9254. Thalicarpine

Nomenclature

CAS number: 5373-42-2
(6aS)-9-[4,5-Dimethoxy-2-[[(1S)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]phenoxy]-5,6,6a,7-tetrahydro-1,2,10-trimethoxy-6-methyl-4H-dibenzo[de,g]quinoline.
C41H48N2O8; mol wt 696.83.
C 70.67%, H 6.94%, N 4.02%, O 18.37%.

Description and references

Tumor-inhibitory alkaloid from Thalictrum dasycarpum Fisch. & Lall., Ranunculaceae: Kupchan et al., J. Pharm. Sci. 52, 985 (1963). Structure: Kupchan, Yokoyama, J. Am. Chem. Soc. 86, 2177 (1964); Tomita et al., Tetrahedron Lett. 1965, 4309. Total synthesis: Kupchan, Liepa, Chem. Commun. 1971, 599; Kupchan et al., J. Am. Chem. Soc. 95, 2995 (1973). Pharmacology: Herman, Chadwick, Toxicol. Appl. Pharmacol. 26, 137 (1973); S. M. Sieber et al., Cancer Treat. Rep. 60, 1127 (1976). Antimicrobial and hypotensive activity: W. N. Wu et al., Lloydia 40, 508 (1977). Biosynthesis: D. S. Bhakuni, S. Jain, Tetrahedron 38, 729 (1982).

Chemical structure

Properties

Needles from ethyl acetate, mp 160-161°. [α]D25 +133° (c = 0.83 in methanol); [α]D25 +89° (c = 0.88 in chloroform). uv max (methanol): 282, 302 nm (ε 17,000, 13,000).