Title
NMR determination of <tex>$pK_{a}$</tex> values of indoloquinoline alkaloids NMR determination of <tex>$pK_{a}$</tex> values of indoloquinoline alkaloids
Author
Faculty/Department
Faculty of Sciences. Chemistry
Faculty of Pharmaceutical, Biomedical and Veterinary Sciences. Pharmacy
Publication type
article
Publication
Chichester ,
Subject
Physics
Chemistry
Source (journal)
Magnetic resonance in chemistry. - Chichester
Volume/pages
47(2009) :11 , p. 977-981
ISSN
0749-1581
ISI
000271123300010
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
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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