Antichagasic evaluation, molecular docking and ADMET properties of the chalcone (2E)-3-(2-fluorophenyl)-1-(2-hydroxy- 3,4,6-trimethoxyphenyl)prop-2-en-1-one against Trypanosoma cruzi

References

• Adade, C. M. (2010). Contributions of ultrastructural studies to the cell biology of trypanosmatids: Targets for anti-parasitic drugs. The Open Parasitology Journal, 4(1), 178–187. https://doi.org/10.2174/1874421401004010178
   Google Scholar
• Allouche, A. R. (2011). Gabedit—A graphical user interface for computational chemistry softwares. Journal of Computational Chemistry, 32(1), 174–182. https://doi.org/10.1002/jcc.21600
   PubMed Web of Science ®Google Scholar
• Almeida-Neto, F. W. Q., da Silva, L. P., Ferreira, M. K. A., Mendes, F. R. S., de Castro, K. K., Bandeira, P. N., de Menezes, J. E. S., dos Santos, H. S., Monteiro, N. K., Marinho, E. S., & de Lima-Neto, P. (2020). Characterization of the structural, spectroscopic, nonlinear optical, electronic properties and antioxidant activity of the N-{4’-[(E)-3-(Fluorophenyl)-1-(phenyl)-prop-2-en-1-one]}-acetamide. Journal of Molecular Structure, 1220, 128765. https://doi.org/10.1016/j.molstruc.2020.128765
   Web of Science ®Google Scholar
• Alves, D. F., Muniz, A., S., C., Abrel, C. D. R., Freitas, N. R., Teixeira, A. B., & Ferreira, E. S. (2018). Métodos de diagnóstico para a doença de Chagas: uma atualização. Revista brasileira de Analálise Clinica, 50(4), 330–333.
   Google Scholar
• Aponte, J. C., Verástegui, M., Málaga, E., Zimic, M., Quiliano, M., Vaisberg, A. J., Gilman, R. H., & Hammond, G. B. (2008). Synthesis, cytotoxicity, and anti-Trypanosoma cruzi activity of new chalcones. Journal of Medicinal Chemistry, 51(19), 6230–6234. https://doi.org/10.1021/jm800812k
   PubMed Web of Science ®Google Scholar
• Bandeira, P. N., Lemos, T. L. G., Santos, H. S., de Carvalho, M. C. S., Pinheiro, D. P., de Moraes Filho, M. O., Pessoa, C., Barros-Nepomuceno, F. W. A., Rodrigues, T. H. S., Ribeiro, P. R. V., Magalhães, H. S., & Teixeira, A. M. R. (2019). Synthesis, structural characterization, and cytotoxic evaluation of chalcone derivatives. Medicinal Chemistry Research, 28(11), 2037–2049. https://doi.org/10.1007/s00044-019-02434-1
   Web of Science ®Google Scholar
• Battista, T., Gianni, C., Andrea, I., & Annarita, F. (2020). Targeting trypanothione reductase, a key enzyme in the redox trypanosomatid metabolism, to develop new drugs against leishmaniasis and trypanosomiases. Molecules, 25(8), 1924–1917. https://doi.org/10.3390/molecules25081924
   PubMed Web of Science ®Google Scholar
• Becke, A. D. (1992). Density‐functional thermochemistry. I. The effect of the exchange‐only gradient correction. The Journal of Chemical Physics, 96(3), 2155–2160. https://doi.org/10.1063/1.462066
   Web of Science ®Google Scholar
• Belluti, F., Elisa, U., Giacomo, V., Christian, B., Marcel, K., Reto, B., Angelo, V., Romana, F., Paul, A. M., Michels, Luise, R. K. S., Andrea, C., & Maria, L. B. (2014). Toward the development of dual-targeted glyceraldehyde-3-phosphate dehydrogenase/trypanothione reductase inhibitors against Trypanosoma Brucei and Trypanosoma Cruzi. ChemMedChem,.9(2), 371–382. https://doi.org/10.1002/CMDC.201300399.
   PubMed Web of Science ®Google Scholar
• Bickerton, G. R., Paolini, G. V., Besnard, J., Muresan, S., & Hopkins, A. L. (2012). Quantifying the chemical beauty of drugs. Nature Chemistry, 4(2), 90–98. https://doi.org/10.1038/nchem.1243
   PubMed Web of Science ®Google Scholar
• Biovia, D. S., Berman, H. M., & Westbrook, J. (2000). Dassault Systemes BIOVIA, discovery studio visualizer. Journal of Chemical Physics, 17(2), 0021–0999.
