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

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Author

  • G Appendino
  • P Bettoni
  • A Noncovich
  • Olov Sterner
  • G Fontana
  • E Bombardelli
  • P Pera
  • R J Bernacki

Summary, in 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.

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 (ACS)

Topic

  • Organic Chemistry

Status

Published

ISBN/ISSN/Other

  • ISSN: 0163-3864