Javascript is not activated in your browser. This website needs javascript activated to work properly.
You are here

Structure-activity relationships of ring C-secotaxoids. 1. Acylative modifications

  • G Appendino
  • P Bettoni
  • A Noncovich
  • Olov Sterner
  • G Fontana
  • E Bombardelli
  • P Pera
  • R J Bernacki
Publishing year: 2004
Language: English
Pages: 184-188
Publication/Series: Journal of Natural Products
Volume: 67
Issue: 2
Document type: Journal article
Publisher: The American Chemical Society

Abstract english

The acylative modification of IDN 5390 (3a), a 7,8-secotaxoid under preclinical development, was investigated. A modest decrease of potency was observed upon acylation of the primary and the enolic hydroxyls, suggesting that, just like in paclitaxel, the hydroxyl groups in the upper right-hand sector are not critical for cytotoxicity. The activity of these analogues, and especially of the chemically robust carbonates 3c and 3d, makes it unlikely that the activity of IDN 5390 is due to in vivo oxidation to a fledgling 7-aldehyde and re-aldolization to the corresponding taxane derivative.


  • Organic Chemistry


  • ISSN: 0163-3864
Olov Sterner
E-mail: olov [dot] sterner [at] chem [dot] lu [dot] se


Centre for Analysis and Synthesis

+46 70 530 66 49