NMR determination of pKa values of indoloquinoline alkaloids
| Authors | |
|---|---|
| Year of publication | 2009 |
| Type | Article in Periodical |
| Magazine / Source | Magnetic Resonance in Chemistry |
| MU Faculty or unit | |
| Citation | |
| 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 |
| Attached files | |
| 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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