Publication: Structure-activity relationships of antileishmanial and antimalarial chalcones
Issued Date
2003-07-03
Resource Type
ISSN
09680896
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2-s2.0-0038548308
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Mahidol University
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SCOPUS
Bibliographic Citation
Bioorganic and Medicinal Chemistry. Vol.11, No.13 (2003), 2729-2738
Suggested Citation
Mei Liu, Prapon Wilairat, Simon L. Croft, Agnes Lay Choo Tan, Mei Lin Go Structure-activity relationships of antileishmanial and antimalarial chalcones. Bioorganic and Medicinal Chemistry. Vol.11, No.13 (2003), 2729-2738. doi:10.1016/S0968-0896(03)00233-5 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/20712
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Title
Structure-activity relationships of antileishmanial and antimalarial chalcones
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.