Structure-activity relationships of antileishmanial and antimalarial chalcones


Liu, M; Wilairat, P; Croft, SL; Tan, AL; Go, ML; (2003) Structure-activity relationships of antileishmanial and antimalarial chalcones. Bioorganic & medicinal chemistry, 11 (13). pp. 2729-38. ISSN 0968-0896 DOI: https://doi.org/10.1016/s0968-0896(03)0233-5

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Abstract

A series of oxygenated chalcones which have been evaluated earlier for antimalarial activity (Plasmodium falciparum K1) were tested for antileishmanial activity against Leishmania donovani amastigotes. A comparison of structure-activity relationships reveal that different physicochemical and structural requirements exist for these two activities. Antileishmanial activity is associated with less lipophilic chalcones, in particular those with 4'-hydroxyl-substituted B rings and hetero/polyaromatic A rings. In contrast, chalcones with good antimalarial activity have alkoxylated B rings and electron-deficient A rings. Visualization of the steric and electrostatic fields generated from comparative molecular field analysis (CoMFA) indicate that the ring A of chalcones make a more significant contribution to antileishmanial activity while both rings A and B are important for antimalarial activity. Despite different requirements, two alkoxylated chalcones (8, 19) were identified which combined good antimalarial and antileishmanial activities.

Item Type: Article
Faculty and Department: Faculty of Infectious and Tropical Diseases > Dept of Immunology and Infection
Research Centre: Leishmaniasis Group
Neglected Tropical Diseases Network
PubMed ID: 12788347
Web of Science ID: 183590100008
URI: http://researchonline.lshtm.ac.uk/id/eprint/15628

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