Synthesis and antileukemic activity of chymotrygsin-activated derivatives of 3'-amino-2',3'-dideoxycytidine. (Synthetic nucleosides and nucleotides. XXXIII

Article abstract of DOI:10.1248/cpb.43.501

3'-Amino-2',3'-dideoxycytidine (8) was directly synthesized from 2'-deoxycytidine, 2',3'-Dideoxy-3'-(N-acyl-L-phenylalanylamino)cytidines (acyl =butoxycarbonyl (9a), acetyl (9b), benzoyl (9c), and α-hexanoyl (9d)) were synthesized as chymotrypsin-activated prodrugs of 8. This N-protection was required for activation by chymotrypsin to 8. In vitro, compound 8 showed high cytotoxic activity against P388 cells, but the prodrugs 9a-d were ineffective. In vitro, however, these prodrugs showed much higher activity than 8 in mice bearing P388 cells.

Full text of DOI:10.1248/cpb.43.501

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