The α- and β-methyl glycosides (
IV and
V, respectively) of the antibiotic streptozotocin (
I) have been synthesized. In addition, analogs involving epimeric changes at C
2 (
III) and C
4 (
II), and of two C
1 analogs, 3-β-Dglucopyranosyl-1-methyl-1-nitrosourea (
XXIII) and the corresponding D-galactopyranosyl compound (
XXV), together with their tetra-O-acetates (
XXII and
XXIV, respectively) have been prepared. An open-chain analog was obtained by the synthesis of 1-deoxy-1-(3-methyl-3-nitrosoureido)-D-glucitol (
XXIX), but the 2-deoxy-D-glucitol derivative (
XXVII) decomposed on attempted isolation. Epimerization at C
2 reduces the antibacterial activity markedly; all other changes made destroy it. All of the analogs show cytotoxic activity in the range of streptozotocin or higher, and all are devoid of diabetogenicity.
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