Pseudoceratidine

The related pseudoceratidine (140) inhibits Balanus amphitrite with an EC50 of 15 pg/ml [110]. 

The antifouling sponge metabolite pseudoceratidine (1245) was characterized from the Japanese Pseudoceratina purpurea (1253). This spermidine derivative has excellent larval settlement and metamorphosis inhibitory activity against the barnacle Balanus amphitrite (ED50 = 8.0 pig cm-3), and is the first example of an antifouling spermidine derivative. The four tauroacidins A (1246/1247) and B (1248/1249), with tyrosine kinase inhibitory activity, were isolated from the... 

Tsukamoto S, Kato H, Hirota H, Fusetani N (1996) Pseudoceratidine A New Antifouling Spermidine Derivative from the Marine Sponge Pseudoceratina purpurea. Tetrahedron Lett 37 1439... 

Ponasik, J.A., Kassab, D.J., and Ganem, B., Synthesis of the antifouling polyamine pseudoceratidine and its analogs factors influencing biocidal activity, Tetrahedron Lett., 37, 6041, 1996. 

Tsukamoto, S., Kato, H., Hirota, H., and Fusetani, N., Pseudoceratidine a new antifouling spermidine derivative from the marine sponge Pseudoceratina purpurea, Tetrahedron Lett., 37, 1439, 1996. 

Two syntheses of pseudoceratidine (120), which was reported to inhibit metamorphosis of the barnacle Balanus amphitrite, have been described [146,147]. To delineate the structural requirements for this bioactivity, the corresponding N-1 and N-8 mono-(4,5-dibromo-2-pyrrolyl) amides of spermidine were also synthesized, as well as the closely related mono- and bis-(4,5-dibromo-2-pyrrolecarboxamido) residues to test the importance of the pyrrole substituents and the positively charged secondary amine group in 120 [148]. 

Behrens, C., Christoflfersen, M.W, Gram, L., and Nielsen, P.H. (1997) A convenient synthesis of pseudoceratidine and three analogs for biological evaluation. Bioorg. Med. Chem. Lett., 7, 321-326. 

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