Synthesis and Biological Evaluation of (-) and (+)-Spiroleucettadine and Analogues.
alkaloids
hypervalent iodine
medicinal chemistry
oxidative spirocyclization
total synthesis
Journal
ChemMedChem
ISSN: 1860-7187
Titre abrégé: ChemMedChem
Pays: Germany
ID NLM: 101259013
Informations de publication
Date de publication:
20 04 2021
20 04 2021
Historique:
received:
21
01
2021
pubmed:
16
12
2020
medline:
12
1
2022
entrez:
15
12
2020
Statut:
ppublish
Résumé
A second-generation enantiospecific synthesis of spiroleucettadine is described. The original reported antibacterial activity was not observed when the experiment was repeated on the synthetic samples; however, significant anti-proliferative activity was uncovered for both enantiomers of spiroleucettadine. Comparison of the optical rotational data and ORD-CD spectra of both enantiomers and the reported spectrum from the natural source have not provided a definitive answer regarding the absolute stereochemistry of naturally occurring spiroleucettadine. Efforts then focussed on alteration at the C-4 and C-5 positions of the slightly more active (-)-spiroleucettadine. Ten analogues were synthesised, with three analogues found to possess similar anti-proliferative profiles to spiroleucettadine against the H522 lung cancer cell line.
Identifiants
pubmed: 33320428
doi: 10.1002/cmdc.202000954
doi:
Substances chimiques
Antineoplastic Agents
0
Imidazoles
0
Spiro Compounds
0
spiroleucettadine
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
1308-1315Subventions
Organisme : University of Otago for a Research grant (UORG)
Informations de copyright
© 2020 Wiley-VCH GmbH.
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