Selective phenolic acylation of 10-hydroxycamptothecin using poly (ethylene glycol) carboxylic acid

Bioorg Med Chem Lett. 2003 Feb 10;13(3):577-80. doi: 10.1016/s0960-894x(02)00926-5.

Abstract

Selective acylation of the phenolic hydroxyl group of 10-hydroxycamptothecin has been accomplished using phenyl dichlorophosphate. Additional modification of the 10-OH as an ether permits a 20-acyl derivative to be synthesized. This result along with data from a 6-hydroxyquinoline model strongly suggests that powerful intermolecular hydrogen bonding exists in the parent molecule.

MeSH terms

  • Acylation
  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacokinetics
  • Antineoplastic Agents / pharmacology
  • Camptothecin / analogs & derivatives*
  • Camptothecin / chemical synthesis*
  • Camptothecin / pharmacokinetics
  • Camptothecin / pharmacology
  • Carboxylic Acids / chemistry
  • Hydrogen Bonding
  • Hydroxyquinolines / chemistry
  • Indicators and Reagents
  • Leukemia P388 / drug therapy
  • Magnetic Resonance Spectroscopy
  • Neoplasms / drug therapy
  • Neoplasms / pathology
  • Polyethylene Glycols / chemistry
  • Rats
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Carboxylic Acids
  • Hydroxyquinolines
  • Indicators and Reagents
  • Polyethylene Glycols
  • 6-hydroxyquinoline
  • 10-hydroxycamptothecin
  • Camptothecin