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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
; ; and
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 (ACS)
external identifiers
  • wos:000304385800002
  • scopus:84861548743
  • pmid:22574648
ISSN
0163-3864
DOI
10.1021/np200645p
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
dbd92896-c571-4de5-af2f-94055056ffe0 (old id 2809502)
date added to LUP
2016-04-01 13:08:18
date last changed
2022-02-19 03:12:46
@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 (ACS)}},
  series       = {{Journal of Natural Products}},
  title        = {{Enantiomeric Derivatives of Tokinolide B: Absolute Configuration and Biological Properties}},
  url          = {{http://dx.doi.org/10.1021/np200645p}},
  doi          = {{10.1021/np200645p}},
  volume       = {{75}},
  year         = {{2012}},
}