Orally active docetaxel analogue: synthesis of 10-deoxy-10-C-morpholinoethyl docetaxel analogues

Bioorg Med Chem Lett. 2001 Feb 12;11(3):407-10. doi: 10.1016/s0960-894x(00)00682-x.

Abstract

To improve cytotoxicity of 10-deoxy-10-C-morpholinoethyl docetaxel analogues against various tumor cell lines including resistant cells expressing P-glycoprotein (P-gp), we modified the 7-hydroxyl group to hydrophobic groups (methoxy, deoxy, 6,7-olefin, alpha-F, 7-beta-8-beta-methano, fluoromethoxy). Among these analogues, the 7-methoxy analogue showed the strongest cytotoxicity. This analogue showed potent activity against B16 melanoma BL6 in vivo by oral administration.

MeSH terms

  • Administration, Oral
  • Animals
  • Antineoplastic Agents, Phytogenic / administration & dosage
  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Cell Division / drug effects
  • Combinatorial Chemistry Techniques
  • Docetaxel
  • Drug Screening Assays, Antitumor
  • Humans
  • Inhibitory Concentration 50
  • Lung Neoplasms / drug therapy
  • Lung Neoplasms / pathology
  • Melanoma, Experimental / drug therapy
  • Mice
  • Mice, Inbred C57BL
  • Morpholines / administration & dosage
  • Morpholines / chemical synthesis
  • Morpholines / pharmacology*
  • Paclitaxel / administration & dosage
  • Paclitaxel / analogs & derivatives*
  • Paclitaxel / chemical synthesis
  • Paclitaxel / pharmacology*
  • Solubility
  • Structure-Activity Relationship
  • Survival Rate
  • Taxoids*
  • Tumor Cells, Cultured / drug effects

Substances

  • 10-deoxy-10-C-morpholinoethyl docetaxel
  • Antineoplastic Agents, Phytogenic
  • Morpholines
  • Taxoids
  • Docetaxel
  • Paclitaxel