(E)-2-Benzylidenebenzocyclanones, part VIII: spectrophotometric determination of pKa values of some natural and synthetic chalcones and their cyclic analogues |
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| Authors: | Ivan Kron Zuzana Pudychová-Chovanová Beáta Veliká Juraj Guzy Pál Perjési |
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| Affiliation: | (1) Faculty of Medicine, Institute of Medical Chemistry, Biochemistry, Clinical Biochemistry and Labmed, a.s., University of PJ Šaf?rik, Košice, Slovakia;(2) Faculty of Medicine, Institute of Medical Chemistry, Biochemistry and Clinical Biochemistry, Comenius University, Bratislava, Slovakia;(3) Institute of Pharmaceutical Chemistry, University of P?cs, P?cs, Hungary |
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| Abstract: | 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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