Structures, semisyntheses, and absolute configurations of the antiplasmodial α-substituted ß-lactam monamphilectines B and C from the sponge Svenzea flava.
Tetrahedron
; 71(3): 487-494, 2015 Jan 21.
Article
em En
| MEDLINE
| ID: mdl-26494928
ABSTRACT
Bioassay-guided fractionation of the Caribbean sponge Svenzea flava collected near Mona Island, off the west coast of Puerto Rico, led to the isolation of two isocyanide amphilectane-type diterpenes named monamphilectines B and C (2 and 3). Attached to the backbone of each of these compounds is the first α-substituted monocyclic ß-lactam ring to be isolated from a marine organism. The molecular structures of 2 and 3 were established by spectroscopic methods and then confirmed unequivocally by chemical correlation and comparison of physical and chemical data with the natural products. The new ß-lactams were successfully synthesized in one step, starting from the known diisocyanide 4, via parallel Ugi four-center three-component reactions (U-4C-3CR) that also established their absolute stereostructures. Interestingly, compounds 2 and 3 exhibited activities in the low nanomolar range against the human malaria parasite Plasmodium falciparum.
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MEDLINE
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En
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Tetrahedron
Ano de publicação:
2015
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Article