Eleutherobin

Title: Eleutherobin
CAS Registry Number: 174545-76-7
CAS Name: [(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-b-D-arabinopyranoside 2-acetate
Molecular Formula: C35H48N2O10
Molecular Weight: 656.76
Percent Composition: C 64.01%, H 7.37%, N 4.27%, O 24.36%
Literature 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).
Properties: White non-crystalline solid. [a]D25 -49.3°. (c = 3 in methanol). uv max (methanol): 290 nm (log e 3.824).
Optical Rotation: [a]D25 -49.3°. (c = 3 in methanol)
Absorption maximum: uv max (methanol): 290 nm (log e 3.824)
Use: Biological reagent for tubulin and microtubulin studies.
Elgodipine Ellagic Acid Ellipticine Elliptinium Acetate Elliptone

Eleutherobin
Eleutherobin.png
Identifiers
PubChem 6918335
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Eleutherobin is a marine diterpene glycoside with anticancer activity.