Structure-activity relationships of ring C-secotaxoids. 1. Acylative modifications.
- Published Article
Journal of natural products
- Publication Date
Feb 01, 2004
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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The corresponding record at NLM can be accessed at https://www.ncbi.nlm.nih.gov/pubmed/14987056