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@article{553682,
author = {Navrátilová, Hana and Opatřilová, Radka and Kříž, Zdeněk and Koča, Jaroslav},
article_number = {3},
keywords = {aryloxyaminopropanols; enantioselective HPLC; Chiralcel OD-H; Chiralpak AD; chiral recognition; low-energy conformers; molecular modeling},
language = {eng},
issn = {0899-0042},
journal = {Chirality},
title = {Enantioselective chromatography and molecular modeling of novel aryloxyaminopropan-2-ols with the alkyl carbamate function.},
volume = {16},
year = {2004}
}
TY - JOUR
ID - 553682
AU - Navrátilová, Hana - Opatřilová, Radka - Kříž, Zdeněk - Koča, Jaroslav
PY - 2004
TI - Enantioselective chromatography and molecular modeling of novel aryloxyaminopropan-2-ols with the alkyl carbamate function.
JF - Chirality
VL - 16
IS - 3
SP - 139-146
EP - 139-146
SN - 08990042
KW - aryloxyaminopropanols
KW - enantioselective HPLC
KW - Chiralcel OD-H
KW - Chiralpak AD
KW - chiral recognition
KW - low-energy conformers
KW - molecular modeling
N2 - A series of different racemic aryloxyaminopropan-2-ol derivatives 1a-d-3a-d with potential -adrenergic blocking effects related to propanolol 4 and atenolol 5 was resolved by HPLC using Chiralcel OD-H and Chiralpak AD as chiral stationary phases. Mobile phases consisted of a hexane/alcohol (propan-2-ol or ethanol) mixture doped with a modifier (DEA or TFA). The retention behavior of the compounds depended on the position of the carbamate attached to the aryloxy moiety and on the length of the alkyl residue in the carbamate. Enantiomers of the title compounds were baseline separated with the separation factors and resolutions Rs varying in the range of 1.34-4.55 and 1.50-10.65, respectively. The chromatographic systems developed can be used for the determination of the enantiomeric purity of the title compounds. Molecular modelling using empirical molecular mechanics and ab initio quantum chemistry methods provided low-energy structures in which sites of potential interactions responsible for retention behavior and chiral recognition could be identified
ER -
NAVRÁTILOVÁ, Hana, Radka OPATŘILOVÁ, Zdeněk KŘÍŽ a Jaroslav KOČA. Enantioselective chromatography and molecular modeling of novel aryloxyaminopropan-2-ols with the alkyl carbamate function. \textit{Chirality}. roč.~16, č.~3, s.~139-146. ISSN~0899-0042. 2004.
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