Synthesis, antimicrobial activity and silicon study of 1,2,4-oxadiazoles derived from of ethyl levulinate
Abstract
This study describes the synthesis, antimicrobial activity, and in silico assessment of 1,2,4-oxadiazoles from ethyl levulinate. For that, we prepared arylamidoximes and treated them with ethyl levulinate, obtaining the respective 1,2,4-oxadiazoles through a reaction sequence of O-acylation followed by cyclodehydration. Then, we assessed the antimicrobial activity of these compounds against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, Pseudomonas aeruginosa, and Candida utilis using the broth microdilution technique. We analyzed in silico studies using the online bioinformatics platforms SwissADME and PASS. We obtained arylamidoximes and 1,2,4-oxadiazoles in good yields. The 1,2,4-oxadiazoles showed moderate antimicrobial activity, inhibiting two microorganisms: the bacterium P. aeruginosa and the fungus C. utilis. In silico studies of 1,2,4-oxadiazoles have shown promising properties, such as good oral absorption, low probability of toxicity, good body distribution, and potential to develop metabolic and enzymatic activities. The investigation of the antimicrobial activity together with the in silico studies showed that the synthesized 1,2,4-oxadiazoles are promising structures for the development of new therapeutic agents.
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References
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Bussmeyer,E. C., & Henkes, J. A. (2015). Gestão ambiental na indústria do petróleo: sistema de gestão ambiental nas sondas de perfuração. Revista Gestão & Sustentabilidade Ambiental 3(2), 396-462.
Anuário estatístico brasileiro do petróleo, gás natural e biocombustíveis. (2016). PETROBRAS. Agência Nacional do Petróleo, Gás Natural e Biocombustíveis (ANP). Bussmeyer, E. C. (2015). Gestão ambiental na indústria do petróleo: sistema de gestão ambiental nas sondas de perfuração. Revista Gestão e Sustentabilidade Ambiental, 3(2), 396 -462. doi: 10.19177/rgsa.v3e22014396-462
Frank, R. A, Fischer, K., Kavanagh, R., Burnison, K., Arsenault, G., Headley, J. V., Peru, K. M., Van der Kraak, G. & Solomon, K. R. (2009). Effect of carboxylic acid content on the acute toxicity of oil sands naphthenic acids. Environmental Science & Technology, 43(2), 266-271. doi: 10.1021/es8021057
Ghimire, N. & Wang, S. (2018). Biological Treatment of Petrochemical Wastewater. Petroleum Chemicals - Recent Insight. Intechopen, doi: 10.5772/intechopen.79655
Giles, C. H., Macewan, T. H., Nakhwa, S. N.& Smith, D. (1960). Studies in adsorption. Part XI. A system of classification of solution adsorption isotherms, and its use in diagnosis of adsorption mechanisms and in measurement of specific surface areas of solids. Journal of the Chemical Society (Resumed), 846, 3973–3993. doi: 10.1039/JR9600003973
Headley, J. V., Peru, K. M., Barrow, M. P. & Derrick, P. J. (2007). Characterization of naphthenic acids from Athabasca oil sands using electrospray ionization: the significant influence of solvents. Analytical Chemistry, 79(16), 6222-6229. doi: 10.1021/ac070905w
Ho, Y. S. & Mckay, G. (1999) Pseudo-second order model for sorption processes. Process Biochemistry, 34(5), 451-465. doi: 10.1016/S0032-9592(98)00112-5
Islam, M., McPhedran, K. N., Messele, S. A., Liu, Y. & El-Din, M. G. (2018). Isotherm and kinetic studies on adsorption of oil sands process-affected water organic compounds using granular activated carbon. Chemosphere, 202, 716-725. doi: https://doi.org/10.1016/j.chemosphere.2018.03.149
