Discovery and Biomimetic Semisynthesis of Spirophyllines A-D from Uncaria rhynchophylla.
Org Lett
; 25(24): 4434-4438, 2023 06 23.
Article
em En
| MEDLINE
| ID: mdl-37288843
ABSTRACT
Spirophyllines A-D (1-4), four new spirooxindole alkaloids all characterized by the spiro[pyrrolidin-3,3'-oxindole] core and a rare isoxazolidine ring, were isolated from Uncaria rhynchophylla. Their structures were determined by spectroscopic methods and confirmed by X-ray crystallography. Based on the biomimetic semisynthesis strategy, compounds 1-8 were synthesized in three steps via the key reactions of 1,3-dipolar cycloaddition and Krapcho decarboxylation from corynoxeine. Interestingly, compound 3 showed moderate inhibitory activity against the Kv1.5 potassium channel (IC50 = 9.1 µM).
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Coleções:
01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
2023
Tipo de documento:
Article