Diastereoselective Synthesis of Novel Spiro-Phosphacoumarins and Evaluation of Their Anti-Cancer Activity.
anti-cancer
azomethine ylide
cycloaddition
cytotoxicity
phosphacoumarin
quantum chemistry
Journal
International journal of molecular sciences
ISSN: 1422-0067
Titre abrégé: Int J Mol Sci
Pays: Switzerland
ID NLM: 101092791
Informations de publication
Date de publication:
18 Nov 2022
18 Nov 2022
Historique:
received:
27
10
2022
revised:
14
11
2022
accepted:
15
11
2022
entrez:
26
11
2022
pubmed:
27
11
2022
medline:
30
11
2022
Statut:
epublish
Résumé
Herein we present the regio- and diastereoselective synthesis of novel pyrrolidine-fused spiro-dihydrophosphacoumarins via intermolecular [3 + 2] cycloaddition reaction. The presented approach is complementary to existing ones and provides an easy entry to the otherwise inaccessible derivatives. Additionally, the unprecedented pathway of the reaction of 4-hydroxycoumarin with azomethine ylides is described. The anti-cancer activity of the obtained compounds was tested in vitro, the most potent compound being 2.6-fold more active against the HuTu 80 cell line than the reference 5-fluorouracil, with a selectivity index > 32.
Identifiants
pubmed: 36430824
pii: ijms232214348
doi: 10.3390/ijms232214348
pmc: PMC9695012
pii:
doi:
Substances chimiques
Spiro Compounds
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : FRC Kazan Scientific Center of RAS
Organisme : Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences
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