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Synthesis of functionalized furopyrazines as restricted dipeptidomimetics
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
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2012 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 68, no 14, 3019-3029 p.Article in journal (Refereed) Published
Abstract [en]

Herein, an efficient synthetic approach to a furopyrazine scaffold with four points of diversity, starting from 2(1H)-pyrazinones, with dipeptomimetic properties, is presented. R-groups corresponding to amino acid side chains were introduced during the 2(1H)-pyrazinone and subsequent furopyrazine formation. The furopyrazine scaffold was further functionalized with an amino- and a carboxy-terminus resulting in a conformationally restricted dipeptidomimetic scaffold. The carboxy-terminus was introduced via a chemoselective vinylation of the 7-position followed by oxidative cleavage, while the amino-terminus was obtained via Buchwald-Hartwig amidation of the 2-position of the scaffold. The versatility of the synthetic method was demonstrated by the synthesis of a small library of diversely substituted furopyrazines having various amino acid side chains on the four points of diversity. Evaluation with an X-ray structure of the scaffold and computational analysis supports the exploitation of the furopyrazine scaffold as a restricted dipeptide mimic, which can mimic the two central residues of a beta-turn.

Place, publisher, year, edition, pages
2012. Vol. 68, no 14, 3019-3029 p.
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Natural Sciences
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URN: urn:nbn:se:uu:diva-173984DOI: 10.1016/j.tet.2012.02.022ISI: 000302451100010OAI: oai:DiVA.org:uu-173984DiVA: diva2:526630
Available from: 2012-05-14 Created: 2012-05-09 Last updated: 2017-12-07Bibliographically approved

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Sköld, ChristianSandström, AnjaLarhed, Mats

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