Enantiomeric 4-Acylamino-6-alkyloxy-2 Alkylthiopyrimidines As Potential A3 Adenosine Receptor Antagonists: HPLC Chiral Resolution and Absolute Configuration Assignment by a Full Set of Chiroptical Spectroscopy
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- 作者：Daniela Rossi ; Rita Nasti ; Annamaria Marra ; Silvia Meneghini ; Giuseppe Mazzeo ; Giovanna Longhi ; Maurizio Memo ; Barbara Cosimelli ; Giovanni Greco ; Ettore Novellino ; Federico Da Settimo ; Claudia Martini ; Sabrina Taliani ; Sergio Abbate and Simona Collina
- 关键词：A3 adenosine receptor antagonists ; chiral HPLC ; optical rotatory dispersion (ORD) ; electronic circular dichroism (ECD) ; vibrational circular dichroism (VCD) ; Density Functional Theory (DFT) ; absolute configuration assignment
- 刊名：Chirality
- 出版年：2016
- 出版时间：May 2016
- 年：2016
- 卷：28
- 期：5
- 页码：434-440
- 全文大小：285K
- ISSN：1520-636X
文摘
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 (1), (R/S)-N-(2-(1-phenylethylthio)-6-propoxypyrimidin-4-yl)acetamide (2), and (R/S)-N-(2-(benzylthio)-6-sec-butoxypyrimidin-4-yl)acetamide (3) 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.