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Regioselective Halogenations and Subsequent Suzuki-Miyaura Coupling onto Bicyclic 2-Pyridones
Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
2010 (Engelska)Ingår i: The Journal of organic chemistry, ISSN 1520-6904, Vol. 75, nr 3, s. 972-5Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

A selective synthesis of 6-bromo-8-iodo dihydro thiazolo ring-fused 2-pyridones is described. These halogenated 2-pyridones are selectively arylated by sequential Suzuki-Miyaura couplings. This approach can advantageously be used to synthesize focused libraries of substituted ring-fused 2-pyridones, a class of compounds with novel antibacterial properties.

Ort, förlag, år, upplaga, sidor
American Chemical Society , 2010. Vol. 75, nr 3, s. 972-5
Identifikatorer
URN: urn:nbn:se:umu:diva-30482DOI: 10.1021/jo902458gISI: 000273982900059PubMedID: 20025251OAI: oai:DiVA.org:umu-30482DiVA, id: diva2:284072
Tillgänglig från: 2010-01-04 Skapad: 2010-01-04 Senast uppdaterad: 2018-06-08Bibliografiskt granskad
Ingår i avhandling
1. Synthesis of substituted Ring-Fused 2-Pyridones and applications in chemical biology
Öppna denna publikation i ny flik eller fönster >>Synthesis of substituted Ring-Fused 2-Pyridones and applications in chemical biology
2013 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
Abstract [en]

Antibiotics have been extensively used to treat bacterial infections since Alexander Fleming’s discovery of penicillin 1928. Disease causing microbes that have become resistant to antibiotic drug therapy are an increasing public health problem. According to the world health organization (WHO) there are about 440 000 new cases of multidrug-resistant tuberculosis emerging annually, causing at least 150 000 deaths. Consequently there is an immense need to develop new types of compounds with new modes of action for the treatment of bacterial infections.

Presented herein is a class of antibacterial ring-fused 2-pyridones, which exhibit inhibitory effects against both the pili assembly system in uropathogenic Escherichia coli (UPEC), named the chaperone usher pathway, as well as polymerization of the major curli subunit protein CsgA, into a functional amyloid fibre. A pilus is an organelle that is vital for the bacteria to adhere to and infect host cells, as well as establish biofilms. Inhibition of the chaperone usher pathway disables the pili assembly machinery, and consequently renders the bacteria avirulent.

The focus of this work has been to develop synthetic strategies to more efficiently alter the substitution pattern of the aforementioned ring-fused 2-pyridones. In addition, asymmetric routes to enantiomerically enriched key compounds and routes to compounds containing BODIPY and coumarin fluorophores as tools to study bacterial virulence mechanisms have been developed. Several of the new compounds have successfully been evaluated as antibacterial agents. In parallel with this research, manipulations of the core structure to create new heterocycle based central fragments for applications in medicinal chemistry have also been performed.   

Ort, förlag, år, upplaga, sidor
Umeå: Umeå universitet, 2013. s. 85
Nyckelord
Synthesis, 2-pyridone, 2-thiazoline, cross coupling, pili, curli, antibacterial
Nationell ämneskategori
Naturvetenskap
Forskningsämne
organisk kemi
Identifikatorer
urn:nbn:se:umu:diva-68709 (URN)978-91-7459-552-9 (ISBN)
Disputation
2013-05-24, KBC-Huset, KB3B1, Umeå universitet, Umeå, 10:00 (Engelska)
Opponent
Handledare
Tillgänglig från: 2013-05-03 Skapad: 2013-04-23 Senast uppdaterad: 2018-06-08Bibliografiskt granskad

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Bengtsson, ChristofferAlmqvist, Fredrik

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