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Adolfsson, Dan E.
Publikasjoner (2 av 2) Visa alla publikasjoner
Singh, P., Adolfsson, D. E., Ådén, J., Cairns, A. G., Bartens, C., Brännström, K., . . . Almqvist, F. (2019). Pyridine-Fused 2-Pyridones via Povarov and A3 Reactions: Rapid Generation of Highly Functionalized Tricyclic Heterocycles Capable of Amyloid Fibril Binding. Journal of Organic Chemistry, 84(7), 3887-3903
Åpne denne publikasjonen i ny fane eller vindu >>Pyridine-Fused 2-Pyridones via Povarov and A3 Reactions: Rapid Generation of Highly Functionalized Tricyclic Heterocycles Capable of Amyloid Fibril Binding
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2019 (engelsk)Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 84, nr 7, s. 3887-3903Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

We here describe the use of three-component reactions to synthesize tricyclic pyridine ring-fused 2-pyridones. The developed protocols have a wide substrate scope and allow for the installation of diverse chemical functionalities on the tricyclic central fragment. Several of these pyridine-fused rigid polyheterocycles are shown to bind to Aβ and α-synuclein fibrils, which are associated with neurodegenerative diseases.

sted, utgiver, år, opplag, sider
American Chemical Society (ACS), 2019
HSV kategori
Identifikatorer
urn:nbn:se:umu:diva-157464 (URN)10.1021/acs.joc.8b03015 (DOI)000464250800014 ()30862161 (PubMedID)
Forskningsfinansiär
Swedish Research Council, 2014-04673Swedish Research Council, 2018-04589Knut and Alice Wallenberg Foundation, KAW 2013.0031The Kempe Foundations, SMK-1755Swedish Foundation for Strategic Research , SB12-0070
Tilgjengelig fra: 2019-03-21 Laget: 2019-03-21 Sist oppdatert: 2019-06-13bibliografisk kontrollert
Singh, P., Cairns, A. G., Adolfsson, D. E., Ådén, J., Sauer, U. H. & Almqvist, F. (2019). Synthesis of Densely Functionalized N-Alkenyl 2-Pyridones via Benzyne-Induced Ring Opening of Thiazolino-Fused 2-Pyridones. Organic Letters, 21, 6946-6950
Åpne denne publikasjonen i ny fane eller vindu >>Synthesis of Densely Functionalized N-Alkenyl 2-Pyridones via Benzyne-Induced Ring Opening of Thiazolino-Fused 2-Pyridones
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2019 (engelsk)Inngår i: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 21, s. 6946-6950Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

We report the synthesis of 6-arylthio-substituted-N-alkenyl 2-pyridones by ring opening of bicyclic thiazolino-2-pyridones with arynes. Varied functionalization was used to investigate scope and substituent influences on reactivity. Selected conditions favor thioether ring opening over [4 + 2] cycloaddition and an unusual aryne incorporating ring expansion. Deuterium labeling was used to clarify observed reactivity. Using the knowledge, we produced drug-like molecules with complex substitution patterns and show how thioether ring opening can be used on scaffolds with competing reactivities.

sted, utgiver, år, opplag, sider
American Chemical Society (ACS), 2019
HSV kategori
Identifikatorer
urn:nbn:se:umu:diva-162826 (URN)10.1021/acs.orglett.9b02549 (DOI)000485089300073 ()31419146 (PubMedID)2-s2.0-85071698867 (Scopus ID)
Tilgjengelig fra: 2019-08-30 Laget: 2019-08-30 Sist oppdatert: 2019-11-13bibliografisk kontrollert
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