L-Chlorozotocin.

Abstract

L-Chlorozotocin (2-[[[2-chloroethyl)nitrosoamino]carbonyl]amino]-2-deoxy-L-glucose) was synthesized in seven steps from L-arabinose for comparison with chlorozotocin, which is the D enantiomorph and an antineoplastic agent with clinical potential. Purification of the intermediate 2-amino-2-deoxy-L-glucose as the Schiff's base formed with 4-methoxybenzaldehyde ensured complete separation from the manno epimer. Comparative screening against leukemia L1210 with concurrent toxicity controls revealed no significant difference between D- and L-chlorozotocin in either activity or toxicity.

• Authors: T P Johnston, G S McCaleb, T Anderson, D S Murinson
• Journal: Journal of medicinal chemistry (J Med Chem) Vol. 22 Issue 5 Pg. 597-9 (May 1979) ISSN: 0022-2623 [Print] United States
• PMID: 156793 (Publication Type: Journal Article, Research Support, U.S. Gov't, P.H.S.)

Chemical References

• DNA, Neoplasm
• chlorozotocin
• Streptozocin

Topics

• Animals
• Bone Marrow (drug effects, metabolism)
• DNA, Neoplasm (biosynthesis)
• Leukemia L1210 (drug therapy, metabolism)
• Male
• Mice
• Stereoisomerism
• Streptozocin (analogs & derivatives, chemical synthesis, pharmacology)