   Google Scholar
• Böhm, H. J., David, B., Stefanie, B., Manfred, K., Bernd, K., Klaus, M., Ulrike, O., & Martin, S. (2004). Fluorine in medicinal chemistry. ChemBioChem, 5(5), 637–643. https://doi.org/10.1002/cbic.200301023
   PubMed Web of Science ®Google Scholar
• Borsari, C., Santarem, N., Torrado, J., Olías, A. I., Corral, M. J., Baptista, C., Gul, S., Wolf, M., Kuzikov, M., Ellinger, B., Witt, G., Gribbon, P., Reinshagen, J., Linciano, P., Tait, A., Costantino, L., Freitas-Junior, L. H., Moraes, C. B., Bruno Dos Santos, P., … Costi, M. P. (2017). Methoxylated 2'-hydroxychalcones as antiparasitic hit compounds. European Journal of Medicinal Chemistry, 126, 1129–1135. https://doi.org/10.1016/j.ejmech.2016.12.017
   PubMed Web of Science ®Google Scholar
• Braga, R. C., Alves, V. M., Silva, M. F. B., Muratov, E., Fourches, D., Lião, L. M., Tropsha, A., & Andrade, C. H. (2015). Pred‐hERG: A novel web‐accessible computational tool for predicting cardiac toxicity. Molecular Informatics, 34(10), 698–701. https://doi.org/10.1002/minf.201500040
   PubMed Web of Science ®Google Scholar
• Brak, K., Kerr, I. D., Barrett, K. T., Fuchi, N., Debnath, M., Ang, K., Engel, J. C., McKerrow, J. H., Doyle, P. S., Brinen, L. S., & Ellman, J. A. (2010). Nonpeptidic tetrafluorophenoxymethyl ketone cruzain inhibitors as promising new leads for Chagas disease chemotherapy. Journal of Medicinal Chemistry, 53(4), 1763–1773. https://doi.org/10.1021/jm901633v
   PubMed Web of Science ®Google Scholar
• Brenk, R., Schipani, A., James, D., Krasowski, A., Gilbert, I. H., Frearson, J., & Wyatt, P. G. (2008). Lessons learnt from assembling screening libraries for drug discovery for neglected diseases. ChemMedChem: Chemistry Enabling Drug Discovery, 3(3), 435–444. https://doi.org/10.1002/cmdc.200700139
   PubMed Web of Science ®Google Scholar
• Cheleski, J., Renato, F., Freitas, H. J. W., Josmar, R. R., Ana, P. U. A., & Carlos, A. M. (2011). Expression, purification and kinetic characterization of his-tagged glyceraldehyde-3-phosphate dehydrogenase from Trypanosoma Cruzi. Protein Expression and Purification, 76(2), 190–196. https://doi.org/10.1016/J.PEP.2010.11.013.
   PubMed Web of Science ®Google Scholar
• Coelho, G. S., Andrade, J. S., Xavier, V. F., Junior, P. A. S., Araujo, B. C. R., Fonseca, K. S., Caetano, M. S., Murta, S. M., Vieira, P. M., Carneiro, C. M., & Taylor, J. G. (2019). Design, synthesis, molecular modelling, and in vitro evaluation of tricyclic coumarins against Trypanosoma cruzi. Chemical Biology & Drug Design, 93(3), 337–350. ) https://doi.org/10.1111/cbdd.13420
   PubMed Web of Science ®Google Scholar
• Csizmadia, P. (1999). MarvinSketch and MarvinView: molecule applets for the World Wide Web [Paper presentation]. https://doi.org/10.3390/ecsoc-3-01775
   Google Scholar
• Da Cunha Xavier, J., Ferreira, M. K., A., da Silva, A. W., de Menezes, J. E. S. A., Teixeira, A. M. R., Bandeira, P. N., Bandeira, P. N., Marinho, E. M., Marinho, E. S., Marinho, M. M., & dos Santos, H. S. (2021). Anxiolytic-like and anticonvulsant effect in Adult Zebrafish (Danio rerio) through GABAergic system and molecular docking study of chalcone derived from natural products. Biointerface Research in Applied Chemistry, 11, 14021–14031. 6, https://doi.org/10.33263/BRIAC116.1402114031
   Web of Science ®Google Scholar
• Daina, A., & Zoete, V. (2016). A boiled‐egg to predict gastrointestinal absorption and brain penetration of small molecules. ChemMedChem. 11(11), 1117–1121. https://doi.org/10.1002/cmdc.201600182
   PubMed Web of Science ®Google Scholar
• de Brito, D. H. A., Almeida-Neto, F. W., Ribeiro, L. R., Magalhães, E. P., de Menezes, R. R. B., Sampaio, T. L., Martins, A. M., Bandeira, P. N., Marinho, M. M., Marinho, E. S., Barreto, A. C., de Lima-Neto, P., Saraiva, G. D., Canuto, K. M., dos Santos, H. S., Teixeira, A. M., & Ricardo, N. M. S. (2022). Synthesis, structural and spectroscopic analysis, and antiproliferative activity of chalcone derivate (E)-1-(4-aminophenyl)-3-(benzo [b] thiophen-2-yl) prop-2-en-1-one in Trypanosoma cruzi. Journal of Molecular Structure, 1253, 132197. https://doi.org/10.1016/j.molstruc.2021.132197
   Web of Science ®Google Scholar
• De Menezes, Ramon, R. P. P. B., T. L., Sampaio, D. B., Lima, P. L., Sousa, I. E. P., de Azevedo, E. P., Magalhães, L. D., Tessarolo, M., Machado Marinho, R., Pires dos Santos., & A. M. C., Martins. (2019). Antiparasitic effect of (−)-α-Bisabolol against Trypanosoma Cruzi Y Strain Forms. Diagnostic Microbiology and Infectious Disease, 95(3), 114860. https://doi.org/10.1016/j.diagmicrobio.2019.06.012.
