6834. Olivacine

Nomenclature

CAS number: 484-49-1
1,5-Dimethyl-6H-pyrido[4,3-b]carbazole; guatambuinine.
C17H14N2; mol wt 246.31.
C 82.90%, H 5.73%, N 11.37%.

Description and references

Isolated from the bark and stem of Aspidosperma olivaceum Müll. Arg., A. australe Müll. Arg., A. longepetiolatum Kuhlm., Apocynaceae: Schmutz, Hunziger, Pharm. Acta Helv. 33, 341 (1958). Identity with guatambuinine: Marini-Bettolo, Carvalho-Ferreira, Ann. Chim. 49, 869 (1959). Structure: Marini-Bettolo, Schmutz, Helv. Chim. Acta 42, 2146 (1959); Ondetti, Deulofeu, Tetrahedron 15, 160 (1961). Synthesis: Schmutz, Wittwer, Helv. Chim. Acta 43, 793 (1960); Wenkert, Dave, J. Am. Chem. Soc. 84, 94 (1962); Mosher et al., J. Med. Chem. 9, 237 (1966); R. Besselievre, H. Husson, Tetrahedron Lett. 1976, 1873; J. Bergman, R. Carlsson, ibid. 1978, 4055; J. P. Kutney et al., Heterocycles 16, 1469 (1981).

Chemical structure

Properties

Fine yellow needles from dilute methanol, yellow prisms from undiluted methanol, mp 317-325°. Fluoresces in dilute alcoholic soln. uv max (ethanol): 224, 238, 276, 287, 292, 314, 329, 375 nm (log ε 4.39, 4.33, 4.70, 4.85, 4.83, 3.66, 3.80, 3.66). Soly in methanol, acetone, chloroform, carbon tetrachloride, carbon disulfide, tetrahydrofuran, dioxane less than 1%.