对映体4-酰氨基-6-烷氧基-2-烷基硫代嘧啶作为潜在的A3腺苷受体拮抗剂：通过全套手性光谱进行高效液相色谱手性拆分和绝对构型确定
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.
作者信息
Rossi Daniela, Nasti Rita, Marra Annamaria, Meneghini Silvia, Mazzeo Giuseppe, Longhi Giovanna, Memo Maurizio, Cosimelli Barbara, Greco Giovanni, Novellino Ettore, Da Settimo Federico, Martini Claudia, Taliani Sabrina, Abbate Sergio, Collina Simona
机构信息
Dipartimento di Scienze del Farmaco, Università di Pavia, Pavia, Italy.
Dipartimento di Medicina Molecolare e Traslazionale, Università di Brescia, Brescia, Italy.
出版信息
Chirality. 2016 May;28(5):434-40. doi: 10.1002/chir.22599. Epub 2016 Apr 20.
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. © 2016 Wiley Periodicals, Inc.
三种潜在的A3腺苷受体拮抗剂对映体对：(R/S)-N-(6-(1-苯乙氧基)-2-(丙硫基)嘧啶-4-基)乙酰胺（）、(R/S)-N-(2-(1-苯乙硫基)-6-丙氧基嘧啶-4-基)乙酰胺（）和(R/S)-N-(2-(苄硫基)-6-仲丁氧基嘧啶-4-基)乙酰胺（）的手性拆分通过高效液相色谱法（HPLC）实现。三种手性光学光谱，即旋光色散（ORD）、电子圆二色性（ECD）和振动圆二色性（VCD），被应用于对映体化合物。通过与包含广泛构象分析的密度泛函理论（DFT）计算进行比较，获得了三组化合物绝对构型（AC）的完全归属。《手性》28:434 - 440，2016年。© 2016威利期刊公司。
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