The ring-expanded nucleoside 4,6-diamino-8-imino-8H-1-�-D-ribofuranosyl imidazo[4,5-e][1,3]diazepine(1) exhibited potent broad spectrum anticancer activities in vitro against a wide variety of human tumor cell lines. The heterocyclic aglycon of this nucleoside with a long C18 alkyl attached to 6-amino position (2;R=C18 alkyl, R'=H) was also found to exhibit potent in vitro anti-cancer activity against prostate, breast, ovarian and lung cancers. Based on this prototype structure, and as part of the SAR studies, a series of heterocyclic bases containing 5:7 fused imidazo[4,5-e][1,3]diazepine ring system were synthesized with various alkyl and aralkyl functionalities at the 6-amino position and with a benzyl or substituted benzyl group at the imidazole N-1 position. Synthesis and anticancer activities of the title compounds will be presented.

Synthesis and biological activity of a series of ring-expanded heterocyclic bases containing the 5:7-fused imidazo[4,5-<i>e</i>][1,3]diazepine ring system as potent anti-cancer agents

240th National Meeting (2010)

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Synthesis and biological activity of a series of ring-expanded heterocyclic bases containing the 5:7-fused imidazo[4,5-e][1,3]diazepine ring system as potent anti-cancer agents