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Enantiomeric Derivatives of Tokinolide B: Absolute Configuration and Biological Properties

Leon, Alejandra; Antonio Cogordan, J.; Sterner, Olov LU and Delgado, Guillermo (2012) In Journal of Natural Products 75(5). p.859-864
Abstract
The enantiomeric lactams (-)-8, (+)-8, (+)-9, and (-)-9 were formed by the reaction of the dimeric phthalide rac-tokinolide B (rac-3) with (R)-(+)-alpha-methylbenzylamine and (S)-(-)-alpha-methylbenzylamine. The absolute configurations of compounds 8 and 9 were assigned by experimental and theoretically calculated electronic circular dichroism methods for (+)-8 and (-)-9. Compounds 3, 5, (-)-8, (+)-8, (+)-9, and (-)-9 displayed cytotoxic activity toward several human tumor cell lines, with (-)-8 and (-)-9 being the most potent.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Natural Products
volume
75
issue
5
pages
859 - 864
publisher
The American Chemical Society
external identifiers
  • wos:000304385800002
  • scopus:84861548743
ISSN
0163-3864
DOI
10.1021/np200645p
language
English
LU publication?
yes
id
dbd92896-c571-4de5-af2f-94055056ffe0 (old id 2809502)
date added to LUP
2012-06-25 16:46:30
date last changed
2017-01-01 05:29:23
@article{dbd92896-c571-4de5-af2f-94055056ffe0,
  abstract     = {The enantiomeric lactams (-)-8, (+)-8, (+)-9, and (-)-9 were formed by the reaction of the dimeric phthalide rac-tokinolide B (rac-3) with (R)-(+)-alpha-methylbenzylamine and (S)-(-)-alpha-methylbenzylamine. The absolute configurations of compounds 8 and 9 were assigned by experimental and theoretically calculated electronic circular dichroism methods for (+)-8 and (-)-9. Compounds 3, 5, (-)-8, (+)-8, (+)-9, and (-)-9 displayed cytotoxic activity toward several human tumor cell lines, with (-)-8 and (-)-9 being the most potent.},
  author       = {Leon, Alejandra and Antonio Cogordan, J. and Sterner, Olov and Delgado, Guillermo},
  issn         = {0163-3864},
  language     = {eng},
  number       = {5},
  pages        = {859--864},
  publisher    = {The American Chemical Society},
  series       = {Journal of Natural Products},
  title        = {Enantiomeric Derivatives of Tokinolide B: Absolute Configuration and Biological Properties},
  url          = {http://dx.doi.org/10.1021/np200645p},
  volume       = {75},
  year         = {2012},
}