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A three-component reaction forming naphthyridones: synthesis of lophocladine analogs
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
2011 (Engelska)Ingår i: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 13, nr 19, s. 5278-5281Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

A three-component reaction forming dihydro 2,7-naphthyridine-1-ones has been developed. These unstable dihydro intermediates can be either oxidized or reduced to form naphthyridones or tetrahydro naphthyridones, respectively. The reaction tolerates a large variety of aldehydes and amines, and the produced compounds are analogs of the natural product lophocladine A.

Ort, förlag, år, upplaga, sidor
Washington, D.C.: American Chemical Society , 2011. Vol. 13, nr 19, s. 5278-5281
Nationell ämneskategori
Organisk kemi
Identifikatorer
URN: urn:nbn:se:umu:diva-49229DOI: 10.1021/ol202080xISI: 000295313900077OAI: oai:DiVA.org:umu-49229DiVA, id: diva2:455768
Tillgänglig från: 2011-11-11 Skapad: 2011-11-04 Senast uppdaterad: 2018-06-08Bibliografiskt granskad
Ingår i avhandling
1. Development of 2-Pyridone-based central fragments: Affecting the aggregation of amyloid proteins
Öppna denna publikation i ny flik eller fönster >>Development of 2-Pyridone-based central fragments: Affecting the aggregation of amyloid proteins
2012 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
Abstract [en]

There are many applications of small organic compounds, e.g. as drugs or as tools to study biological systems. Once a compound with interesting biological activity has been found, medicinal chemists typically synthesize small libraries of compounds with systematic differences to the initial “hit” compound. By screening the new ensemble of compounds for their ability to perturb the biological system, insights about the system can be gained. In the work presented here, various ways to synthesize small libraries of ring-fused 2‑pyridones have been developed. Members of this class of peptidomimetic compounds have previously been found to have a variety of biological activities, e.g. as antibacterial agents targeting virulence, and as inhibitors of the aggregation of Alzheimer b‑peptides. The focus in this work has been to alter the core skeleton, the central fragment, of the previously discovered biologically active 2‑pyridones and evaluate the biological effects of these changes. Several new classes of compounds have been constructed and their preparations have included the development of multi-component reactions and a method inspired by diversity-oriented synthesis.

Some of the new compounds have been evaluated for their effect on the fibrillation of different amyloid proteins. Both the Parkinson-associated amyloid protein a-synuclein and the bacterial protein CsgA that is involved in bacterial biofilm formation are affected by subtle changes of the compounds’ central fragments. This is an example of the usefulness of central-fragment alterations as a strategy to probe structure-activity relationships, and the derived compounds may be used as tools in further study of the aggregation of amyloid proteins.

Ort, förlag, år, upplaga, sidor
Umeå, Sweden: Umeå universitet, 2012. s. 60
Nyckelord
2-pyridone, central fragment alteration, multi-component reactions, directed diversity-oriented synthesis, peptidomimetics, amyloid, protein aggregation, pilicide, curlicide
Nationell ämneskategori
Organisk kemi
Forskningsämne
bioorganisk kemi
Identifikatorer
urn:nbn:se:umu:diva-53705 (URN)978-91-7459-417-1 (ISBN)
Disputation
2012-04-27, KBC-huset, KB3B1, Umeå universitet, Umeå, 10:00 (Engelska)
Opponent
Handledare
Forskningsfinansiär
Vetenskapsrådet, 621-2010-4730Knut och Alice Wallenbergs Stiftelse
Tillgänglig från: 2012-04-05 Skapad: 2012-04-04 Senast uppdaterad: 2018-06-08Bibliografiskt granskad

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Sellstedt, MagnusAlmqvist, Fredrik

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