Enantiomers of C(5)-chiral 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives: Analytical and semipreparative HPLC separation, chiroptical properties, absolute configuration, and inhibitory activity against monoamine oxidase

Chirality
Roberto CirilliFrancesco La Torre

Abstract

The HPLC enantiomer separation of a novel series of C(5)-chiral 1-acetyl-3-(4-hydroxy- and 2,4-dihydroxyphenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole derivatives, with inhibitory activity against monoamine oxidases (MAO) type A and B, was accomplished using polysaccharide-based chiral stationary phases (CSPs: Chiralpak AD, Chiralcel OD, and Chiralcel OJ). Pure alcohols, such as ethanol and 2-propanol, and typical normal-phase binary mixtures, such as n-hexane and alcohol modifier, were used as mobile phases. Single enantiomers of several analytes examined were isolated on a semipreparative scale, and their chiroptical properties were measured. The assignment of the absolute configuration was established for one compound by single-crystal X-ray diffraction method and for the other three by CD spectroscopy. The inhibitory activity against MAO of racemic samples and single enantiomers were evaluated in vitro.

References

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Citations

Oct 9, 2013·European Journal of Medicinal Chemistry·B Vishnu NayakVenkatesan Jayaprakash
Apr 13, 2012·Organic & Biomolecular Chemistry·Olivier MahéJean-François Brière
Jun 18, 2011·Bioorganic & Medicinal Chemistry Letters·Monika JagratVenkatesan Jayaprakash
Sep 10, 2008·Chirality·Roberto CirilliAntonello Mai
Jun 20, 2008·Journal of Separation Science·Roberto CirilliFrancesco La Torre
Oct 1, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Robert P SheridanChristopher J Welch

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