SYNTHESIS AND IN-VITRO ANTITUMOR-ACTIVITY OF SOME AMINO-DEOXY 7-HEXOFURANOSYLPYRROLO[2,3-D]PYRIMIDINES

-D-glucofuranosyl)-5-cyanopyrrolo[2,3-d]pyrimidine (22) and ethyl-3-de oxy-beta-D-allofuranosyl)-5-cyanopyrrolo [2,3-d]pyrimidine (28) were s ynthesized by sequentially coupling silylated 4-amino-6-bromo-5-cyanop yrrolo[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 s angivamycin derivatives 23 and 29. Whereas 5'-aminomethyl nucleosides 22 and 23 inhibited the growth of four different human tumor cell line s at mu M concentrations, the 3'-aminomethyl analogs 28 and 29 were mu ch less active against these cells. (C) 1998 Elsevier Science Ltd. All rights reserved.