3-Alkylpyridine from marine sponges

Monomers of 3-alkylpyridines from marine sponges (eontinuation)... 

AKYLPYRIDINIUM AND 3-ALKYLPYRIDINE COMPOUNDS FROM MARINE SPONGES, THEIR SYNTHESIS, BIOLOGICAL ACTIVITIES AND POTENTIAL USE... 

Table I. Cytotoxic activity of 3-alkylpyridine and 3-alkylpyridinium compounds from marine sponges on...

The monomeric structural unit of the 3-alkylpiperidine alkaloids is readily apparent in a number of simple 3-alkylpyridines isolated from marine sponges. In all known examples, the 3-alkyl component of the monomeric unit is attached to a primary amine, methyl amine, methoxy amine, methoxy methyl amine, imine oxide or oxime methyl ether functionality at the distal terminus. 

Andersen, R.J., Van Soest, R.W.M., and Kong, F. (1996) 3-Alkylpyridine alkaloids isolated from marine sponges in the order Haplosclerida, in Alkaloids Chemical and Biological Perspectives, vol. 10 (ed. S.W. Pelletier), Pergamon Press, Amsterdam, Boston, London, pp. 301-355. 

Arai, M Ishida, A., Setiawan, A., and Kobayashi, M. (2009) Haliclonacydamines, tetracyclic alkylpyridine alkaloids, as anti-dormant mycobacterial substances from a marine sponge of Haliclona sp. Chem. Pharm. Butt., 57,1136-1138. 

Tsukamoto, S., Takahashi, M., Matsunaga, S., Fusetani, N., and Van Soest, RW.M. (2000) Hachijodines A-G seven new cytotoxic 3-alkylpyridine alkaloids from two marine sponges of the genera Xestospongia and Amphimedon. J. Nat. Prod., 63, 682-684. 

Alkylpyridines are rare in the marine environment and the only similar derivatives currently known are 3-aIkyl-pyridines isolated from certain haplosderid sponges (see Chapter 19). 

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