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 | Zendy

Rossi Daniela | Zendy; Nasti Rita | Zendy; Marra Annamaria | Zendy; Meneghini Silvia | Zendy; Mazzeo Giuseppe | Zendy; Longhi Giovanna | Zendy; Memo Maurizio | Zendy; Cosimelli Barbara | Zendy; Greco Giovanni | Zendy; Novellino Ettore | Zendy; Da Settimo Federico | Zendy; Martini Claudia | Zendy; Taliani Sabrina | Zendy; Abbate Sergio | Zendy; Collina Simona | Zendy

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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 , absolute configuration , enantiomer , chiral column chromatography , resolution (logic) , stereochemistry , spectroscopy , circular dichroism , enantiomeric excess , high performance liquid chromatography , chirality (physics) , stereoselectivity , chromatography , organic chemistry , enantioselective synthesis , catalysis , chiral symmetry , physics , nambu–jona lasinio model , quantum mechanics , artificial intelligence , quark , computer science

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.

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