   PubMed Web of Science ®Google Scholar
• de Souza, M. A., de Castro, K. K., Almeida-Neto, F. W., Bandeira, P. N., Ferreira, M. K., Marinho, M. M., da Rocha, M. N., de Brito, D. H., Mendes, F. R. d S., Rodrigues, T. H., de Oliveira, M. R., de Menezes, J. E., Barreto, A. C., Marinho, E. S., de Lima-Neto, P., dos Santos, H. S., & Teixeira, A. M. (2022). Structural and spectroscopic analysis, ADMET study, and anxiolytic-like effect in adult zebrafish (Danio rerio) of 4′-[(1E, 2E)-1-(2-(2′, 4′-dinitrophenyl) hydrazone-3-(4-methoxyphenyl) allyl) aniline. Journal of Molecular Structure, 1251, 132064. https://doi.org/10.1016/j.molstruc.2021.132064
   Web of Science ®Google Scholar
• DeLano, W. L. (2002). Pymol: An open-source molecular graphics tool. CCP4 Newsletter on Protein Crystallography, 40(1), 82–92.
   Google Scholar
• Diaza, R. G., Manganelli, S., Esposito, A., Roncaglioni, A., Manganaro, A., & Benfenati, E. (2015). Comparison of in silico tools for evaluating rat oral acute toxicity. SAR and QSAR in Environmental Research, 26(1), 1–27. https://doi.org/10.1080/1062936X.2014.977819
   PubMed Web of Science ®Google Scholar
• Ditchfield, R. H. W. J., Hehre, W. J., & Pople, J. A. (1971). Self‐consistent molecular‐orbital methods. IX. An extended Gaussian‐type basis for molecular‐orbital studies of organic molecules. The Journal of Chemical Physics, 54(2), 724–728. https://doi.org/10.1063/1.1674902
   Web of Science ®Google Scholar
• El-Wakil, M. H., Khattab, S. N., El-Yazbi, A. F., El-Nikhely, N., Soffar, A., & Khalil, H. H. (2020). New chalcone-tethered 1, 3, 5-triazines potentiate the anticancer effect of cisplatin against human lung adenocarcinoma A549 cells by enhancing DNA damage and cell apoptosis. Bioorganic Chemistry, 105, 104393. https://doi.org/10.1016/j.bioorg.2020.104393
   PubMed Web of Science ®Google Scholar
• Espinoza-Hicks, J. C., Chacón-Vargas, K. F., Hernández-Rivera, J. L., Nogueda-Torres, B., Tamariz, J., Sánchez-Torres, L. E., & Camacho-Dávila, A. (2019). Novel prenyloxy chalcones as potential leishmanicidal and trypanocidal agents: Design, synthesis and evaluation. European Journal of Medicinal Chemistry, 167, 402–413. https://doi.org/10.1016/j.ejmech.2019.02.028
   PubMed Web of Science ®Google Scholar
• Filimonov, D. A., Zakharov, A. V., Lagunin, A. A., & Poroikov, V. V. (2009). QNA-based ‘Star Track’QSAR approach. SAR and QSAR in Environmental Research, 20(7–8), 679–709. https://doi.org/10.1080/10629360903438370
   PubMed Web of Science ®Google Scholar
• Firoozpour, L., Edraki, N., Nakhjiri, M., Emami, S., Safavi, M., Ardestani, S. K., Khoshneviszadeh, M., Shafiee, A., & Foroumadi, A. (2012). Cytotoxic activity evaluation and QSAR study of chromene-based chalcones. Archives of Pharmacal Research, 35(12), 2117–2125. https://doi.org/10.1007/s12272-012-1208-2
   PubMed Web of Science ®Google Scholar
• Frisch, M. J., Trucks, G. W., & Schlegel, H. B. (2009). Gaussian 09, revision A. 02. Gaussian, Inc.
