New highly active taxoids from 9beta-dihydrobaccatin-9,10-acetals. Part 2

Bioorg Med Chem Lett. 2002 Oct 21;12(20):2815-9. doi: 10.1016/s0960-894x(02)00628-5.

Abstract

To investigate structure-activity relationships of the 9,10-acetal-9beta-dihydro taxoids, we modified the 7-hydroxyl groups of the 9,10-acetonide-3'-(4-pyridyl) analogue to deoxy, methoxy, alpha-F, and 7beta,8beta-methano group. As a result of this study, we found that the 7-deoxy analogue was the strongest among these analogues. In addition, we found that the 7-deoxy-3'-(4-pyridyl) and 7-deoxy-3'-(2-pyridyl) analogues showed stronger activity against cell lines expressing P-glycoprotein than the corresponding 3'-phenyl analogue.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Bridged-Ring Compounds / chemistry
  • Chemical Phenomena
  • Chemistry, Physical
  • Chromatography, High Pressure Liquid
  • Drug Screening Assays, Antitumor
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Paclitaxel / analogs & derivatives*
  • Paclitaxel / chemical synthesis
  • Paclitaxel / pharmacology*
  • Solubility
  • Stereoisomerism
  • Structure-Activity Relationship
  • Taxoids*
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents, Phytogenic
  • Bridged-Ring Compounds
  • Indicators and Reagents
  • Taxoids
  • taxane
  • Paclitaxel