Title: Tylocrebrine
CAS Registry Number: 6879-02-3
CAS Name: 9,11,12,13,13a,14-Hexahydro-2,3,5,6-tetramethoxydibenzo[f,h]pyrrolo[1,2-b]isoquinoline
Additional Names: 2,3,5,6-tetramethoxyphenanthro[9,10:6¢,7¢]indolizidine
Molecular Formula: C24H27NO4
Molecular Weight: 393.48
Percent Composition: C 73.26%, H 6.92%, N 3.56%, O 16.26%
Literature References: Phenanthroindolizidine alkaloid; isomeric with tylophorine, q.v. Isoln of l-isomer from Tylophora crebriflora S. T. Blake, Asclepiadaceae: E. Gellert et al., J. Chem. Soc. 1962, 1008; K. V. Rao et al., J. Pharm. Sci. 59, 1501 (1970). Antileukemic activity: E. Gellert, R. Rudzats, J. Med. Chem. 7, 361 (1964). d-Isomer isolated from Ficus septica, Moraceae. Synthesis of the dl-form and structure: E. Gellert et al., loc. cit.; B. Chauncy, E. Gellert, Aust. J. Chem. 23, 2503 (1970). Inhibits protein synthesis: G. R. Donaldson et al., Biochem. Biophys. Res. Commun. 31, 104 (1968); E. Battaner, D. Vasquez, Biochim. Biophys. Acta 254, 316 (1971). Mode of action studies: M. T. Huang, A. P. Grollman, Mol. Pharmacol. 8, 538 (1972). Review: R. S. Gupta, Antibiotics 6, 47 (1983).
Derivative Type: dl-Form
Properties: Needles from chloroform + methanol, mp 219-221°.
Melting point: mp 219-221°
Derivative Type: l-Form
Properties: Crystals from methanol, dec 218-220°. uv max: 263, 342, 360 nm (log e 4.81, 3.25, 3.09). [a]D24 -45° (c = 0.74 in chloroform). pKa (50% aq ethanol): 6.7.
pKa: pKa (50% aq ethanol): 6.7
Optical Rotation: [a]D24 -45° (c = 0.74 in chloroform)
Absorption maximum: uv max: 263, 342, 360 nm (log e 4.81, 3.25, 3.09)
Derivative Type: d-Form
Properties: Crystals from methanol, mp 220-222°. [a]D22 +20.5°.
Melting point: mp 220-222°
Optical Rotation: [a]D22 +20.5°
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