PubMed · 14851787
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V VISKOTOVA. 1951-06-15. [Menotoxin].. https://pubmed.ncbi.nlm.nih.gov/14851787/
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Bulbs and leaves of Boophane disticha are used in South African traditional medicine in the treatment of anxiety. Crude extracts of the leaves have shown affinity to the SSRI site on the serotonin transporter in a radioligand binding assay. In this study, two compounds, buphanadrine and buphanamine, were isolated by bioassay-guided fractionation on VLC and preparative TLC. The structures of the compounds were determined by (1)H and (13)C NMR. Fractions were tested for affinity to the serotonin transporter in a binding assay using [(3)H]-citalopram as ligand. The IC(50) values of buphanidrine and buphanamine were 274 microM (K(i)=132 microM) and 1799 microM (K(i)=868 microM), respectively. The two alkaloids were also tested for affinity to the 5HT(1A) receptor, but only showed slight affinity.
A unified strategy for the synthesis of mauritines A (5), B (6), C (7), and F (10) has been developed based on a key intramolecular nucleophilic aromatic substitution reaction (S(N)Ar) for the formation of the strained 14-membered paracyclophane. It was demonstrated that the outcome of the cycloetherification is independent of the stereochemistry of the peptide backbone and that both (1R)-16 and (1S)-16 cyclized smoothly to provide the corresponding macrocycle. On the other hand, dehydration of the secondary benzylic alcohol, via the phenylselenide intermediate, is configuration dependent. (1R)-25 underwent the two-step syn-elimination much more easily than (1S)-22. A modified reductive deamination procedure via the diazonium intermediate was developed. A complete assignment of proton and carbon NMR spectroscopy signals for these natural products is reported for the first time.
[reaction: see text] A tandem Michael addition-enolate alkylation followed by Dieckmann cyclization and Beckmann rearrangement provided the corresponding [5.4.0] azaspirobicyclodecane, a key intermediate in our synthetic route to the marine alkaloid halichlorine (1).