{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,29]],"date-time":"2026-04-29T04:09:45Z","timestamp":1777435785660,"version":"3.51.4"},"reference-count":25,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2008,8,12]],"date-time":"2008-08-12T00:00:00Z","timestamp":1218499200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chirality"],"published-print":{"date-parts":[[2009,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The normal phase mode liquid chromatographic enantiomer separation capability of a quinine <jats:italic>tert<\/jats:italic>\u2010butyl\u2010carbamate\u2010type chiral stationary phase (CSP) has been investigated for a set of polar [1,5\u2010b]\u2010quinazoline\u20101,5\u2010dione derivatives. This class of chiral heterocycles is currently under development as potential \u03b1\u2010amino\u20103\u2010hydroxy\u20105\u2010methyl\u20104\u2010isoxazole propionic acid (AMPA) and\/or <jats:italic>N<\/jats:italic>\u2010methyl\u2010<jats:sc>D<\/jats:sc>\u2010aspartic acid (NMDA) receptor antagonists. The effect of the nature and concentration of polar modifier, i.e., ethanol and isopropanol, in <jats:italic>n<\/jats:italic>\u2010hexane\u2010based mobile phases, as well as the substituent pattern of the phenyl ring attached to the quinazolone framework on retention factor, enantioselectivity, and resolution was investigated. The Soczewi\u0144ski competitive adsorption model was used to describe the relationship between the retention and the binary mobile phase compositions. According to this model, linear plots of the logarithms of retention factor versus molar fractions of the polar modifiers were obtained over a wide concentration range (<jats:italic>X<\/jats:italic><jats:sub>B<\/jats:sub> between 0.15 and 0.35). Addition of equimolar ethanol yields higher resolution than isopropanol, <jats:italic>R<\/jats:italic><jats:sub>S<\/jats:sub> values ranging between 1.54 and 2.75, whereas the latter allows to achieve moderately increased enatioselectivity. The resolution was further improved by using a ternary mixture of <jats:italic>n<\/jats:italic>\u2010hexane:methanol:isopropanol\/85:5:10 (v\/v). The most pronounced selectivity factor \u03b1 and resolution <jats:italic>R<\/jats:italic><jats:sub>S<\/jats:sub> values were obtained for the <jats:italic>para<\/jats:italic>\u2010hydroxy substituted compound, indicating that chiral recognition is sensitive to steric and stereoelectronic factors. In the course of optimization, the temperature\u2010dependence on the chiral separation was also investigated. It turned out that the enantiomer separation is predominantly enthalpically driven in normal phase mode. Chirality, 2009. \u00a9 2008 Wiley\u2010Liss, Inc.<\/jats:p>","DOI":"10.1002\/chir.20640","type":"journal-article","created":{"date-parts":[[2008,8,12]],"date-time":"2008-08-12T20:33:18Z","timestamp":1218573198000},"page":"199-207","source":"Crossref","is-referenced-by-count":17,"title":["Enantiomer separation of imidazo\u2010quinazoline\u2010dione derivatives on quinine carbamate\u2010based chiral stationary phase in normal phase mode"],"prefix":"10.1002","volume":"21","author":[{"given":"Krisztina","family":"Gyimesi\u2010Forr\u00e1s","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Norbert M.","family":"Maier","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"J\u00f3zsef","family":"K\u00f6k\u00f6si","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andr\u00e1s","family":"Gergely","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Wolfgang","family":"Lindner","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2008,8,12]]},"reference":[{"key":"e_1_2_1_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/0021-9673(96)00137-9"},{"key":"e_1_2_1_3_2","unstructured":"LindnerW L\u00e4mmerhoferM MaierNM. 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