1,3-Benzodioxole-Modified Noscapine Analogues: Synthesis, Antiproliferative Activity, and Tubulin-Bound Structure.
Antineoplastic Agents
/ chemical synthesis
Cell Proliferation
/ drug effects
Dioxoles
/ chemical synthesis
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
Molecular Structure
Polymerization
/ drug effects
Structure-Activity Relationship
Tubulin
/ metabolism
Tubulin Modulators
/ chemical synthesis
Tumor Cells, Cultured
anti-cancer agents
anti-mitotic agents
microtubule targeting agents
noscapine derivatives
Journal
ChemMedChem
ISSN: 1860-7187
Titre abrégé: ChemMedChem
Pays: Germany
ID NLM: 101259013
Informations de publication
Date de publication:
16 09 2021
16 09 2021
Historique:
received:
24
05
2021
pubmed:
24
6
2021
medline:
17
2
2022
entrez:
23
6
2021
Statut:
ppublish
Résumé
Since the revelation of noscapine's weak anti-mitotic activity, extensive research has been conducted over the past two decades, with the goal of discovering noscapine derivatives with improved potency. To date, noscapine has been explored at the 1, 7, 6', and 9'-positions, though the 1,3-benzodioxole motif in the noscapine scaffold that remains unexplored. The present investigation describes the design, synthesis and pharmacological evaluation of noscapine analogues consisting of modifications to the 1,3-benzodioxole moiety. This includes expansion of the dioxolane ring and inclusion of metabolically robust deuterium and fluorine atoms. Favourable structural modifications were subsequently incorporated into multi-functionalised noscapine derivatives that also possessed modifications previously shown to promote anti-proliferative activity in the 1-, 6'- and 9'-positions. Our research efforts afforded the deuterated noscapine derivative 14 e and the dioxino-containing analogue 20 as potent cytotoxic agents with EC
Identifiants
pubmed: 34159741
doi: 10.1002/cmdc.202100363
doi:
Substances chimiques
Antineoplastic Agents
0
Dioxoles
0
Tubulin
0
Tubulin Modulators
0
1,3-benzodioxole
F0XLL582B8
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
2882-2894Subventions
Organisme : Australian government
Organisme : Australian Postgraduate Award to CY
Organisme : National Cancer Institute (NCI)
Organisme : H2020-MSCA-ITN-2019
ID : 860070 TUBINTRAIN
Organisme : Swiss National Science Foundation
ID : 310030_192566
Pays : Switzerland
Informations de copyright
© 2021 Wiley-VCH GmbH.
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