Synthesis and antitumour activity of a new series of nitrosoureido sugars

Eur J Med Chem. 2000 Jan;35(1):137-46. doi: 10.1016/s0223-5234(00)00114-8.

Abstract

New nitrosoureido derivatives of di- or tri-deoxy-sugars have been synthesized. Very potent antitumour activity against L1210 leukaemia was exhibited by the compounds derived from methyl 3-amino-3, 4-dideoxy-beta- and alpha- and 4-amino-2,4-dideoxy-beta- and alpha-D-arabino-hexopyranosides, 24, 26, 28 and 29, respectively. In further evaluation against B16 melanocarcinoma bearing mice, only compounds 24 and 26 displayed significant activity. Owing to its lower acute toxicity, methyl 3-[3-(2-chloroethyl)-3-nitrosoureido]-3, 4-dideoxy-beta-D-arabino-hexopyranoside 24 appeared as the best candidate for preclinical studies.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / therapeutic use*
  • Carmustine / therapeutic use
  • Glucosides / chemical synthesis*
  • Glucosides / therapeutic use*
  • Leukemia L1210 / drug therapy
  • Melanoma, Experimental / drug therapy
  • Mice
  • Mice, Inbred C57BL
  • Molecular Structure
  • Nitrosourea Compounds / chemical synthesis*
  • Nitrosourea Compounds / therapeutic use*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Glucosides
  • Nitrosourea Compounds
  • methyl 3,4-dideoxy-3-(2-chloroethyl)nitrosoureidoglucoside
  • Carmustine