   Google Scholar
• Geysillene Castro Matos, M., da Silva, L. P., Wagner Queiroz Almeida-Neto, F., Machado Marinho, E., Róseo Paula Pessoa Bezerra de Menezes, R., Lima Sampaio, T., Nunes da Rocha, M., Rodrigues Ribeiro, L., Paula Magalhaes, E., Rodrigues Teixeira, A. M., Dos Santos, H. S., Marinho, E. S., de Lima-Neto, P., Costa Martins, A. M., Monteiro, N. K. V., & Machado Marinho, M. (2022). Quantum mechanical, molecular docking, molecular dynamics, ADMET and antiproliferative activity on Trypanosoma cruzi (Y strain) of chalcone (E)-1-(2-hydroxy-3, 4, 6-trimethoxyphenyl)-3-(3-nitrophenyl) prop-2-en-1-one derived from a natural product. Physical Chemistry Chemical Physics : PCCP, 24(8), 5052–5069. https://doi.org/10.1039/D1CP04992E
   PubMed Web of Science ®Google Scholar
• Gillis, E. P., Kyle, J. E., Matthew, D. H., David, J. D., & Nicholas, A. M. (2015). Applications of fluorine in medicinal chemistry. Journal of Medicinal Chemistry, 58(21), 8315–8359. https://doi.org/10.1021/acs.jmedchem.5b00258.
   PubMed Web of Science ®Google Scholar
• González, L. A., Upegui, Y., A., Rivas, L., Echeverri, F., Escobar, G., Robledo, S. M., & Quiñones, W. (2020). Effect of substituents in the A and B rings of chalcones on antiparasite activity. Archiv der Pharmazie, 353(12), 2000157–2000110. https://doi.org/10.1002/ardp.202000157
   Web of Science ®Google Scholar
• Griebler, A., Weyand Banhuk, F., Staffen, I. V., Antunes Maciel Bortoluzzi, A., Soprani Ayala, T., Ferreira Gandra, R., Schuquel, I. T. A., Alves da Silva, E. A., Marinho Jorge, T. C., & Andrade Menolli, R. (2021). Anti-Trypanosoma cruzi activity, cytotoxicity and, chemical characterization of extracts from seeds of Lonchocarpus cultratus. Journal of Infection in Developing Countries, 15(2), 270–279. https://doi.org/10.3855/jidc.12669
   PubMed Web of Science ®Google Scholar
• Han, J., Pei, J., & Tong, H. (2012). Data mining: Concepts and techniques. Morgan Kaufmann, 3, 1–703. https://doi.org/10.1016/C2009-0-61819-5
   Google Scholar
• Hanwell, M. D., Curtis, D. E., Lonie, D. C., Vandermeersch, T., Zurek, E., & Hutchison, G. R. (2012). Avogadro: An advanced semantic chemical editor, visualization, and analysis platform. Journal of Cheminformatics, 4(1), 17. https://doi.org/10.1186/1758-2946-4-17
   PubMed Web of Science ®Google Scholar
• Huey, R., Morris, G. M., Olson, A. J., & Goodsell, D. S. (2007). Software news and update a semiempirical free energy force field with charge-based desolvation. Journal of Computational Chemistry, 28(6), 1145–1152. https://doi.org/10.1002/jcc.20634
   PubMed Web of Science ®Google Scholar
• Hughes, T. B., Miller, G. P., & Swamidass, S. J. (2015). Modeling epoxidation of drug-like molecules with a deep machine learning network. ACS Central Science, 1(4), 168–180. https://doi.org/10.1021/acscentsci.5b00131
   PubMed Web of Science ®Google Scholar
• Imberty, A., Hardman, K. D., Carver, J. P., & Perez, S. (1991). Molecular modelling of protein-carbohydrate interactions. Docking of monosaccharides in the binding site of concanavalin A. Glycobiology, 1(6), 631–642. https://doi.org/10.1093/glycob/1.6.631
   PubMedGoogle Scholar
