2-Phenylaminonaphthoquinones and related compounds: Synthesis,trypanocidal and cytotoxic activities |
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| Affiliation: | 1. Departamento de Química Orgánica, Facultad de Química, Pontificia Universidad Católica de Chile, 702843 Santiago de Chile, Chile;2. Centro Singular de Investigación en Química Biológica y Materiales Moleculares and Departamento de Química Orgánica (Facultad de Química), Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain;3. Facultad de Farmacia, Universidad de Valparaíso, Av. Gran Bretaña N 1093, Valparaíso, Chile;4. Centro de Investigaciones Biomédicas, Escuela de Medicina, Universidad de Valparaíso, Av. Hontaneda N° 2664, Valparaíso, Chile;5. Instituto de Ciencias Biomédicas, Programa de Farmacología Molecular y Clínica, Universidad de Chile, PO Box 70000, Santiago, Chile;6. Departamento de Química, Facultad de Ciencias, Universidad de Chile, PO Box 653, Santiago, Chile;1. Department of Chemistry, University of Pune, Pune 411007, India;2. MPI für Chemische Energiekonversion, Stiftstr. 34-36, 45470 Müllheim an der Ruhr, Germany;3. Center for Material Characterization, National Chemical Laboratory, Pune 411008, India;4. School of Biological Sciences, National Institute of Science Education and Research (NISER), Bhubaneswar 751005, India;1. Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai, Tamil Nadu 625 021, India;2. Institute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia;3. New Drug Discovery Research, Department of Medicinal Chemistry, Sunrise University, Alwar, Rajasthan 301030, India;1. Centre for Chemical Biology, Chemistry, School of Environmental and Life Sciences, The University of Newcastle, Callaghan, NSW 2308, Australia;2. Children''s Medical Research Institute, University of Sydney, Westmead, NSW 2145, Australia;3. Department of Medicinal Chemistry, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt;1. School of Biological Sciences, National Institute of Science Education and Research (NISER), Bhubaneswar 751 005, India;2. Department of Chemistry, University of Pune, Pune 411 007, India;3. MPI für Chemische Energiekonversion, Stiftstr. 34-36, 45470 Müllheim an der Ruhr, Germany;4. Inorganic and Physical Chemistry Department, Indian Institute of Science, Bangalore, India;1. Facultad de Ciencias Químicas, Universidad Autónoma de San Luis Potosí, Manuel Nava No. 6, 78210 San Luis Potosí, SLP, Mexico;2. Department of Chemistry, University of Western Ontario, London, ON, Canada N6A 5B7;3. Facultad de Ciencias Químicas, Universidad Autónoma de Coahuila, Blvd. V. Carranza e Ing. José Cárdenas s/n Col. República, C.P. 25250 Saltillo, COAH, Mexico |
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| Abstract: | A series of new 2-aminonaphthoquinones and related compounds were synthesized and evaluated in vitro as trypanocidal and cytotoxic agents. Some tested compounds inhibited epimastigote growth and trypomastigote viability. Several compounds showed similar or higher activity and selectivity as compared with current trypanocidal drug, nifurtimox. Compound 4l exhibit higher selectivity than nifurtimox against Trypanosoma cruzi in comparison with Vero cells. Some of the synthesized quinones were tested against cancer cells and normal fibroblasts, showing that certain chemical modifications on the naphthoquinone moiety induce and excellent increase the selectivity index of the cytotoxicity (4g and 10). The results presented here show that the anti-T. cruzi activity of 2-aminonaphthoquinones derivatives can be improved by the replacement of the benzene ring by a pyridine moiety. Interestingly, the presence of a chlorine atom at C-3 and a highly lipophilic alkyl group or aromatic ring are newly observed elements that should lead to the discovery of more selective cytotoxic and trypanocidal compounds. |
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| Keywords: | 2-Phenylaminonaphthoquinones Cytotoxicity Benzocarbazolequinones Electronic properties |
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