Probing (13)C chemical shielding tensors in cryptolepine and two bromo-substituted analogs for antiplasmodial activity
2011 (English)In: Journal of Molecular Modeling, ISSN 1610-2940, E-ISSN 0948-5023, Vol. 17, no 12, 3289-3297 p.Article in journal (Refereed) Published
Density functional theory calculations were applied to investigate (13)C chemical shielding tensors in cryptolepine and its bromo-substituted analogs, 2-bromocryptolepine and 2,7-dibromocryptolepine. The fact that bromo-substituted cryptolepine shows higher antiplasmodial activity than cryptolepine raises the question of whether this effect can be related to the electronic properties around carbon atoms. The results show that changes to the principal components of the shielding tensors upon substitution are significant. In particular, sigma (33) is the most affected tensor for carbons in the substituted ring, which could be related to the increased antiplasmodial activity of bromosubstituted cryptolepine. The analyses were also focused on atomic charges and dipole moment.
Place, publisher, year, edition, pages
2011. Vol. 17, no 12, 3289-3297 p.
Cryptolepine, Malaria, Density functional theory, Chemical shielding, Antiplasmodial activity
IdentifiersURN: urn:nbn:se:uu:diva-165643DOI: 10.1007/s00894-011-1009-4ISI: 000297548000024OAI: oai:DiVA.org:uu-165643DiVA: diva2:474416