Structure-activity relationships of ring C-secotaxoids. 1. Acylative modifications
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/285094
- author
- Appendino, G ; Bettoni, P ; Noncovich, A ; Sterner, Olov LU ; Fontana, G ; Bombardelli, E ; Pera, P and Bernacki, R J
- organization
- publishing date
- 2004
- 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 (ACS)
- external identifiers
-
- pmid:14987056
- wos:000220023300012
- scopus:1442310137
- ISSN
- 0163-3864
- DOI
- 10.1021/np0303456
- language
- English
- LU publication?
- yes
- additional info
- The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
- id
- 02ce6ea8-6458-4f7c-9cc7-57205e185bbe (old id 285094)
- date added to LUP
- 2016-04-01 15:24:00
- date last changed
- 2022-03-30 01:09:42
@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 (ACS)}}, series = {{Journal of Natural Products}}, title = {{Structure-activity relationships of ring C-secotaxoids. 1. Acylative modifications}}, url = {{http://dx.doi.org/10.1021/np0303456}}, doi = {{10.1021/np0303456}}, volume = {{67}}, year = {{2004}}, }