Heteroaromatic Taxol Analogues: The Chemistry and Biological Activities of 3′-Furyl and 3′-Pyridyl Substituted Taxanes

Gunda I. Georg, Gerlandine C B Harriman, Michael Hepperle, Richard H. Himes

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

A series of novel heterocyclic taxol analogues has been synthesized utilizing 2-azetidinones derived from the ester enolate-imine cyclocondensation. 2-Azetidinones possessing stereochemistry complementary to that of taxol's phenylisoserine side chain were synthesized in fair to high enantiomeric purity utilizing the chiral glycolate derived from Oppolzer's chiral auxiliary and the appropriate N-trimethylsilylaldimines. These novel analogues were evaluated in the microtubule assembly assay as well as tested for cytotoxicity against B16 melanoma cells. The 2-furyl analoug e29 proved to be more active than the parent, taxol.

Original languageEnglish (US)
Pages (from-to)1381-1384
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume4
Issue number11
DOIs
StatePublished - Jun 9 1994

Fingerprint

Dive into the research topics of 'Heteroaromatic Taxol Analogues: The Chemistry and Biological Activities of 3′-Furyl and 3′-Pyridyl Substituted Taxanes'. Together they form a unique fingerprint.

Cite this