Stereochemical variations on the colchicine motif. Peracid oxidation of thiocolchicone. Synthesis, conformation and inhibition of microtubule assembly
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/139447
- author
- Berg, Ulf LU ; Bladh, Håkan and Mpampos, Konstantin LU
- organization
- publishing date
- 2004
- 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
- pmid:15254641
- ISSN
- 1477-0539
- DOI
- 10.1039/b402840f
- 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
- 1e3e8517-316c-47fb-8c15-58084740f5dd (old id 139447)
- date added to LUP
- 2016-04-01 12:36:00
- date last changed
- 2022-01-27 07:17:23
@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}}, doi = {{10.1039/b402840f}}, volume = {{2}}, year = {{2004}}, }