Jesus, F. A., Silva, J. V., Santos, T. M., Silva, M. S., Aragão, M. G. B. & Silva, G. F. (2019). An evaluation of different preparation methods of the M. Oleífera-based natural coagulating agent in the treatment of produced water from petroleum. Águas Subterrâneas, 33, 221-228. doi: 10.14295/ras.v33i2.29197
Khan, M. K., Riaz, A., Yi, M. & Kim, J. (2017). Removal of naphthenic acids from high acid crude via esterification with methanol. Fuel Process Technology, 165,123-130. doi: 10.1016/j.fuproc.2017.05.015
Martinez-Iglesias, A., Niasar, S. H., Xu, C. & Ray, B. M. (2015). Adsorption of Model Naphthenic Acids in Water with Granular Activated Carbon. Adsorption Science Technology, 33(10), 881-894. doi: 10.1260/0263-6174.33.10.881
Nasir Shah, S, Mutalib, M. I. A., Pilus, R. B. M. & Lethesh, K. C. (2014). Extraction of naphthenic acid from highly acidic oil using hydroxide-based ionic liquids. Energy Fuels, 29(1), 106-111. doi: 10.1021/ef502169q
Niasar, H. S., Li, H., Kasanneni, T. V. R., Ray, M. B. & Xu, C. C. (2016). Surface amination of activated carbon and petroleum coke for the removal of naphthenic acids and treatment of oil sands process-affected water (OSPW). Chemical Engineering Journal, 293, 189-199. doi: 10.1016/j.cej.2016.02.062
Santaella, S.T., Silva, F.C.G., Costa, K.O., Aguiar, R., Arthaud, I.D.B., Leitão, R. C. (2009). Tratamento de efluentes de refinaria de petróleo em reatores com Aspergillus niger. Engenharia Sanitária Ambiental, 14(1): 139-148. doi: 10.1590/S1413-41522009000100015
Santo, C. (2010). A indústria de refinação de petróleo: características e tratamento das águas residuais. e-LP Engineering and Technology Journal, 1.
Varadaraj, R. & Brons, C. (2007). Molecular origins of heavy crude oil interfacial activity part 2: Fundamental interfacial properties of model naphthenic acids and naphthenic acids separated from heavy crude oils. Energy Fuels, 21(1), 199-204. doi: 10.1021/ef0604240
Wu, J., Montes, V., Virla, L. D. & Hill, J. M. (2018). Impacts of amount of chemical agent and addition of steam for activation of petroleum coke with KOH or NaOH. Fuel Processing Technology, 181, 53-60. doi: 10.1016/j.fuproc.2018.09.018
Yang, S., Wang, F., Tanga, Q., Wang, P., Xu, Z. & Liang, J. (2019). Utilization of ultralight carbon foams for the purification of emulsified oil wastewater and their adsorption kinetics. Chemical Physics, 516, 139-146. doi: 10.1016/j.chemphys.2018.08.051
Yassine, M. M. & Dabek-Zlotorzynska, E. (2017). Application of ultrahigh-performance liquid chromatography–quadrupole time-of-flight mass spectrometry for the characterization of organic aerosol: searching for naphthenic acids. Journal of Chromatography A, 1512, 22-33. doi: 10.1016/j.chroma.2017.06.067
Yu, L., Han, M. & He, F. (2017). A review of treating oily wastewater. Arabian Journal of Chemistry, 10, 1913-1922. doi: 10.1016/j.arabjc.2013.07.020
Andrade, D., Freitas Filho, J. R. & Freitas, J. C. R. (2016) Aplicação de amidoximas como catalisadores da reação de alilação por aliltrifluoroborato de potássio em meio bifásico. Química Nova, 39(10), 1225-1235. doi: 10.21577/0100-4042.20160158.
Barreiro, E. J. & Fraga, C. A. M. (2014) Química Medicinal: As bases moleculares da ação dos fármacos (3 ed.). Porto Alegre: Artmed.
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, 3(3), 435–444. doi: 10.1002/cmdc.200700139
CDC. (2019) Antibiotic Resistance Threats in the United States, 2019. Atlanta, GA: U.S. Department of Health and Human Services, CDC.
