Crambescidins: new antiviral and cytotoxic compounds from the sp

Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system

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514258, C07D49122, A61K 31505

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active

057567344

ABSTRACT:
The present invention is directed to several novel compounds isolated from the sponge Crambe crambe, and designated herein as Crambescidin 816 (Compound 1), Crambescidin 830 (Compound 2), Crambescidin 844 (Compound 3), and Crambescidin 800 (Compound 4), as well as several derivatives thereof. The 816, 830, 844 and 800 compounds are four preferred species of complex pentacyclic guanidines linked by a linear .omega.-hydroxy fatty acid to a hydroxyspermidine, that have been obtained by a bioassay-guided isolation procedure, involving solvent partition and chromatography on Sephadex LH-20, cyano, and C-18 columns, from extracts of the red, encrusting sponge Crambe crambe (Order Poecilosclerida, Family Esperiopsidae).

REFERENCES:
Jares-Erijman et al, J. Org. Chem. 56, pp. 5712-5715 (Sep. 13, 1991).
Schmitz et al., Journal of Natural Products, vol. 54, No. 6 pp. 1469-1490 (1991).
Kashman et al, J. Amer. Chem. Soc., 111: 8925-8926 (1989).
Rosano et al., J. Backeriol., 135: 805-808 (1978).
Harbour et al., J. Amer. Chem. Soc., 103: 5604-5606 (1981).
Berlinck et al., Tetrahedron Letters, 31: 6531-6534 (1990).

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