Antitumorigenic lactone derivative

Details Antitumorigenic lactone derivative Antitumorigenic lactone derivative

1978-02-03

1980-07-29

Trousof, Natalie

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424279, C07D30793

Patent

active

042150493

ABSTRACT:
There are disclosed novel compounds which are extracted with an organic solvent from Eupatorium sachalinense belonging to the genus Eupatorium and isolated by normal separating and refining procedures, the compounds being expressed by the general formula: ##STR1## where R is ##STR2## a pale yellowish oily substance having an optical rotation of [.alpha]sub.D.sup.24 -121.degree. (C=O.75, ethanol), a molecular weight of 420 estimated from peak value in mass spectrum measurement (theoretical value: 420), a molecular formula of C.sub.22 H.sub.28 O.sub.8, an end absorption at 210 mm (.epsilon.:14800) in ultraviolet absorption spectrum, peaks in infrared absorption spectrum by liquid film method at the frequencies (cm.sup.-1) of 3400, 2920, 2845, 1760, 1740, 1705, 1658, 1440, 1370, 1325, 1220-1280, 1180, 1133, 1107, 1070, 1020, 970, 881, 840, 819, 788, 758, 710, 662, 630, 607 and 582, assignments of respective protons in NMR spectrum (.delta.,CDCl.sub.3) at C.sub.6 --H=5.96 (1H, dd, J=11,2), C.sub.4 --CH.sub.3 =1.80 (3H, d, J=1), C.sub.10 --CH.sub.3 =1.84 (3H, s), C.sub.3' --H=6.90 (1H, t, J=5.5), C.sub.4' --H=4.37 (2H, d, J=5.5), C.sub.5' --H=4.31 (2H, s), exo CH.sub.2 =5.79,6.33 (1H, d, J=2), COCH.sub.3 = 2.12 (3H, s); ##STR3## or [III] hydrogen; and a process for the preparation of these compounds. These compounds are found to have not only inhibitive effects, even in a low concentration, against experimental cancer cells (HeLa) but also considerable life prolonging effects in in vitro experiments on mice inoculated with Ehrlich ascites, suggesting similar effects on malignant tumors in humans.

REFERENCES:
Dolejs et al., Chem. Abstracts, vol. 58, 10244.
Chem. Abstracts, 1967-1971, Subject Index.
Kupchan et al., J. Org. Chem., vol. 38, No. 12, 1973, p. 2189 and vol. 38, pp. 2189-2196.
Holub et al., Collection Czchoslov. Chem. Commun., 42, 1053-1064, 1976.
Drozdz, Collection Czchoslov Chem. Commun., 37, 1546, 1972.

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