 9 and 17, followed by deblocking and catalytic hydrogenation. Conversion of the 5-nitrile in 22 and 28 into a carboxamide gave the corresponding sangivamycin derivatives 23 and 29. Whereas 5′-aminomethyl nucleosides 22 and 23 inhibited the growth of four different human tumor cell lines at μM concentrations, the 3′-aminomethyl analogs 28 and 29 were much less active against these cells.