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

Authors
  • Appendino, Giovanni
  • Bettoni, Piergiorgio
  • Noncovich, Alain
  • Sterner, Olov
  • Fontana, Gabriele
  • Bombardelli, Ezio
  • Pera, Paula
  • Bernacki, Ralph J
Type
Published Article
Journal
Journal of natural products
Publication Date
Feb 01, 2004
Volume
67
Issue
2
Pages
184–188
Identifiers
PMID: 14987056
Source
Medline
License
Unknown

Abstract

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.

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