• Izumi, E., Ueda-Nakamura, T., Dias Filho, B. P., Veiga Junior, V. F., & Nakamura, C. V. (2011). Natural products and Chagas’ disease: A review of plant compounds studied for activity against Trypanosoma cruzi. Natural Product Reports, 28(4), 809–823. https://doi.org/10.1039/c0np00069h
   PubMed Web of Science ®Google Scholar
• Johnson, T. W., Dress, K. R., & Edwards, M. (2009). Using the Golden Triangle to optimize clearance and oral absorption. Bioorganic & Medicinal Chemistry Letters, 19(19), 5560–5564. https://doi.org/10.1016/j.bmcl.2009.08.045
   PubMed Web of Science ®Google Scholar
• Kadela-Tomanek, M., Jastrzębska, M., Marciniec, K., Chrobak, E., Bębenek, E., & Boryczka, S. (2021). Lipophilicity, pharmacokinetic properties, and molecular docking study on SARS-CoV-2 target for betulin triazole derivatives with attached 1, 4-quinone. Pharmaceutics, 13(6), 781. https://doi.org/10.3390/pharmaceutics13060781
   PubMed Web of Science ®Google Scholar
• Lee, C., Yang, W., & Parr, R. G. (1988). Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Review. B, Condensed Matter, 37(2), 785–789. https://doi.org/10.1103/PhysRevB.37.785
   PubMed Web of Science ®Google Scholar
• Lima, J. d R., Ferreira, M. K. A., Sales, K. V. B., da Silva, A. W., Marinho, E. M., Magalhães, F. E. A., Marinho, E. S., Marinho, M. M., da Rocha, M. N., Bandeira, P. N., Teixeira, A. M. R., de Menezes, J. E. S. A., & dos Santos, H. S. (2021). Diterpene Sonderianin isolated from Croton blanchetianus exhibits acetylcholinesterase inhibitory action and anxiolytic effect in adult zebrafish (Danio rerio) by 5-HT system. Journal of Biomolecular Structure and Dynamics, 39, 1–16. https://doi.org/10.1080/07391102.2021.1991477
   PubMedGoogle Scholar
• Lipinski, C. A. (2004). Lead-and drug-like compounds: the rule-of-five revolution. Drug Discovery Today. Technologies, 1(4), 337–341. https://doi.org/10.1016/j.ddtec.2004.11.007
   PubMedGoogle Scholar
• Magalhães, E. P., Gomes, N. D. B., Freitas, T. A. d., Silva, B. P., Ribeiro, L. R., Ameida-Neto, F. W. Q., Marinho, M. M., Lima-Neto, P. d., Marinho, E. S., Santos, H. S. D., Teixeira, A. M. R., Sampaio, T. L., Menezes, R. R. P. P. B. d., & Martins, A. M. C. (2022). Chloride substitution on 2-hydroxy-3, 4, 6-trimethoxyphenylchalcones improves in vitro selectivity on Trypanosoma cruzi strain Y. Chemico-Biological Interactions, 361, 109920. https://doi.org/10.1016/j.cbi.2022.109920
   PubMed Web of Science ®Google Scholar
• Marinho, E. M., de Andrade Neto, J. B., Silva, J., da Silva, C. R., Cavalcanti, B. C., Marinho, E. S., & Júnior, H. V. N. (2020). Virtual screening based on molecular docking of possible inhibitors of Covid-19 main protease. Microbial Pathogenesis, 148, 104365. https://doi.org/10.1016/j.micpath.2020.104365
   PubMed Web of Science ®Google Scholar
• Martin, Y. C. (2005). A bioavailability score. Journal of Medicinal Chemistry, 48(9), 3164–3170. https://doi.org/10.1021/jm0492002
   PubMed Web of Science ®Google Scholar
• Morris, G. M., Huey, R., Lindstrom, W., Sanner, M. F., Belew, R. K., Goodsell, D. S., & Olson, A. J. (2009). AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. Journal of Computational Chemistry, 30(16), 2785–2791. https://doi.org/10.1002/jcc.21256
   PubMed Web of Science ®Google Scholar
