3548. Ellipticine

Nomenclature

CAS number: 519-23-3
5,11-Dimethyl-6H-pyrido[4,3-b]carbazole.
C17H14N2; mol wt 246.31.
C 82.90%, H 5.73%, N 11.37%.

Description and references

Antitumor alkaloid isolated from Ochrosia elliptica Labill., O. sandwicensis A. DC., O. viellardii, O. silvatica, Apocynaceae: Goodwin et al., J. Am. Chem. Soc. 81, 1903 (1959); Kan Fan et al., Phytochemistry 9, 1351 (1970); Cosson, Schmid, ibid. 1353. Structure and synthesis: Woodward et al., J. Am. Chem. Soc. 81, 4434 (1959). Syntheses: J. Bergman, R. Carlsson, Tetrahedron Lett. 1977, 4663; D. A. Taylor et al., J. Chem. Res. Miniprint 1979, 4801; S. Kano et al., J. Org. Chem. 46, 2979 (1981); R. Besselievre, H. P. Husson, Tetrahedron 37, 241 (1981). Regioselective synthesis: T.-L. Ho, S.-Y. Hsieh, Helv. Chim. Acta 89, 111 (2006). Toxicity study: Rakieten et al., U.S. Gov. Res. Dev. Rep. 67, 38 (1967), C.A. 68, 20827g (1968). Review of syntheses: M. Sainsbury, Synthesis 1977, 437-448; R. Barone, M. Chanon, Heterocycles 16, 1357-1365 (1981). Review of antineoplastic activity: K. W. Kohn et al., Antibiotics vol. 5 (pt. 2), F. E. Hahn, Ed. (Springer-Verlag, New York, 1979) pp 195-213.

Chemical structure

Properties

Bright yellow needles from ethyl acetate, mp 311-315° (dec). uv max: 239, 277, 286, 294, 332, 382, 400 nm (log ε 4.23, 4.61, 4.76, 4.74, 3.65, 3.61, 3.53). LD50 in mice (mg/kg): 19.5-22.4 i.v.; 178-204 orally (Rakieten).