Aromatic Guanidine Alkaloids

The bioluminescence of crustaceans belonging to genera Cypridina is due to the reaction of Cypridina luciferin (23) with luciferase in the presence of oxygen [41,42], 

The structure of Cypridina luciferin was established by analysis of spectroscopic data, chemical degradations, extensive MS analysis, and total synthesis [41—44]. Cypridina luciferin is biosynthesized from L-tryptophan, L-arginine, and L-isoleudne [45,46]. Distomadines A (24) and B (25) have been isolated from the asddian Pseudodistoma aureum and were not adive in antifungal, antiviral, anti-inflammatory, and anti-mycobacterial bioassays [47]. 

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Figure 22. Selected structures of aromatic guanidine alkaloids.

A double tethered Biginelli reaction was carried out on the simple five-membered urea aldehyde 305 that reacted with the aliphatic and aromatic bis-ketoesters 306 and 307 giving compounds 308 and 309, respectively, in good yield, albeit with a diasteromeric ratio of 1 3. A series of different polycyclic bis-guanidines resembling betzelladine alkaloids were prepared <2003OL4485>. 

Didemnum Phenylethylamlne derivatives pyridoacridines alkaloids of pyrrole (lamellarins), Indole (eudistomins), carbazole and guanidine aromatic and heteroaromatic S/N derivatives (thiazole-rich cyclic peptides) halogenated nucleosides... 

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