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(E)-2-Benzylidenebenzocyclanones, part VIII: spectrophotometric determination of pK a values of some natural and synthetic chalcones and their cyclic analogues

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Abstract

UV–Vis spectrophotometry was used to determine acid dissociation constant (pK a) values of the natural flavonoids phloretin, phlorizin, naringenin, and naringin, as well as 4′-hydroxychalcone, 4′-(dimethylamino)chalcone, and their cyclic analogues. Comparison of the results with those previously reported for the natural flavonoids showed the applied method is a relatively straightforward and easy-to-perform technique for the determination of pK a values of compounds with relatively low solubility. Comparative analysis of the pK a values of the synthetic chalcones showed a strong correlation between the degree of conjugation and the acid strength of the respective compounds with different geometry. Our results provide further evidence that modification of the three-dimensional structure of open-chain bioactive compounds is the method of choice to modify not only their stereochemistry but also their physicochemical properties.

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Acknowledgments

We are grateful to Zsuzsanna Moravecz (University of Pécs) for her excellent technical assistance and to the Slovak Grant Agency for Science (VEGA 1/2267/05) and Faculty of Medicine Research Fund (AOK-KA 34039-12/2009), University of Pécs for financial support.

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Authors and Affiliations

  1. Faculty of Medicine, Institute of Medical Chemistry, Biochemistry, Clinical Biochemistry and Labmed, a.s., University of PJ Šafárik, Košice, Slovakia

    Ivan Kron, Beáta Veliká & Juraj Guzy

  2. Faculty of Medicine, Institute of Medical Chemistry, Biochemistry and Clinical Biochemistry, Comenius University, Bratislava, Slovakia

    Zuzana Pudychová-Chovanová

  3. Institute of Pharmaceutical Chemistry, University of Pécs, Pécs, Hungary

    Pál Perjési

Authors
  1. Ivan Kron
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  2. Zuzana Pudychová-Chovanová
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  3. Beáta Veliká
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  4. Juraj Guzy
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  5. Pál Perjési
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Corresponding author

Correspondence to Ivan Kron.

Additional information

For part VII, see [1].

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Kron, I., Pudychová-Chovanová, Z., Veliká, B. et al. (E)-2-Benzylidenebenzocyclanones, part VIII: spectrophotometric determination of pK a values of some natural and synthetic chalcones and their cyclic analogues. Monatsh Chem 143, 13–17 (2012). https://doi.org/10.1007/s00706-011-0633-0

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  • DOI: https://doi.org/10.1007/s00706-011-0633-0

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