Spirobicyclo[2.2.2]octane derivatives: mimetics of baccatin III and paclitaxel (Taxol).
The formylated spirobyclic alcohol was computer modeled to be a mimetic of paclitaxel. In this model, the formyl group was used as a truncated paclitaxel side chain in order to reduce the computational work. Compound , carrying the paclitaxel side chain, was synthesized in six steps from optically active 1,3-diketone . Microtubule stabilization was not observed for , indicating that the model needs to be adjusted.
Almqvist
Fredrik
F
Department of Organic Chemistry, Umeå University, Umeå, Sweden.
Manner
Sophie
S
Thornqvist
Viveca
V
Berg
Ulf
U
Wallin
Margareta
M
Frejd
Torbjorn
T
D000470:Alkaloids / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry*; D040761:Biomimetic Materials / Q000737:chemistry*; D003198:Computer Simulation; D008958:Models, Molecular; D009795:Octanes / Q000737:chemistry*; D017239:Paclitaxel / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*; D043823:Taxoids / Q000737:chemistry*
D000470:Alkaloids; D000970:Antineoplastic Agents; D009795:Octanes; D013141:Spiro Compounds; D043823:Taxoids; C509760:spirobicyclo(2.2.2)octane; C073950:baccatin III; D017239:Paclitaxel