Mei LiuPrapon WilairatSimon L. CroftAgnes Lay Choo TanMei Lin GoNational University of SingaporeMahidol UniversityLondon School of Hygiene & Tropical Medicine2018-07-242018-07-242003-07-03Bioorganic and Medicinal Chemistry. Vol.11, No.13 (2003), 2729-2738096808962-s2.0-0038548308https://repository.li.mahidol.ac.th/handle/20.500.14594/20712A 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.Mahidol UniversityBiochemistry, Genetics and Molecular BiologyChemistryPharmacology, Toxicology and PharmaceuticsArticleSCOPUS10.1016/S0968-0896(03)00233-5