| Literature DB >> 27095007 |
Daniela Rossi1, Rita Nasti1, Annamaria Marra1, Silvia Meneghini1,2, Giuseppe Mazzeo2, Giovanna Longhi2, Maurizio Memo2, Barbara Cosimelli3, Giovanni Greco3, Ettore Novellino3, Federico Da Settimo4, Claudia Martini4, Sabrina Taliani4, Sergio Abbate2, Simona Collina1.
Abstract
The chiral separation of enantiomeric couples of three potential A3 adenosine receptor antagonists: (R/S)-N-(6-(1-phenylethoxy)-2-(propylthio)pyrimidin-4-yl)acetamide (), (R/S)-N-(2-(1-phenylethylthio)-6-propoxypyrimidin-4-yl)acetamide (), and (R/S)-N-(2-(benzylthio)-6-sec-butoxypyrimidin-4-yl)acetamide () was achieved by high-performance liquid chromatography (HPLC). Three types of chiroptical spectroscopies, namely, optical rotatory dispersion (ORD), electronic circular dichroism (ECD), and vibrational circular dichroism (VCD), were applied to enantiomeric compounds. Through comparison with Density Functional Theory (DFT) calculations, encompassing extensive conformational analysis, full assignment of the absolute configuration (AC) for the three sets of compounds was obtained. Chirality 28:434-440, 2016.Entities:
Keywords: A3 adenosine receptor antagonists; Density Functional Theory (DFT); absolute configuration assignment; chiral HPLC; electronic circular dichroism (ECD); optical rotatory dispersion (ORD); vibrational circular dichroism (VCD)
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Year: 2016 PMID： 27095007 DOI： 10.1002/chir.22599
Source DB: PubMed Journal: Chirality ISSN： 0899-0042 Impact factor: 2.437