Preparation of phenolic paclitaxel metabolites

H Park; M Hepperle; T C Boge; R H Himes; G I Georg

doi:10.1021/jm960142x

Preparation of phenolic paclitaxel metabolites

J Med Chem. 1996 Jul 5;39(14):2705-9. doi: 10.1021/jm960142x.

Authors

H Park¹, M Hepperle, T C Boge, R H Himes, G I Georg

Affiliation

¹ Department of Medicinal Chemistry, University of Kansas, Lawrence 66045, USA.

PMID: 8709100
DOI: 10.1021/jm960142x

Abstract

The synthesis and biological evaluation of the two known phenolic metabolites of paclitaxel are described. The C3'-phenolic metabolite 2 of paclitaxel was prepared from 7-(triethylsilyl)-baccatin III (8) and enantioenriched N-benzoyl-2-azetidinone 7. The C2-phenolic metabolite 3 was synthesized from paclitaxel (1a) via selective C2 debenzoylation and reacylation.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Antineoplastic Agents, Phytogenic / chemical synthesis*
Antineoplastic Agents, Phytogenic / pharmacology
Molecular Structure
Paclitaxel / chemistry
Paclitaxel / metabolism*
Phenol
Phenols / metabolism*
Tubulin / drug effects
Tumor Cells, Cultured

Substances

Antineoplastic Agents, Phytogenic
Phenols
Tubulin
Phenol
Paclitaxel