Light-promoted stereoselective late-stage difunctionalization and anti-tumor activity of oridonin.
Fitoterapia
; 177: 106131, 2024 Sep.
Article
em En
| MEDLINE
| ID: mdl-39067489
ABSTRACT
The late-stage difunctionalization of diterpene oridonin by light-promoted direct oxyamination with various O-benzoylhydroxylamines was carried out to afford C16α-N-C17-OBz-oridonin derivatives (1-25) for the first time. Though as a radical reaction, it features high stereoselectivity to only produce C16α-N-C17-OBz-oridonins. The in vitro antiproliferative activity of these C16α-N-C17-OBz-oridonins against the human breast cancer cell lines (MCF-7) was evaluated by MTT assay, showing that most of the synthesized compounds possessed moderate anticancer activity against MCF-7 cell lines superior or similar to the parent compound oridonin. The derivative 25 with a N-methyl-N-(naphthalen-1-ylmethyl) substitution showed better cytotoxicity against MCF-7 cells (IC50 value of 11.75 µM) than oridonin (IC50 value of 17.95 µM).
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Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Diterpenos do Tipo Caurano
/
Antineoplásicos Fitogênicos
Limite:
Humans
Idioma:
En
Revista:
Fitoterapia
Ano de publicação:
2024
Tipo de documento:
Article