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Stereochemical variations on the colchicine motif. Peracid oxidation of thiocolchicone. Synthesis, conformation and inhibition of microtubule assembly

Berg, Ulf LU ; Bladh, Håkan and Mpampos, Konstantin LU (2004) In Organic and Biomolecular Chemistry 2(14). p.2125-2130
Abstract
When 7-oxodesacetamidothiocolchicine ( 1) was treated with various peroxides in order to afford a Baeyer-Villiger rearrangement, a complex mixture of products was formed, which included the sulfoxide, ( 2) and sulfone, ( 3). When peracetic acid was used two additional products were formed; a C-ring lactone ( 4) and a ring-contracted allocolchicine derivative ( 5). The sulfoxide ( 2) was semi-preparatively resolved into enantiomers by chromatography on microcrystalline triacetylcellulose. Rotational barriers around the A - C pivot bond of 2, 4 and 5 were determined by dynamic H-1 NMR analysis. The compounds 2, 3, 4 and 7a exhibit moderate inhibition of tubulin polymerization, according to in vitro turbidity studies, whereas 5 was inactive.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Organic and Biomolecular Chemistry
volume
2
issue
14
pages
2125 - 2130
publisher
Royal Society of Chemistry
external identifiers
  • pmid:15254641
  • wos:000222639100026
  • scopus:3843103610
ISSN
1477-0539
DOI
10.1039/b402840f
language
English
LU publication?
yes
id
1e3e8517-316c-47fb-8c15-58084740f5dd (old id 139447)
date added to LUP
2007-07-10 09:05:20
date last changed
2017-01-01 05:17:16
@article{1e3e8517-316c-47fb-8c15-58084740f5dd,
  abstract     = {When 7-oxodesacetamidothiocolchicine ( 1) was treated with various peroxides in order to afford a Baeyer-Villiger rearrangement, a complex mixture of products was formed, which included the sulfoxide, ( 2) and sulfone, ( 3). When peracetic acid was used two additional products were formed; a C-ring lactone ( 4) and a ring-contracted allocolchicine derivative ( 5). The sulfoxide ( 2) was semi-preparatively resolved into enantiomers by chromatography on microcrystalline triacetylcellulose. Rotational barriers around the A - C pivot bond of 2, 4 and 5 were determined by dynamic H-1 NMR analysis. The compounds 2, 3, 4 and 7a exhibit moderate inhibition of tubulin polymerization, according to in vitro turbidity studies, whereas 5 was inactive.},
  author       = {Berg, Ulf and Bladh, Håkan and Mpampos, Konstantin},
  issn         = {1477-0539},
  language     = {eng},
  number       = {14},
  pages        = {2125--2130},
  publisher    = {Royal Society of Chemistry},
  series       = {Organic and Biomolecular Chemistry},
  title        = {Stereochemical variations on the colchicine motif. Peracid oxidation of thiocolchicone. Synthesis, conformation and inhibition of microtubule assembly},
  url          = {http://dx.doi.org/10.1039/b402840f},
  volume       = {2},
  year         = {2004},
}