{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2024,6,6]],"date-time":"2024-06-06T05:54:08Z","timestamp":1717653248441},"reference-count":19,"publisher":"Wiley","issue":"8","license":[{"start":{"date-parts":[[2008,11,20]],"date-time":"2008-11-20T00:00:00Z","timestamp":1227139200000},"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":[[2009,8]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>To obtain milligram amounts of the enantiomers of benzoxazolinone derivatives to be tested for binding to adrenergic sites, analytical HPLC methods using derivatized amylose chiral stationary phases were developed for the direct enantioseparation of benzoxazolinone aminoalcohols and their aminoketone precursors, derivatives with one or two chirals centers. The separations were made using normal phase methodology with a mobile phase of <jats:italic>n<\/jats:italic>\u2010hexane\u2010alcohol (ethanol, 1\u2010propanol, or 2\u2010propanol) in various proportions, and silica\u2010based amylose (tris\u20103, 5\u2010dimethylphenylcarbamate) Chiralpak AD and (tris\u2010(<jats:italic>S<\/jats:italic>)\u20101\u2010phenylethylcarbamate) Chiralpak AS columns. The effects of concentration of various aliphatic alcohols in the mobile phase were studied. The best separation was achieved on Chiralpak AS, so preparative HPLC was set up with this chiral stationary phase using a mobile phase consisting of <jats:italic>n<\/jats:italic>\u2010hexane\u2010alcohol using isocratic conditions and multiple repetitive injections. Physicochemicals properties of enantiomers were reported The effect of structural features of the solutes on discrimination between the enantiomers was examined. Limit of detection (LD) and limit of quantification (LQ) were determined using both ultra\u2010violet (UV) and evaporative light\u2010scattering detection (ELSD). Chirality, 2009. \u00a9 2008 Wiley\u2010Liss, Inc.<\/jats:p>","DOI":"10.1002\/chir.20678","type":"journal-article","created":{"date-parts":[[2008,11,20]],"date-time":"2008-11-20T19:49:25Z","timestamp":1227210565000},"page":"769-776","source":"Crossref","is-referenced-by-count":8,"title":["Enantioseparation of benzoxazolinone aminoalcohols and their aminoketone precursors, potential adrenergic ligands, by analytical and preparative liquid chromatography on amylose chiral stationary phases and characterization of the enantiomers"],"prefix":"10.1002","volume":"21","author":[{"given":"Emmanuelle","family":"Lipka","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Claude","family":"Vaccher","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jean\u2010Paul","family":"Bonte","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2008,11,20]]},"reference":[{"key":"e_1_2_1_2_2","first-page":"257","article-title":"Benzoxazolinone phenylethanolamine antagonists of adrenergic receptors. A chemical and pharmacodynamic study","volume":"41","author":"Vaccher MP","year":"1986","journal-title":"Il Farmaco"},{"key":"e_1_2_1_3_2","first-page":"854","article-title":"Synthesis and pharmacologic study of 6\u2010(amino\u20102 ethyl) benzoxazolinones","volume":"40","author":"Caignard DH","year":"1985","journal-title":"Il Farmaco"},{"key":"e_1_2_1_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/0223-5234(90)90120-R"},{"key":"e_1_2_1_5_2","unstructured":"PATENTANSPR\u00dcCHE WO\/2007\/104772 A1 \u201c Neue enantiomerenreine \u03b2\u2010agonisten verfahren zu deren herstellung und deren verwendung als arzneimittel.\u201d"},{"key":"e_1_2_1_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2004.05.008"},{"key":"e_1_2_1_7_2","unstructured":"Instruction Manual for Chiralpak AS and Instruction Manual for Chiralpak AD Daicel Chemical Industries Baker France March2003."},{"key":"e_1_2_1_8_2","first-page":"477","volume-title":"Chiral separations by HPLC","author":"Shibukawa A","year":"1989"},{"key":"e_1_2_1_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/0021-9673(94)00789-C"},{"key":"e_1_2_1_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/0021-9673(94)80400-1"},{"key":"e_1_2_1_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/chir.530060412"},{"key":"e_1_2_1_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19980504)37:8<1020::AID-ANIE1020>3.0.CO;2-5"},{"key":"e_1_2_1_13_2","unstructured":"GuiochonG ShiraziSG KattiAM.Fundamentals of preparative and nonlinear chromatography. 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