Chaves, J. D. S., Tunes, L. G., Franco, C. H. D. J., Francisco, T. M., Corrêa, C. C., Murta, S. M., Monte-Neto, R. L., Silva, H., Fontes, A. P. S. & Almeida, M. V. (2017) Novel gold(I) complexes with 5-phenyl-1,3,4-oxadiazole-2-thione and phosphine as potential anticancer and antileishmanial agents. European Journal of Medicinal Chemistry, 127, 727-739. doi: 10.1016/j.ejmech.2016.10.052
Cunha, F.S., Nogueira, J. M. R. & Aguiar, A. P. (2018) Synthesis and Antibacterial Evaluation of 3,5-Diaryl-1,2,4-oxadiazole Derivatives. Journal of the Brazilian Chemical Society, 29(11), 2405-2416. doi: 10.21577/0103-5053.20180118
Daina, A., Michielin, O. & Zoete, V. (2017) SwissADME: a free web tool to evaluate pharmacokinetics, druglikeness and medicinal chemistry friendliness of small molecules. Scientific Reports, 7(1), 42717. doi: 10.1038/srep42717
Espinel-ingroff, A., Fothergill, A., Ghannoum, M., Manavathu, E., Ostrosky-Zeichner, L., Pfaller, M., Rinaldi, M., Schell, W. & Walsh, T. (2005) Quality Control and Reference Guidelines for CLSI Broth Microdilution Susceptibility Method (M38-A Document) for Amphotericin B, Itraconazole, Posaconazole, and Voriconazole. Journal of Clinical Microbiology, 43(10), 5243-5246. doi: 10.1128/JCM.43.10.5243–5246
Faizi, M., Sheikhha, M., Ahangar, N., Ghomi, H.T., Shafaghi, B., Shafiee, A. & Tabatabai, A. S. (2012) Design, Synthesis and Pharmacological Evaluation of Novel 2-[2-(2-Chlorophenoxy) phenyl]-1,3,4-oxadiazole Derivatives as Benzodiazepine Receptor Agonists. Iranian Journal of Pharmaceutical Research, 11(1), 83–90. doi: 10.22037/IJPR.2012.1066
Freitas, J. J. R., Freitas, J. C. R., Silva, L. P., Freitas Filho, J. R. Kimuraa, G. Y. V., Srivastava, R. M.(2007) Microwave-induced one-pot synthesis of 4-[3-(aryl)-1,2,4-oxadiazol-5-yl]-butan-2-ones under solvent free conditions. Tetrahedron Letters, 48 (35), 6195–6198. doi: 10.1016/j.tetlet.2007.06.116
Freitas, J. J. R., Silva, E. E., Regueira, J. L. L. F., de Andrade, S. A., Calvalcante, P. M. M., Oliveira, R. N. & Freitas Filho, J. R. (2012) 1,2,4-Oxadiazóis: Síntese e aplicações. Revista Virtual Química, 4(6),670-691. doi: 10.5935/1984-6835.20120051
Golan, D. E., Tashjian Junior, A. H., Armstrong, E. J. & Armstrong, A. W. (2014) Princípios de farmacologia: a base fisiopatológica da farmacoterapia (3 ed.). Rio de Janeiro: Guanabara Koogan.
Krishna, C., Bhargavi, M. V., Rao, C. P. & Krupadanam, G. L. D. (2015) Synthesis and antimicrobial assesment of novel coumarins featuring 1,2,4-oxadiazole. Medicinal Chemistry Researach, 24(10), 3743-3751. doi: 10.1007/s00044-015-1399-4
Lee, H. & Lee, D. G. (2018) Novel Approach into Efficient Antifungal Drug Action. Journal of microbiology and biotechnology, 28(11), 1771-1781. doi: 10.4014/jmb.1807.07002
Leite, A. C. L., Vieira, R.F., Faria, A. R., Wanderley, A.G., Afiatpour, P., Ximenes, E. C. P. A., Srivastava, R.M., Oliveira, C.F., Medeiros, M.V., Antunes, E. & Brondani, D.J. (2000) Synthesis, anti-inflammatory and antimicrobial activities of new 1,2,4-oxadiazoles peptidomimetics. Il Farmaco, 55(11-12), 719-724. doi.org/10.1016/S0014-827X(00)00099-9
Lipinski, C. A. (2004) Lead and drug-like compounds: the rule-of-five revolution. Drug Discovery today: Technologies, 1(4), 337-341. doi: 10.1016/j.ddtec.2004.11.007
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Published
2020-09-28
How to Cite
DA CUNHA LIMA, Josefa Aqueline et al.
Synthesis, antimicrobial activity and silicon study of 1,2,4-oxadiazoles derived from of ethyl levulinate.
Acta Brasiliensis, [S.l.], v. 4, n. 3, p. 161-167, sep. 2020.
ISSN 2526-4338.
Available at: <http://revistas.ufcg.edu.br/actabra/index.php/actabra/article/view/390>. Date accessed: 26 nov. 2024.
doi: https://doi.org/10.22571/2526-4338390.
Section
Pharmacy
