1-Methoxy-9H-carbazole-3-carbaldehyde

Description

This simple carbazole alkaloid is found in the stem bark of Mu"aya koenigii Spreng. It is best purified by sublimation of the crude base when it yields colour_x0002_less crystals. The ultraviolet spectrum in ethanol has absorption maxima at 238, 247,274,289 and 335 mJJ.. The structure has been shown to be 3-formyl-lmethoxycarbazole by spectroscopic methods and synthesis. It yields an oxime, m.p. l55-6°C; a picrate, m.p. 198-2000 C and the 2:4-dinitrophenylhydrazone, m.p. > 300°C. The N-methyl derivative forms colourless needles from C6H6- light petroleum, m.p. l48-9°C. When subjected to Wolff-Kishner reduction, the alkaline phase yields l-hydroxy-3-methyl-carbazole.

Uses

Murrayanine is a carbazole alkaloid. Murrayanine suppresses the proliferation and metastasis of human breast cancer cells via induction of apoptosis and inhibition of RANK/RANKL signaling pathway.

Definition

ChEBI: A natural product found in Clausena harmandiana.

References

Chakraborty, Barman, Bose., Tetrahedron, 21, 681 (1965)
Synthesis: Crum, Sprague., Chern. Cornrnun., 417 (1966)
Chakraborty, Chowdhury., J. Org. Chern., 33, 1265 (1968)

Raw materials

Preparation Products