NMR determination of pKa values of indoloquinoline alkaloids


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Year of publication 2009
Type Article in Periodical
Magazine / Source Magnetic Resonance in Chemistry
MU Faculty or unit

Faculty of Science

Web DOI: 10.1002/mrc.2494
Doi http://dx.doi.org/10.1002/mrc.2494
Field Physical chemistry and theoretical chemistry
Keywords 1H NMR;chemical shift;cryptolepine;isocryptolepine;neocryptolepine;isoneocryptolepine;malaria;pH;determination of pKa
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Description Malaria is one of the most serious global health problems. Isolating new therapeutic agents with potential antimalarial activity from natural sources or preparing such agents either semisynthetically or synthetically is one strategy for solving the problem of resistance constantly evolving to the drugs currently in use. For alkaloids, the acid-base dissociation constant, pKa, is an important characteristic, thought to be associated with biological activity. In this contribution, pKa values for several indoloquinoline alkaloids were determined by using 1H NMR spectroscopy in a mixture of solvents. The data were recalculated for water solutions using the correction factors reported previously. The structural dependence of the pKa values for cryptolepine and its isomers neocryptolepine, isocryptolepine and isoneocryptolepine as well as some substituted neocryptolepine derivatives is discussed.
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