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|Title:||Structure-activity relationships of antileishmanial and antimalarial chalcones|
Simon L. Croft
Agnes Lay Choo Tan
Mei Lin Go
National University of Singapore
London School of Hygiene & Tropical Medicine
|Keywords:||Biochemistry, Genetics and Molecular Biology;Chemistry;Pharmacology, Toxicology and Pharmaceutics|
|Citation:||Bioorganic and Medicinal Chemistry. Vol.11, No.13 (2003), 2729-2738|
|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. © 2003 Elsevier Science Ltd. All rights reserved.|
|Appears in Collections:||Scopus 2001-2005|
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