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Enantiomeric 4‐Acylamino‐6‐alkyloxy‐2 Alkylthiopyrimidines As Potential A 3 Adenosine Receptor Antagonists: HPLC Chiral Resolution and Absolute Configuration Assignment by a Full Set of Chiroptical Spectroscopy
Author(s) -
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
Publication year - 2016
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22599
Subject(s) - chemistry , circular dichroism , enantiomer , acetamide , absolute configuration , chirality (physics) , vibrational circular dichroism , optical rotatory dispersion , chiral column chromatography , resolution (logic) , stereochemistry , high performance liquid chromatography , chromatography , organic chemistry , chiral symmetry , physics , quantum mechanics , artificial intelligence , computer science , nambu–jona lasinio model , quark
The chiral separation of enantiomeric couples of three potential A 3 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 . © 2016 Wiley Periodicals, Inc.