Design and synthesis of naphthalene‐based chiral strong cation exchangers and their application for chiral separation of basic drugs

Abstract

In continuation of our efforts to synthesize a highly dedicated strong cation exchanger, we introduce four chiral stationary phases based on a laterally substituted naphthalene core featuring chiral 2-aminocyclohexansulfonic acid as the chiral cation-exchange site. The selectors were modified with two different terminal units, which enabled immobilization to the silica support by thiolene radical reaction or azide-yne click chemistry. The chromatographic parameters of these chiral stationary phases were determined using a set of chiral amines, mainly from the family of β-blocker pharmaceuticals. The chiral stationary phases immobilized by means of click chemistry were found to be superior to those possessing the sulfide linker to the silica support. The chromatographic results and visualization of density functional theory-calculated conformations of the selectors hint at a combination of a steric and electronic effect of the triazole ring in the course of chiral resolution of the target analytes.

A structural spectroscopic study of dissociative anaesthetic methoxphenidine

“…S1). The reversal of elution order can be achieved in several ways, typically by changing the CPS for its enantiomeric variant (for brush-type CSPs), 52 or via utilizing structurally modified selectors. 53 However, a change in chromatographic conditions can be sufficient to trigger the EEO as well.…”

4-Isobutylmethcathinone—A Novel Synthetic Cathinone with High In Vitro Cytotoxicity and Strong Receptor Binding Preference of Enantiomers

“…The following supporting information can be downloaded at: https: //www.mdpi.com/article/10.3390/ph15121495/s1, Scheme S1: General scheme of synthesis of 4-isobutylmethcathinone (4) and its formal metabolite; Figure S1: Mass spectrum of compound 4; Figure S2: Mass spectrum of compound 5; Figure S3: Mass spectrum of compound 6; Figure S4: HPLC chromatograms of IBMCat in heptane (red) and hexane (green) mobile phases measured on Amylose-SA column, and heptane (blue) and hexane (orange) mobile phases measured on Amylose-C column; Figure S5: Chromatograms of IBMCat in heptane (red) and hexane (green) mobile phases measured on Amylose-SA; Figure S6: Chromatograms of IBMCat in heptane (purple) and hexane (grey) mobile phases with ethanol as polar modifier measured on column Amylose-SA; Figure S7 S1: Retention times and calculated chromatographic parameters of IBMCat for each mobile phase employed on columns Amylose-SA (red and green) and Amylose-C (blue and orange); Table S2: Retention times and calculated analytical parameters of IBMCat for mobile phases containing either propan-2-ol or ethanol as modifier; column-Amylose-SA; Table S3: Plasmid DNA and its source used in PRESTO-Tango β-arrestin recruitment assay. References [28,[46][47][48][49][50] are cited in the Supplemmtary Materials.…”