3545. Eleutherobin
Nomenclature
CAS number: 174545-76-7
[(4R,4aS,5Z,7R,10S,11S,12aR)-3,4,4a,7,10,11,12,12a-Octahydro-7-methoxy-1,10-dimethyl-4-(1-methylethyl)-11-[[(2E)-3-(1-methyl-1H-imidazol-4-yl)-1-oxo-2-propenyl]oxy]-7,10-epoxybenzocyclodecen-6-yl]methyl-β-d-arabinopyranoside 2-acetate. C35H48N2O10; mol wt 656.76.
C 64.01%, H 7.37%, N 4.27%, O 24.36%.
Description and references
Cytotoxic glycosylated diterpene isolated from the marine soft coral, Eleutherobia sp. Enhances tubulin polymerization and stablization of microtubules similar to paclitaxel, q.v. Isoln and structure determn: W. H. Fenical et al., US 5473057 (1995 to Univ. Calif.). Induction of tubulin polymerization and mode of action: B. H. Long et al., Cancer Res. 58, 1111 (1998). Total synthesis: K. C. Nicolaou et al., J. Am. Chem. Soc. 120, 8674 (1998); X. T. Chen et al., ibid. 121, 6563 (1999). Solid-state and solution conformations: B. Cinel et al., Tetrahedron Lett. 41, 2811 (2000). Structure-activity: I. Ojima et al., Proc. Natl. Acad. Sci. USA 96, 4256 (1999). Brief review: T. Lindel, Angew. Chem. Int. Ed. 37, 774-776 (1998).
