Construction of Diversified Penta-Spiro-Heterocyclic and Fused-Heterocyclic Frameworks with Potent Antitumor Activity.
C−H activation/ [4+1] and [4+2] annulation
antitumor
indazolone
spiro/fused-heterocyclic frameworks
substrate- and pH- controlled strategies
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
26 Sep 2023
26 Sep 2023
Historique:
received:
20
05
2023
medline:
28
9
2023
pubmed:
28
6
2023
entrez:
27
6
2023
Statut:
ppublish
Résumé
Multiple-spiro/fused-heterocyclic frameworks containing indazolone are structurally unique and represent a class of potentially dominant skeletons. In this work, we successfully fulfilled Rh(III)-catalyst mediated substrate- and pH- controlled strategies to construct four novel types of complicated penta-spiro/fused-heterocyclic frameworks via C-H activation/[4+1] and [4+2] annulation cascades. This method had mild reaction conditions, a broad scope of substrates, moderate to good yields, and valuable applications, which could realize for the first time the generation of the novel di-spiro-heterocyclic and multiple fused-heterocyclic products with unique structures. More importantly, novel spiro[cyclohexane-indazolo[1,2-a]indazole] scaffold constructed by this method exhibited potent antitumor activity against a variety of refractory solid tumors and hematological malignancies in vitro. Overall, our work provided new insights into the construction of complex and diverse multiple spiro/fused-heterocyclic systems and offered novel valuable lead compounds for the discovery of antitumor drugs.
Identifiants
pubmed: 37370192
doi: 10.1002/chem.202301553
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202301553Subventions
Organisme : National Natural Science Foundation of China
ID : 21907102, 82130105, 82173656
Organisme : Lingang Laboratory
ID : LG202103-02-07, LG-QS-202205-09
Informations de copyright
© 2023 Wiley-VCH GmbH.
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