A Novel Class of N-Sulfonyl and N-Sulfamoyl Noscapine Derivatives that Promote Mitotic Arrest in Cancer Cells.
ATP Binding Cassette Transporter, Subfamily B, Member 1
/ metabolism
Antineoplastic Agents
/ chemical synthesis
Cell Line, Tumor
Cell Proliferation
/ drug effects
Drug Screening Assays, Antitumor
Humans
Microtubules
/ metabolism
Molecular Structure
Noscapine
/ analogs & derivatives
Polymerization
Structure-Activity Relationship
Sulfuric Acids
/ chemistry
Tubulin
/ metabolism
anticancer agents
antimitotic agents
microtubule targeting agents
natural products
noscapine derivatives
Journal
ChemMedChem
ISSN: 1860-7187
Titre abrégé: ChemMedChem
Pays: Germany
ID NLM: 101259013
Informations de publication
Date de publication:
04 12 2019
04 12 2019
Historique:
received:
15
08
2019
revised:
12
10
2019
pubmed:
13
11
2019
medline:
17
9
2020
entrez:
13
11
2019
Statut:
ppublish
Résumé
Noscapine displays weak anticancer efficacy and numerous research efforts have attempted to generate more potent noscapine analogues. These modifications included the replacement of the N-methyl group in the 6'-position with a range of substituents, where N-ethylcarbamoyl substitution was observed to possess enhanced anticancer activity. Herein, we describe advances in this area, namely the synthesis and pharmacological evaluation of a series of N-sulfonyl and N-sulfamoyl noscapine derivatives. A number of these sulfonyl-containing noscapinoids demonstrated improved activities compared to noscapine. ((R)-5-((S)-4,5-Dimethoxy-1,3-dihydroisobenzofuran-1-yl)-4-methoxy-6-((1-methyl-1H-imidazol-4-yl)sulfonyl)-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline) (14 q) displayed sub-micromolar activities of 560, 980, 271 and 443 nM against MCF-7, PANC-1, MDA-MB-435 and SK-MEL-5 cells, respectively. This antiproliferative effect was also maintained against drug-resistant NCI/Adr
Identifiants
pubmed: 31714012
doi: 10.1002/cmdc.201900477
doi:
Substances chimiques
ATP Binding Cassette Transporter, Subfamily B, Member 1
0
Antineoplastic Agents
0
Sulfuric Acids
0
Tubulin
0
Noscapine
8V32U4AOQU
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
1968-1981Subventions
Organisme : Australian government
Pays : International
Organisme : Australian Postgraduate Award
Pays : International
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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