| Synthesis and chromatographic enantioresolution of anti-HIV quinolone derivatives. | |
| | |
MedLine Citation:
|
PMID: 21807200 Owner: NLM Status: In-Data-Review |
Abstract/OtherAbstract:
|
The successful enantioseparation of five 6-desfluoroquinolones with three polysaccharide-based stationary phases (namely, the cellulose-based Chiralpak IB and the two amylose-based Chiralpak AD-H and Lux Amylose-2) is herein described. The investigated species differ for the nature of substituents and/or the position of the stereogenic centre on the quinolone scaffold. The effect on the enantioseparation performance exerted by the different morphology of the cellulose-based and amylose-based polymers, was systematically evaluated for all compounds. In this frame, the impact of alternative alcoholic (ethanol, 2-ethoxyethanol, methanol, 2-propanol) and acidic (acetic, methanesulfonic and trifluoroacetic acid) modifiers as well as of a "non-standard" solvent (chloroform), was investigated in normal phase conditions along with the stereo-electronic peculiarities of the selected polymers. While 7-[4-(1,3-benzothiazol-2-yl)-2-methyl-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid (1) was enantioresolved with conventional normal-phase conditions by means of the largely employed amylose-based Chiralpak AD-H column, the recruitment of a bulky alcohol (2-ethoxyethanol) succeeded in the enantioresolution of 6-amino-1-methyl-7-[2-methyl-4-(2-pyridinyl)-1-piperazinyl]-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid (2) and 6-amino-1-[1-(hydroxymethyl)propyl]-4-oxo-7-(4-pyridin-2-ylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid (3) with the same column. The use of the amylose-based Lux Amylose-2 column, carrying both an electro-withdrawing (chlorine) and an electro-donating (methyl) group on the carbamate residue, allowed to get 6-amino-1-methyl-4-oxo-7-[3-(2-pyridinyl)-1-pyrrolidinyl]-1,4-dihydro-3-quinolinecarboxylic acid hydrochloride (4) enanantioresolved, and 6-amino-1-methyl-4-oxo-7-(3-pyridin-2-ylpiperidin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid (5) enantioseparated. |
| | |
Authors:
|
Benedetto Natalini; Roccaldo Sardella; Serena Massari; Federica Ianni; Oriana Tabarrini; Violetta Cecchetti |
Publication Detail:
|
Type: Journal Article Date: 2011-06-22 |
Journal Detail:
|
Title: Talanta Volume: 85 ISSN: 1873-3573 ISO Abbreviation: Talanta Publication Date: 2011 Sep |
Date Detail:
|
Created Date: 2011-08-02 Completed Date: - Revised Date: - |
Medline Journal Info:
|
Nlm Unique ID: 2984816R Medline TA: Talanta Country: England |
Other Details:
|
Languages: eng Pagination: 1392-7 Citation Subset: IM |
Copyright Information:
|
Copyright © 2011 Elsevier B.V. All rights reserved. |
Affiliation:
|
Dipartimento di Chimica e Tecnologia del Farmaco, Università degli Studi di Perugia, Via del Liceo 1, 06123 Perugia, Italy. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
|
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Pink shrimp (P. brasiliensis and P. paulensis) residue: Influence of extraction method on carotenoid...
Next Document: Polarographic study of hydrogen peroxide anodic current and its application to antioxidant activity ...