Development and validation of a nonaqueous capillary electrophoretic method for the enantiomeric purity determination of a synthetic intermediate of new R/S-3,4-dihydro-2,2-dimethyl-2H-1-benzopyrans using a single-isomer anionic cyclodextrin derivative and an ionic liquid

Poster (2010, March)

Development and validation of a nonaqueous capillary electrophoretic method for the enantiomeric purity determination of a synthetic intermediate of new 3,4-dihydro-2,2-dimethyl-2H-1-benzopyrans using a single-isomer anionic cyclodextrin derivative and an ionic liquid

in Journal of Chromatography. A (2010)

The enantiomeric purity determination of a synthetic intermediate of new 3,4-dihydro-2,2-dimethyl-2H-1-benzopyrans, i.e. 4-amino-2,2-dimethyl-6-ethoxycarbonylamino-3,4-dihydro-2H-1-benzopyran, was ... [more ▼]

The enantiomeric purity determination of a synthetic intermediate of new 3,4-dihydro-2,2-dimethyl-2H-1-benzopyrans, i.e. 4-amino-2,2-dimethyl-6-ethoxycarbonylamino-3,4-dihydro-2H-1-benzopyran, was successfully carried out using an anionic cyclodextrin (CD) derivative combined with a chiral ionic liquid (IL). In order to obtain high resolution and efficiency values, the addition of a chiral IL, i.e. ethylcholine bis(trifluoromethylsulfonyl)imide (EtChol NTf2), to the background electrolyte containing heptakis(2,3-di-O-methyl-6-O-sulfo)-β-CD (HDMS-β-CD) was found to be essential. A simultaneous increase in separation selectivity and enantioresolution seems to indicate a synergistic effect of HDMS-β-CD and EtChol NTf2. The best enantioseparation of the key intermediate was achieved using a methanolic solution of 0.75 M formic acid, 10 mM ammonium formate, 1.5 mM HDMS-β-CD and 5 mM EtChol NTf2. Levamisole was selected as internal standard. The optimized conditions allowed the determination of 0.1 % of each enantiomer in the presence of its stereoisomer using the method of standard additions. The NACE method was then fully validated with respect to selectivity, response function, trueness, precision, accuracy, linearity and limits of detection and quantification. [less ▲]

Original cromakalim analogues as KATP channel openers

in Metabolic and Functional Research on Diabetes (2009), 2

new R/S-3,4-dihydro-2,2-dimethyl-6-halo-4-(phenylainothiocarbonylamino)-2H-1-benzopyrans structually related to (+/-)-cromakalim as tissue-selective pancreatic beta-celle KATP channel openers

in Bioorganic & Medicinal Chemistry (2008), 16

Design, Synthesis and Pharmacological Evaluation of R/S-3,4-Dihydro-2,2-Dimethyl-6-Halo-4-(Phenylaminocarbonylamino)-2H-1-Benzopyrans: Towards Tissue-Selective Pancreatic Beta-Cells KATP Channel Openers Structually Related to (+/-)-Cromakalim

in Journal of Medicinal Chemistry (2006), 49