Enantiomeric-Enriched Ferrocenes: Synthesis, Chiral Resolution, and Mathematic Evaluation of CD-chiral Selector Energies with Ferrocene-Conjugates

Snegur, L. V.; Borisov, Yurii A.; Kuzmenko, Yuliya V.; Davankov, V. A.; Ilyin, M. M.; Arhipov, Dmitry; Korlyukov, Аlexander А.; Kiselev, S. S.; Simenel, А. А.

doi:10.3390/molecules22091410

Cited by 6 publications

(7 citation statements)

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“…Early, we applied the DFT calculations to study the interactions of ferrocene azoles with CDs in the separation of ferrocene containing enantiomers by HPLC; CDs were used as chiral selectors [25]. Such inclusion complexes are well known for uncharged alpha‐, beta‐CD, and gamma‐CD [22].…”

Section: Resultsmentioning

confidence: 99%

“…( R , S )‐Ferrocenyl(ethyl)imidazole ( 1 ) was prepared from 1‐ferrocenylethanol and CDI under neutral conditions [41]. The synthesis of ferrocenyl(alkyl)azoles ( 2 – 6 ) in racemic forms and ( S )‐ 2 in enantio‐enriched form was carried out in the described manner under acidic conditions [25,26,42].…”

Section: Methodsmentioning

confidence: 99%

“…(S)‐N‐(ferrocenylethyl)pyrazole, (S)‐ 2 [25]: Orange crystals, yield 86%, m.p. 54°C, ee 95% (HPLC), [α] D 20 +16.50 ( c , 0.7; in benzene) IR (KBr) ν , cm −1 : 3115, 2965, 1525, 1411, 1293, 1120, 1045, 968, 853, 720, 665, 538, 498.…”

Section: Methodsmentioning

confidence: 99%

“…Our scientific interests are associated with the biological active ferrocene compounds usually containing a chiral carbon atom in the alpha‐position to the cyclopentadienyl ring (Fig. 1); therefore, the above compounds usually present racemic mixtures of two enantiomers [22–26]. In accordance with pharmacopeias of European countries, investigation of biological effects of each of the two stereoisomers of potential drugs is needed [27,28].…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, analytical separation of ferrocene mixtures of enantiomers was successfully carried out by HPLC [22–26,36]. Quantum chemical (QC) calculations in this area were performed by the density functional theory (DFT) in parallel with enantiomeric resolution of bioactive ferrocene pyrazoles using chiral HPLC and a high correlation between experimental HPLC data and calculated interaction energies values was obtained [25]. Although the pharmacological aspects of the use of CE were well represented in the reviews [37,38], by the time our studies began, no publications describing CE techniques for analytical resolution of racemic organometallic ferrocene compounds had been available.…”

Section: Introductionmentioning

confidence: 99%

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Application of capillary electrophoresis technique for the enantioseparation of bioactive ferrocene‐based compounds versus DFT calculated data

et al. 2020

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Herein, a series of bioactive ferrocene‐modified N‐heterocycles with alkyl linkers was prepared in good to quantitative yields starting from easy accessible ferrocene alcohols and heterocycles under acidic or neutral (for imidazole) conditions in racemic forms. The analytical resolution of a number of bioactive racemic ferrocene azoles 1–6 (where azole = imidazole, pyrazole, and benzotriazole derivatives) into enantiomers was first carried out by CE using sulfobuthylether‐β‐CD (captisol) as a chiral selector. The analytical approaches to highly enantiomeric‐enriched ferrocene derivatives are based on the formation of their inclusion complexes. The best chiral separation was achieved using zone CE in a quartz capillary. The ACE was used to evaluate the stability constants of captisol complexes with enantiomeric forms of two ferrocene derivatives 1, FcCHMe‐imidazole, and 6, FcCHMe‐benzotriazole. The optimal conditions for the resolution of the studied (R, S)‐ferrocene compounds 1, 2, and 6 were predicted on the basis of the performed quantum chemical calculations and then implemented by the electrophoretic method. A high correlation between density functional theory calculation results and experimental electrophoresis data were obtained. Successful enantioseparation of racemic mixtures is of great importance for the characterization and further applications of drug candidates in enantiopure forms and in the development of clinical treatment. The advantages of the CE procedure make it possible to have important practical value and significance for determining the purity and enantiomeric excess of other ferrocene‐containing compounds.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%