C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 493/22 (2006.01) A61K 31/35 (2006.01) A61K 31/357 (2006.01) A61P 35/00 (2006.01)
Patent
CA 2464687
A series of novel antimitotic macrolides based on the structure of Spirastrellolide A, which was isolated from the Caribbean marine sponge Spirastrella occinea, are described. Spirastrellolide A has a 47 carbon linear polyketide backbone incorporated into a highly functionalized 38 membered lactone containing a tetrahydropyran and two spiro bispyran substructures embedded in the macrocycle and a side chain terminating in a carboxylic acid. Spirastrellolide A's structure was elucidated by detailed spectroscopic analysis of its methyl ester. Spirastrellolide A methyl ester shows potent activity in a cell-based assay that detects mitotic arrest, but it does not affect tubulin polymerization in vitro. It has the unusual biological property of being able to accelerate entry of cells into mitosis from other cell-cycle stages, before it arrests them in mitosis.
Andersen Raymond
Roberge Michel
Williams David
Andersen Raymond
Roberge Michel
The University Of British Columbia
Williams David
LandOfFree
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