• Müller, Z. K., Christoph, F., & François, D. (2007). Fluorine in pharmaceuticals: Looking beyond intuition. Science (New York, N.Y.), 317(5846), 1881–1886. https://doi.org/10.1126/SCIENCE.1131943/SUPPL_FILE/MULLER.SOM.PDF.[PMC][17901324
   PubMed Web of Science ®Google Scholar
• Newby, D., Freitas, A. A., & Ghafourian, T. (2015). Decision trees to characterise the roles of permeability and solubility on the prediction of oral absorption. European Journal of Medicinal Chemistry, 90, 751–765. https://doi.org/10.1016/j.molstruc.2021.132064[PMC][25528330
   PubMed Web of Science ®Google Scholar
• Nguyen, D. D., Xiao, T., Wang, M., & Wei, G. W. (2017). Rigidity strengthening: A mechanism for protein–ligand binding. Journal of Chemical Information and Modeling, 57(7), 1715–1721. https://doi.org/10.1021/acs.jcim.7b00226
   PubMed Web of Science ®Google Scholar
• Ortalli, M., Ilari, A., Colotti, G., De Ionna, I., Battista, T., Bisi, A., Gobbi, S., Rampa, A., Di Martino, R. M. C., Gentilomi, G. A., Varani, S., & Belluti, F. (2018). Identification of chalcone-based antileishmanial agents targeting trypanothione reductase. European Journal of Medicinal Chemistry, 152, 527–541. https://doi.org/10.1016/j.ejmech.2018.04.057
   PubMed Web of Science ®Google Scholar
• Pariona-Llanos, R., Raphael, S. P., Marcelo, R., Vincent, N., Ariel, M. S., Hugo, A. A., Maria, I., Nogueira, C., & Maria, C. E. (2015). Glyceraldehyde 3-phosphate dehydrogenase-telomere association correlates with redox status in Trypanosoma Cruzi. PLoS One. 10(3), e0120896. https://doi.org/10.1371/journal.pone.0120896
   PubMed Web of Science ®Google Scholar
• Pavão, F., Castilho, M. S., Pupo, M. T., Dias, R. L. A., Correa, A. G., Fernandes, J. B., da Silva, M. F. G. F., Mafezoli, J., Vieira, P. C., & Oliva, G. (2002). Structure of Trypanosoma cruzi glycosomal glyceraldehyde-3-phosphate dehydrogenase complexed with chalepin, a natural product inhibitor, at 1.95 Å resolution. FEBS Letters, 520(1–3), 13–17. https://doi.org/10.1016/S0014-5793(02)02700-X
   PubMed Web of Science ®Google Scholar
• Pérez-Molina, J. A., Pérez-Ayala, A., Moreno, S., Fernandez-Gonzalez, M. C., Zamora, J., & Lopez-Velez, R. (2009). Use of benznidazole to treat chronic Chagas’ disease: A systematic review with a meta-analysis. The Journal of Antimicrobial Chemotherapy, 64(6), 1139–1147. https://doi.org/10.1093/jac/dkp357
   PubMed Web of Science ®Google Scholar
• Pettersen, E. F., Goddard, T. D., Huang, C. C., Couch, G. S., Greenblatt, D. M., Meng, E. C., & Ferrin, T. E. (2004). UCSF Chimera—a visualization system for exploratory research and analysis. Journal of Computational Chemistry, 25(13), 1605–1612. https://doi.org/10.1002/jcc.20084
   PubMed Web of Science ®Google Scholar
• Pires, D. E., Kaminskas, L. M., & Ascher, D. B. (2018). Prediction and optimization of pharmacokinetic and toxicity properties of the ligand. In Computational drug discovery and design (pp. 271–284). Humana Press. https://doi.org/10.1007/978-1-4939-7756-7_14
   Google Scholar
• Purser, R. S., Peter, R. M., Steve, S., & Véronique, G. (2008). Fluorine in Medicinal Chemistry. Chemical Society Reviews, 37(2), 320–330. https://doi.org/10.1039/B610213C.
