Synthesis and Cytotoxic Activity of Chiral Sulfonamides Based on the 2-Azabicycloalkane Skeleton.

Tytuł:: Synthesis and Cytotoxic Activity of Chiral Sulfonamides Based on the 2-Azabicycloalkane Skeleton.
Autorzy:: Samadaei M; Department of Internal Medicine III, Medical University of Vienna, AKH Vienna Währinger Gürtel 18-20, 1090 Vienna, Austria.
Pinter M; Department of Internal Medicine III, Medical University of Vienna, AKH Vienna Währinger Gürtel 18-20, 1090 Vienna, Austria.
Senfter D; Department of Internal Medicine III, Medical University of Vienna, AKH Vienna Währinger Gürtel 18-20, 1090 Vienna, Austria.
Madlener S; Department of Internal Medicine III, Medical University of Vienna, AKH Vienna Währinger Gürtel 18-20, 1090 Vienna, Austria.
Rohr-Udilova N; Department of Internal Medicine III, Medical University of Vienna, AKH Vienna Währinger Gürtel 18-20, 1090 Vienna, Austria.
Iwan D; Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland.
Kamińska K; Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland.
Wojaczyńska E; Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland.
Wojaczyński J; Faculty of Chemistry, University of Wrocław, F. Joliot-Curie St. 14, 50-383 Wrocław, Poland.
Kochel A; Faculty of Chemistry, University of Wrocław, F. Joliot-Curie St. 14, 50-383 Wrocław, Poland.
Źródło:: Molecules (Basel, Switzerland) [Molecules] 2020 May 18; Vol. 25 (10). Date of Electronic Publication: 2020 May 18.
Typ publikacji:: Journal Article
Język:: English
Imprint Name(s):: Original Publication: Basel, Switzerland : MDPI, c1995-
MeSH Terms:: Alkanes/*chemistry
Carcinoma, Hepatocellular/*drug therapy
Liver Neoplasms/*drug therapy
Sulfonamides/*chemistry
Alkanes/chemical synthesis ; Alkanes/pharmacology ; Amines/chemical synthesis ; Amines/chemistry ; Amines/pharmacology ; Carcinoma, Hepatocellular/pathology ; Humans ; Liver Neoplasms/pathology ; Molecular Structure ; Stereoisomerism ; Sulfonamides/chemical synthesis ; Sulfonamides/pharmacology
References:: ChemMedChem. 2017 Aug 22;12(16):1380-1389. (PMID: 28665505)
Nat Rev Drug Discov. 2012 Oct;11(10):751-61. (PMID: 22935759)
Int J Cancer. 2015 Mar 1;136(5):E359-86. (PMID: 25220842)
Curr Chem Genom Transl Med. 2018 Jun 29;12:9-26. (PMID: 30069430)
Bioorg Med Chem Lett. 2005 Nov 1;15(21):4761-9. (PMID: 16112571)
Molecules. 2016 Mar 25;21(4):409. (PMID: 27023509)
Medchemcomm. 2014 Sep 1;5(9):1317-1323. (PMID: 25328661)
BMC Cancer. 2009 Jan 10;9:10. (PMID: 19134217)
Anticancer Res. 2019 Jul;39(7):3423-3427. (PMID: 31262865)
Br J Cancer. 2008 Jul 8;99(1):151-9. (PMID: 18594539)
Org Biomol Chem. 2015 Jun 14;13(22):6116-48. (PMID: 25901970)
Med Res Rev. 2003 Sep;23(5):535-58. (PMID: 12789686)
J Biotechnol. 2016 Oct 20;236:10-25. (PMID: 27498314)
Mol Nutr Food Res. 2008 Mar;52(3):352-9. (PMID: 18293301)
Acta Crystallogr C Struct Chem. 2015 Jan;71(Pt 1):3-8. (PMID: 25567568)
J Med Chem. 2015 Oct 8;58(19):7749-62. (PMID: 26393416)
Contributed Indexing:: Keywords: 2-azabicycloalkane; chiral sulfonamide; cytotoxic activity
Substance Nomenclature:: 0 (Alkanes)
0 (Amines)
0 (Sulfonamides)
Entry Date(s):: Date Created: 20200524 Date Completed: 20210211 Latest Revision: 20240328
Update Code:: 20240329
PubMed Central ID:: PMC7288168
DOI:: 10.3390/molecules25102355
PMID:: 32443610
: Czasopismo naukowe

Pełny tekst

A series of chiral sulfonamides containing the 2-azabicycloalkane scaffold were prepared from aza -Diels-Alder cycloadducts through their conversion to amines based on 2-azanorbornane or the bridged azepane skeleton, followed by the reaction with sulfonyl chlorides. The cytotoxic activity of the obtained bicyclic derivatives was evaluated using human hepatocellular carcinoma (HCC), medulloblastoma (MB), and glioblastoma (GBM) cell lines. Chosen compounds were shown to notably reduce cell viability as compared to nonmalignant cells.

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