1016. Bebeerine
Nomenclature
CAS number: 477-60-1
(13aS,25aS)-2,3,13a,14,15,16,25,25a-Octahydro-18,29-dimethoxy-1,14-dimethyl-13H-4,6:21,24-dietheno-8,12-metheno-1H-pyrido[3′,2′:14,15][1,11]dioxacycloeicosino[2,3,4-ij]isoquinoline-9,19-diol; 1′α-6,6′-dimethoxy-2,2′-dimethyltubocuraran-7′,12′-diol; d-bebeerine; chondodendrine; pelosine. C36H38N2O6; mol wt 594.70.
C 72.71%, H 6.44%, N 4.71%, O 16.14%.
Description and references
From bark of Nectandra rodioei Hook., Lauraceae: Maclagan, Ann. 48, 106 (1843). From root of Chondodendron microphyllum (Eichl.) Moldenke and stem of Ch. candicans (Rick ex. D.C.) Sandwith, Menispermaceae and radix pareirae bravae: King, J. Chem. Soc. 1940, 737. Structure: Faltis et al., Ber. 69, 1269 (1936); King, J. Chem. Soc. 1939, 1157. Stereochemistry: King, ibid. 1948, 265.
Properties
Needles from methanol, mp 215°. [α]D20 +345.7° (c = 0.4 in 1N HCl). Sol in benzene, chloroform, pyridine.Derivative
Hydrochloride.C36H38N2O6.HCl; mol wt 631.16.
C 68.51%, H 6.23%, N 4.44%, O 15.21%, Cl 5.62%.
Properties
mp 260°. [α]D20 +294° (c = 0.7). Sol in water and alcohol.Therapeutic Category
Antimalarial.
Keywords
Antimalarial