Quantitative Structure-Activity Relationships of the Antimalarial Agent Artemisinin and Some of its Derivatives – A DFT Approach

Author(s): Sanchaita Rajkhowa, Iftikar Hussain, Kalyan K. Hazarika, Pubalee Sarmah, Ramesh Chandra Deka.

Journal Name: Combinatorial Chemistry & High Throughput Screening
Accelerated Technologies for Biotechnology, Bioassays, Medicinal Chemistry and Natural Products Research

Volume 16 , Issue 8 , 2013

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Artemisinin form the most important class of antimalarial agents currently available, and is a unique sesquiterpene peroxide occurring as a constituent of Artemisia annua. Artemisinin is effectively used in the treatment of drug-resistant Plasmodium falciparum and because of its rapid clearance of cerebral malaria, many clinically useful semisynthetic drugs for severe and complicated malaria have been developed. However, one of the major disadvantages of using artemisinins is their poor solubility either in oil or water and therefore, in order to overcome this difficulty many derivatives of artemisinin were prepared. A comparative study on the chemical reactivity of artemisinin and some of its derivatives is performed using density functional theory (DFT) calculations. DFT based global and local reactivity descriptors, such as hardness, chemical potential, electrophilicity index, Fukui function, and local philicity calculated at the optimized geometries are used to investigate the usefulness of these descriptors for understanding the reactive nature and reactive sites of the molecules. Multiple regression analysis is applied to build up a quantitative structure-activity relationship (QSAR) model based on the DFT based descriptors against the chloroquine-resistant, mefloquine-sensitive Plasmodium falciparum W-2 clone.

Keywords: Artemisinin, DFT, electrophilicity index (ω), Fukui function (FF), hardness (η), QSAR.

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Article Details

Year: 2013
Page: [590 - 602]
Pages: 13
DOI: 10.2174/1386207311316080002
Price: $65

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