   PubMed Web of Science ®Google Scholar
• Radchenko, E. V., Rulev, Y. A., Safanyaev, A. Y., Palyulin, V. A., & Zefirov, N. S. (2017). Computer-aided estimation of the hERG-mediated cardiotoxicity risk of potential drug components. Doklady. Biochemistry and Biophysics, 473(1), 128–131. (Pleiades Publishing. https://doi.org/10.1134/S1607672917020107
   PubMed Web of Science ®Google Scholar
• Ritchie, T. J., & Macdonald, S. J. (2009). The impact of aromatic ring count on compound developability–are too many aromatic rings a liability in drug design? Drug Discovery Today. 14(21-22), 1011–1020. https://doi.org/10.1016/j.drudis.2009.07.014
   PubMed Web of Science ®Google Scholar
• Rocha, J. E., de Freitas, T. S., da Cunha Xavier, J., Pereira, R. L. S., Junior, F. N. P., Nogueira, C. E. S., Marinho, M. M., Bandeira, P. N., de Oliveira, M. R., Marinho, E. S., Teixeira, A. M. R., Dos Santos, H. S., & Coutinho, H. D. M. (2021). Antibacterial and antibiotic modifying activity, ADMET study and molecular docking of synthetic chalcone (E)-1-(2-hydroxyphenyl)-3-(2, 4-dimethoxy-3-methylphenyl) prop-2-en-1-one in strains of Staphylococcus aureus carrying NorA and MepA efflux pumps. Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie, 140, 111768. https://doi.org/10.1016/j.biopha.2021.111768
   PubMed Web of Science ®Google Scholar
• Rodriguez, S. V., Guíñez, R. F., Matos, M. J., Azar, C. O., Maya, J. D., Uriarte, E., Santana, L., & Borges, F. (2015). Synthesis and trypanocidal properties of new coumarin-chalcone derivatives. Medicinal Chemistry, 5(4), 173–177. https://doi.org/10.4172/2161-0444.1000260
   Google Scholar
• Salmazzo, G. R., Verdan, M. H., Silva, F., Cicarelli, R. M., Mota, J. d S., Salvador, M. J., de Carvalho, J. E., & Cardoso, C. A. L. (2021). Chemical composition and antiproliferative, antioxidant and trypanocidal activities of the fruits from Campomanesia xanthocarpa (Mart.) O. Berg (Myrtaceae). Natural Product Research, 35(5), 853–857. https://doi.org/10.1080/14786419.2019.1607333
   PubMed Web of Science ®Google Scholar
• Sanchez, A. M., Jimenez-Ortiz, V., Sartor, T., Tonn, C. E., García, E. E., Nieto, M., Burgos, M. H., & Sosa, M. A. (2006). A novel icetexane diterpene, 5-epi-icetexone from Salvia gilliessi is active against Trypanosoma cruzi. Acta Tropica, 98(2), 118–124. https://doi.org/10.1016/j.actatropica.2005.12.007
   PubMed Web of Science ®Google Scholar
• Saravanamuthu, A., Vickers, T. J., Bond, C. S., Peterson, M. R., Hunter, W. N., & Fairlamb, A. H. (2004). Two interacting binding sites for quinacrine derivatives in the active site of trypanothione reductase: a template for drug design. The Journal of Biological Chemistry, 279(28), 29493–29500. https://doi.org/10.1074/jbc.M403187200
   PubMed Web of Science ®Google Scholar
• Sarma, R. H. (1997). Journal of biomolecular structure and dynamics. Journal of Biomolecular Structure & Dynamics, 15(3), 634–634. https://doi.org/10.1016/j.actatropica.2019.04.024
   PubMed Web of Science ®Google Scholar
• Shityakov, S., & Foerster, C. (2014). In silico predictive model to determine vector-mediated transport properties for the blood–brain barrier choline transporter. Advances and Applications in Bioinformatics and Chemistry, 2014, 7, 23–36. https://doi.org/10.2147/AABC.S63749
   Google Scholar
• Silva Mendes, F. R., Wlisses da Silva, A., Amâncio Ferreira, M. K., de Lima Rebouças, E., Marinho, E. M., Marinho, M. M., Bandeira, P. N., Rodrigues Teixeira, A. M., Silva Alencar de Menezes, J. E., Alves de Siqueira, E., Róseo Paula Pessoa Bezerra de Menezes, R., Marinho, E. S., & Silva Dos Santos, H. (2022). GABAA receptor participation in anxiolytic and anticonvulsant effects of (E)-3-(furan-2-yl)-1-(2hydroxy-3,4,6-trimethoxyphenyl)prop-2-en-1-one in adult zebrafish. Neurochemistry International, 155, 105303. https://doi.org/10.1016/j.neuint.2022.105303
   PubMed Web of Science ®Google Scholar
• Silva, J., Esmeraldo Rocha, J., da Cunha Xavier, J., Sampaio de Freitas, T., Douglas Melo Coutinho, H., Nogueira Bandeira, P., Rodrigues de Oliveira, M., Nunes da Rocha, M., Machado Marinho, E., de Kassio Vieira Monteiro, N., Ribeiro, L. R., Róseo Paula Pessoa Bezerra de Menezes, R., Machado Marinho, M., Magno Rodrigues Teixeira, A., Silva Dos Santos, H., & Silva Marinho, E. (2022). Antibacterial and antibiotic modifying activity of chalcone (2E)-1-(4–aminophenyl)-3-(4-methoxyphenyl)-prop-2-en-1-one in strains of Staphylococcus aureus carrying NorA and MepA efflux pumps: In vitro and in silico approaches. Microbial Pathogenesis, 169, 105664. https://doi.org/10.1016/j.micpath.2022.105664
   PubMed Web of Science ®Google Scholar
• Swallow, S. (2015). Fluorine in medicinal chemistry. Progress in Medicinal Chemistry, 54, 65–133. https://doi.org/10.1016/BS.PMCH.2014.11.001.
