Abstract
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 C2 (III) and C4 (II), and of two C1 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 C2 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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