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

Appendino, G; Bettoni, P; Noncovich, A; Sterner, Olov LU ; Fontana, G; Bombardelli, E; Pera, P and Bernacki, R J (2004) In Journal of Natural Products 67(2). p.184-188
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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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Natural Products
volume
67
issue
2
pages
184 - 188
publisher
The American Chemical Society
external identifiers
  • pmid:14987056
  • wos:000220023300012
  • scopus:1442310137
ISSN
0163-3864
DOI
10.1021/np0303456
language
English
LU publication?
yes
id
02ce6ea8-6458-4f7c-9cc7-57205e185bbe (old id 285094)
date added to LUP
2007-10-16 13:20:04
date last changed
2017-01-01 06:38:53
@article{02ce6ea8-6458-4f7c-9cc7-57205e185bbe,
  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.},
  author       = {Appendino, G and Bettoni, P and Noncovich, A and Sterner, Olov and Fontana, G and Bombardelli, E and Pera, P and Bernacki, R J},
  issn         = {0163-3864},
  language     = {eng},
  number       = {2},
  pages        = {184--188},
  publisher    = {The American Chemical Society},
  series       = {Journal of Natural Products},
  title        = {Structure-activity relationships of ring C-secotaxoids. 1. Acylative modifications},
  url          = {http://dx.doi.org/10.1021/np0303456},
  volume       = {67},
  year         = {2004},
}