   PubMedGoogle Scholar
• Trott, O., & Olson, A. J. (2010). AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. Journal of Computational Chemistry, 31(2), 455–461. https://doi.org/10.1002/jcc.21334
   PubMed Web of Science ®Google Scholar
• Ušjak, D., Ivković, B., Božić, D. D., Bošković, L., & Milenković, M. (2019). Antimicrobial activity of novel chalcones and modulation of virulence factors in hospital strains of Acinetobacter baumannii and Pseudomonas aeruginosa. Microbial Pathogenesis, 131, 186–196. https://doi.org/10.1016/j.micpath.2019.04.015
   PubMed Web of Science ®Google Scholar
• Vázquez, K., Margot, P., Cristian, O. S., Juan, J. Z., R., Brenda, V., & Gildardo, R. (2017). Trypanothione reductase: A target for the development of anti-Trypanosoma Cruzi drugs. Mini Reviews in Medicinal Chemistry, 17(11), 939–946. https://doi.org/10.2174/1389557517666170315145410.
   PubMed Web of Science ®Google Scholar
• Veber, D. F., Johnson, S. R., Cheng, H. Y., Smith, B. R., Ward, K. W., & Kopple, K. D. (2002). Molecular properties that influence the oral bioavailability of drug candidates. Journal of Medicinal Chemistry, 45(12), 2615–2623. https://doi.org/10.1021/jm020017n
   PubMed Web of Science ®Google Scholar
• Wager, T. T., Hou, X., Verhoest, P. R., & Villalobos, A. (2016). Central nervous system multiparameter optimization desirability: application in drug discovery. ACS Chemical Neuroscience, 7(6), 767–775. https://doi.org/10.1021/acschemneuro.6b00029
   PubMed Web of Science ®Google Scholar
• Wheatley, D. E., Clement, Q. F., Ramakrishna, K., Robert, S., Edward, L. B., Jean, B., Vendeville, N. J., Wells, M. E. L., & Bruno, L. (2021). Synthesis and structural characteristics of all mono- and difluorinated 4,6-dideoxy-d-xylo-hexopyranoses. The Journal of Organic Chemistry, 86(11), 7725–7756. https://doi.org/10.1021/ACS.JOC.1C00796.
   PubMed Web of Science ®Google Scholar
• Wu, Z., Lei, T., Shen, C., Wang, Z., Cao, D., & Hou, T. (2019). ADMET evaluation in drug discovery. 19. Reliable prediction of human cytochrome P450 inhibition using artificial intelligence approaches. Journal of Chemical Information and Modeling, 59(11), 4587–4601. https://doi.org/10.1021/acs.jcim.9b00801
   PubMed Web of Science ®Google Scholar
• Yan, J., Zhang, G., Pan, J., & Wang, Y. (2014). α-Glucosidase inhibition by luteolin: Kinetics, interaction and molecular docking. International Journal of Biological Macromolecules, 64, 213–223. https://doi.org/10.1016/j.ijbiomac.2013.12.007
   PubMed Web of Science ®Google Scholar
• Yu, K., Geng, X., Chen, M., Zhang, J., Wang, B., Ilic, K., & Tong, W. (2014). High daily dose and being a substrate of cytochrome P450 enzymes are two important predictors of drug-induced liver injury. Drug Metabolism and Disposition, 42(4), 744–750. https://doi.org/10.1124/dmd.113.056267
   PubMed Web of Science ®Google Scholar
• Yusuf, D., Davis, A. M., Kleywegt, G. J., & Schmitt, S. (2008). An alternative method for the evaluation of docking performance: RSR vs RMSD. Journal of Chemical Information and Modeling, 48(7), 1411–1422. https://doi.org/10.1021/ci800084x
   PubMed Web of Science ®Google Scholar
• Zheng, M., Luo, X., Shen, Q., Wang, Y., Du, Y., Zhu, W., & Jiang, H. (2009). Site of metabolism prediction for six biotransformations mediated by cytochromes P450. Bioinformatics (Oxford, England), 25(10), 1251–1258. https://doi.org/10.1093/bioinformatics/btp140
   PubMed Web of Science ®Google Scholar
• Zheoat, A. M., Alenezi, S., Elmahallawy, E. K., Ungogo, M. A., Alghamdi, A. H., Watson, D. G., Igoli, J. O., Gray, A. I., de Koning, H. P., & Ferro, V. A. (2021). Antitrypanosomal and antileishmanial activity of chalcones and flavanones from Polygonum salicifolium. Pathogens, 10(2), 175–179. https://doi.org/10.3390/pathogens10020175
   PubMed Web of Science ®Google Scholar