2-(3-Amino-3-deoxy-beta-D-xylofuranosyl)thiazole-4-carboxamide: a new tiazofurin analogue with potent antitumour activity

Bioorg Med Chem Lett. 2006 Oct 15;16(20):5317-20. doi: 10.1016/j.bmcl.2006.07.086.

Abstract

A new tiazofurin analogue, 2-(3-amino-3-deoxy-beta-d-xylofuranosyl)thiazole-4-carboxamide (3), was synthesized starting from d-glucose and evaluated for its in vitro antiproliferative activity against a panel of human tumour cell lines. Compound 3 exhibited the most powerful cytotoxicity against K562 cells, being approximately 100-fold more potent than tiazofurin. This analogue was also active against Jurkat, HT-29 and HeLa malignant cells, with respective IC(50) values being ca. 2-, 27- and 17-fold lower than those observed for tiazofurin. Remarkably, compound 3 did not exhibit any significant cytotoxicity towards normal foetal lung MRC-5 cell line.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • Humans
  • In Vitro Techniques
  • Molecular Conformation
  • Ribavirin / analogs & derivatives*
  • Ribavirin / chemical synthesis
  • Ribavirin / chemistry
  • Ribavirin / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry
  • Thiazoles / pharmacology*

Substances

  • 2-(3-amino-3-deoxyxylofuranosyl)thiazole-4-carboxamide
  • Antineoplastic Agents
  • Thiazoles
  • Ribavirin
  • tiazofurin