hymenidin and oroidin

We have prepared three alkaloids from the Agelas sponges, clathrodin, hymenidin and oroidin, and a series of their synthetic analogues, and evaluated their inhibitory effect against six isoforms of the K

Topics: Dose-Response Relationship, Drug; Humans; Molecular Structure; Potassium Channel Blockers; Potassium Channels, Voltage-Gated; Pyrroles; Structure-Activity Relationship

The total syntheses of oroidin, hymenidin and clathrodin are reported via the intermediacy of an imidazo[1,2-a]pyrimidine derivative. The chemistry described herein obviates the need for expensive guanidine reagents, multiply protected prefunctionalized 2-aminoimidazole synthons, or the need for laborious olefinations thereby achieving synthetic efficiency amenable to scale-up. The approach outlined in this manuscript provides an opportunity for further functionalizations through the imidazo[1,2-a]pyrimidine core and through functional groups placed strategically on the side chain.

Topics: Models, Molecular; Pyrimidines; Pyrroles

A detailed analysis of the secondary metabolites of a specimen of Agelas sventres was carried out here for the first time. The chemistry of Agelas sponges is dominated by bromopyrrole derivatives. Besides three known bromopyrrole metabolites, a new compound, sventrin (1), was isolated and its structure identified using spectroscopic methods. Sventrin (1) was shown to be a feeding deterrent compound against a common omnivorous reef fish.

Topics: Alkaloids; Animals; Bahamas; Carboxylic Acids; Chromatography, High Pressure Liquid; Feeding Behavior; Fishes; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Porifera; Pyrroles; Spectrophotometry, Ultraviolet; Spectroscopy, Fourier Transform Infrared