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

In English

Författare

  • Ulf Berg
  • Håkan Bladh
  • Konstantin Mpampos

Summary, in English

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.

Publiceringsår

2004

Språk

Engelska

Sidor

2125-2130

Publikation/Tidskrift/Serie

Organic and Biomolecular Chemistry

Volym

2

Issue

14

Dokumenttyp

Artikel i tidskrift

Förlag

Royal Society of Chemistry

Ämne

  • Organic Chemistry

Status

Published

ISBN/ISSN/Övrigt

  • ISSN: 1477-0539