Cytotoxic tris(oxazole)-containing macrolides

Details Cytotoxic tris(oxazole)-containing macrolides Cytotoxic tris(oxazole)-containing macrolides

2001-01-12

2002-05-21

Berch, Mark L (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C540S469000

Reexamination Certificate

active

06391900

ABSTRACT:

The present invention relates to new cytotoxic tris(oxazole)-containing macrolides obtained by chemical modification of marine natural products.
BACKGROUND OF THE INVENTION
Marine organisms, especially soft corals, sponges and tunicates, provide many secondary metabolites and exhibit a varying degree of biological activity (Reference 1). An important family of these metabolites is the cytotoxic tris(oxazole)-containing macrolide family; in 1986 it was reported the structure of the three first tris(oxazole)-containing macrolides: Ulapualide A and B (Reference 2) and Kabiramide C (Reference 3).
Since then, over 30 additional tris(oxazole)containing macrolides have been published (Reference 4).
SUMMARY OF THE INVENTION
The present invention relates to now cytotoxic tris(oxazole)-containing macrolides having the formula (I):
wherein X represents a lower alkyl; R
1
and R
2
represent hydrogen or lower alkyl; R
3a
represents hydrogen, and R
3b
represents
or R
3a
and R
3b
together represent oxygen; R
4
represents hydrogen, lower alkoxy or lower alkyl; R
5
represents hydrogen, carbarnoyl, or lower alkanoyl; R
6a
represents hydrogen, and R
6b
represents hydroxy, or R
6a
and R
6b
together represent oxygen; R
7
represents hydrogen, lower alkyl, or hydroxymethyl; R
8
represents lower alkoxy or lower alkyl; Y
1
represents hydrogen or methyl, and y
2
represents hydrogen, or Y
1
and Y
2
together represent a double bond.


REFERENCES:
patent: 5760065 (1998-06-01), Nonomura et al.
patent: 0 729 950 (1995-09-01), None
Faulkner, D.Nat. Prod. Rep.1997, 14, 259-302.
Scheuer, P.J. et al.,J. Am. Chem. Soc.1986, 108, 846-847.
Fusetani, N. et al.,J. Am. Chem. Soc., 1986, 108, 847-849.
Marine Biotechnology, Vol. 1, Ed. By David H. Attaway and Oskar R. Zaborsky, Plenum Press, New York 1993, pp. 211-213.
Raymond J. Bergeron et al., “Antineoplastic and Antiherpetic Activity of Spermidine Catecholamide Iron Chelators”,Biochem. Bioph. Res. Comm. 1984, 121, 848-854.
Fusetani, N. et al.,J. Org. Chem., 1989, 54, 1360-1364.

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