8298. Rutecarpine

Nomenclature

CAS number: 84-26-4
8,13-Dihydroindolo[2′,3′:3,4]pyrido[2,1-b]quinazolin-5(7H)-one; rutaecarpine.
C18H13N3O; mol wt 287.32.
C 75.24%, H 4.56%, N 14.62%, O 5.57%.

Description and references

From fruit of Evodia rutaecarpa Hook. & Thoms. and Hortia arborea Engl., Rutaceae: Asahina, Kashiwaki, J. Pharm. Soc. Jpn. 1915, 1293; Pachter et al., J. Am. Chem. Soc. 82, 5187 (1960). Structure: Y. Asahina, J. Pharm. Soc. Jpn. 1924, 1. Synthesis: Y. Asahina et al., J. Chem. Soc. 1927, 1708; T. Kametani et al., J. Am. Chem. Soc. 99, 2306 (1977); eidem, Chem. Pharm. Bull. 26, 1922 (1978); H. M"ohrle et al., Arch. Pharm. 313, 990 (1980); J. Bergman, S. Bergman, Heterocycles 16, 347 (1981). Simple synthesis: J. K"ok"osi et al., Tetrahedron Lett. 22, 4861 (1981). Synthesis under physiological conditions: Sch"opf, Angew. Chem. 50, 779, 797 (1937). Biosynthesis: M. Yamazaki et al., Tetrahedron Lett. 1966, 3221; 1967, 3317. Mass spec.: J. Tamas et al., Acta Chim. Acad. Sci. Hung. 89, 85 (1976).

Chemical structure

Properties

Needles from ethyl acetate, mp 259.5-260°. uv max (ethanol): 278, 290, 332, 345, 364 nm (log ε 3.83, 3.88, 4.49, 4.54, 4.44). Sol in alc, benzene, chloroform, ether. Practically insol in water.