Synthesis of novel triazole-linked mefloquine derivatives: Biological evaluation against Plasmodium falciparum |
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| Affiliation: | 1. Department of Chemistry and Polymer Science, University of Stellenbosch, Private Bag X1, Matieland 7602, South Africa;2. Department of Pharmacology, University of Cape Town, Groote Schuur Hospital, South Africa;1. Department of Microbiology, Immunology, and Pathology, Colorado State University, Fort Collins, Colorado, 80523;2. School of Biosciences, College of Life and Environmental Sciences, University of Birmingham, Edgbaston, Birmingham, B15, United Kingdom;3. Center for Computational Science, University of Miami, Miami, Florida, 33136;4. Biomedical Informatics Center, National Institute for Research in Reproductive Health, Indian Council of Medical Research, Mumbai, India, 400012;6. Department of Pharmacology, Miller School of Medicine, University of Miami, Miami, Florida, 33136;8. Institute for Molecular Medicine Finland, University of Helsinki, Helsinki, Finland, 00100;9. Department of Chemistry, College of Arts and Sciences, University of Alabama at Birmingham, Birmingham, Alabama, 35205;1. Organic Chemistry Division-II (CPC Division), CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, Telangana, India;2. Medicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad 500078, Telangana, India;1. Global API Chemistry, Product Development, GlaxoSmithKline, Research Triangle Park, NC 27709, United States;2. 2nd Generation and Process Robustness, Product Development, GlaxoSmithKline, Currabinny, Carrigaline, County Cork, Ireland;1. Dipartimento di Scienze del Farmaco, Università degli Studi di Catania, V.le A. Doria, 95125, Catania, Italy;2. Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria, 6, 95125, Catania, Italy;3. CNR-IPCB Istituto per i Polimeri, Compositi e Biomateriali, Via P. Gaifami 18, I-95126, Catania, Italy;4. CNR-IPCF Istituto per i Processi Chimico-Fisici, Viale F. Stagno d’Alcontres 37, I-98158, Messina, Italy;5. INSTM Consorzio Interuniversitario Nazionale per la Scienza e Tecnologia dei Materiali (UdR of Catania), Viale A. Doria, 6, I-95125, Catania, Italy;6. Laboratory of Epithelial Biology, Department of Periodontics and Oral Medicine, University of Michigan School of Dentistry, Ann Arbor, MI, 48109-1078, USA |
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| Abstract: | Using 2,8-bis(trifluoromethyl)quinoline, the pharmacophore of mefloquine, as scaffold, eleven novel triazole-linked compounds have been synthesised by the application of CuAAC chemistry. The in vitro biological activity of the compounds on the Plasmodium falciparum chloroquine-sensitive strain NF54 was then determined. The compounds all showed IC50s in the lower μM range with (1R,3S,5R)-N-{[1-(2,8-bis(trifluoromethyl)quinoline-4-yl)-1H-1,2,3-triazol-4-yl]methyl}adamantan-2-amine (29) exhibiting the best activity of 1.00 μM. |
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| Keywords: | 2,8-Bis(trifluoromethyl)quinoline 1,2,3-Triazole CuAAC chemistry |
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