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Open AccessArticle

Structural and Conformational Studies on Carboxamides of 5,6-Diaminouracils—Precursors of Biologically Active Xanthine Derivatives

1
Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, D-53121 Bonn, Germany
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Pharma Center Bonn, University of Bonn, D-53121 Bonn, Germany
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Department of Chemistry, Institute of Inorganic Chemistry, University of Bonn, D-53121 Bonn, Germany
4
Mulliken Center for Theoretical Chemistry, Institute of Physical and Theoretical Chemistry, University of Bonn, D-53115 Bonn, Germany
*
Author to whom correspondence should be addressed.
Academic Editor: F. Javier Luque
Molecules 2019, 24(11), 2168; https://doi.org/10.3390/molecules24112168
Received: 2 May 2019 / Revised: 2 June 2019 / Accepted: 4 June 2019 / Published: 9 June 2019
(This article belongs to the Section Medicinal Chemistry)
8-Arylethynylxanthine derivatives are potent, selective adenosine A2A receptor antagonists, which represent (potential) therapeutics for Parkinson’s disease, Alzheimer’s dementia, and the immunotherapy of cancer. 6-Amino-5-amidouracil derivatives are important precursors for the synthesis of such xanthines. We noticed an unexpected duplication of NMR signals in many of these uracil derivatives. Here, we present a detailed analytical study of structurally diverse 6-amino-5-carboxamidouracils employing dynamic and two-dimensional NMR spectroscopy, density functional theory calculations, and X-ray analysis to explain the unexpected properties of these valuable drug intermediates. View Full-Text
Keywords: amide; DFT calculation; dynamic NMR; rotamers/conformers; uracil; xanthine; X-ray crystallography amide; DFT calculation; dynamic NMR; rotamers/conformers; uracil; xanthine; X-ray crystallography
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Marx, D.; Schnakenburg, G.; Grimme, S.; Müller, C.E. Structural and Conformational Studies on Carboxamides of 5,6-Diaminouracils—Precursors of Biologically Active Xanthine Derivatives. Molecules 2019, 24, 2168.

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