Síntese, caracterização e avaliação antimicrobiana de 1,2,4-oxadiazóis derivados do ácido trans-3,4-(metilenodioxi)-cinâmico
DOI:
https://doi.org/10.22571/2526-4338555Palavras-chave:
1,2,4-Oxadiazol, ácido cinâmico, amidoxime, antibacterinaResumo
Os compostos que contêm sistemas de anéis heterocíclicos são de grande importância tanto na medicina quanto na indústria. O anel heterocíclico de 1,2,4-oxadiazol de cinco membros tem recebido atenção considerável por causa de suas propriedades bioisostéricas únicas e um espectro excepcionalmente amplo de atividades biológicas. Este estudo teve como objetivo a síntese, a caracterização e a avaliação da atividade antimicrobiana de uma série de 2-(3-aril-1,2,4-oxadiazol-5-il)-trans-3,4-(metilenodioxi)-cinamila usando modelos experimentais in vitro. A síntese dos 1,2,4-oxadiazóis foi desenvolvida, com duração de 5 min, usando irradiação de micro-ondas fornecendo os compostos em rendimentos moderados (34-50%). Suas estruturas foram determinadas usando espectroscopia de IV (Infravermelho), Resonância magnética nuclear de hidrogênio (RMN 1H) () eRessonancia magnética nuclear de carbono 13 (RMN 13C). As atividades antibacterianas dos novos derivados de 1,3,4-oxadiazóis foram testado contra Gram positivo (Bacillus subtilis, Enterococcus faecalis e Staphylococcus aureus) e Gram negativo (Escherichia coli e Klebsiella pneumoniae) bactérias usando o método de difusão em disco. Os 2-(3-m-toluil-1,2,4-oxadiazol-5-il)-3,4-(metilenodioxi)-cinamila e o 2-(3-pirimidil-1,2,4-oxadiazol-5-il)-3,4-(metilenodioxi)- cinamila apresentaram resultados contra S. aureus, com valor de CIM de 19,5 μg mL-1 quatro vezes mais potente que o metronidazol padrão (CIM=78 μg mL-1).
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Referências
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Baral, N., Mohapatra, S., Raiguru, B. P., Mishra, N. P., Panda, P., Nayak, S., Pandey, S. K., Kumar, P. S., &Sahoo, C. R.J. (2019). Microwave-Assisted Rapid and Efficient Synthesis of New Series of Chromene-Based 1,2,4-Oxadiazole Derivatives and Evaluation of Antibacterial Activity with Molecular Docking Investigation. Heterocyclic Chem, 56, 552-565. https://doi.org/10.1002/jhet.3773
Bezerra, N. M. M., De Oliveira, S. P., Srivastava, R. M., &da Silva, J. R. (2005). An easy synthesis of 3,5-disubstituted 1,2,4-oxadiazoles from carboxylic acids and arylamidoximes mediated by ethyl chloroformate. II Farmaco, 60, 955. http://dx.doi.org/10.1016/j.farmac.2005.08.003
Biernacki, K., Dásko, M., Ciupak, O., Kubinsk, K. Rachon, J., Demkowicz, S. (2020). Novel 1,2,4-Oxadiazole Derivatives in Drug Discovery. Pharmaceuticals, 13(6), 1-45. https://doi.org/10.3390/ph13060111
Bora, R. O., Dar, B., Pradhan, V., & Farooqui, M. (2014). 1, 2, 4-oxadiazoles: synthesis and biological applications. Mini-reviews in Medicinal Chemistry, 14(4), 355-369. doi: 10.2174 / 1389557514666140329200745
Brotschi, C., Roch, C., Gatfield, J., Treiber, A., Williams, J. T., Sifferlen, T., Heidmann, B., Jenck, F., Bolli, M. H., &Boss, C. (2019). Oxadiazole Derivatives as Dual Orexin Receptor Antagonists: Synthesis, Structure-Activity Relationships, and Sleep-Promoting Properties in Rats. ChemMedChem, 14, 1257-1270, doi:10.1002/cmdc.201900242.
Chernyshov, V. V., Yarovaya, O. I., Esaulkova, I. L., Sinegubova, E. Borisevich, S. S., Popadyuk, I. I., Zarubaev, V. V., &Salakhutdinov, N. F. (2022). Novel O-acylated amidoximes and substituted 1,2,4-oxadiazoles synthesised from (+)-ketopinic acid possessing potent virus-inhibiting activity against phylogenetically distinct influenza A viruses. Bioorganic & Medicinal Chemistry Letters, 1(55), 128465. doi: 10.1016/j.bmcl.2021.128465. Epub 2021 Nov 19. PMID: 34808389
Clinical and Laboratory Standards Institute. (2010). Performance standards for antimicrobial susceptibility testing, Document M100-S20, 2010. Wayne, PA.
De Vita, D., Friggeri, L., D'Auria, F. D., Pandolfi, F., Piccoli, F., Panella, S., Palamara, A. T., Simonetti, G., Scipione, L., Di Santo, R., Costi, R., & Tortorella, S. (2014). Activity of caffeic acid derivatives against Candida albicans biofilm. Bioorganic & medicinal chemistry letters, 24(6), 1502-1505. https://doi.org/10.1016/j.bmcl.2014.02.005
Debnath, B., Samanta, S., Roy, K., & Jha, T. (2003). QSAR study on some p-arylthio cinnamides as antagonists of biochemical ICAM-1/LFA-1 interaction and ICAM-1/JY-8 cell adhesion in relation to anti-inflammatory activity. Bioorganic & medicinal chemistry, 11(8), 1615-1619. https://doi.org/10.1016/s0968-0896(03)00085-3
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. https://doi.org/10.1128/JCM.43.10.5243-5246.2005
Farooqui, M., Bora, R., &Patil, C. R. (2009). Synthesis, analgesic and anti-inflammatory activities of novel 3-(4-acetamido-benzyl)-5-substituted-1,2,4-oxadiazoles. European Journal of Medicinal Chemistry, 44(2), 794-799. doi: 10.1016/j.ejmech.2008.05.022
Gobec, M., Tomašič, T., Markovič, T., Mlinarič-Raščan, I., Dolenc, M. S., Jakopin, Ž. (2015). Antioxidant and anti-inflammatory properties of 1,2,4-oxadiazole analogs of resveratrol. Chemico-Biological Interactions, 240, 200-207. doi: 10.1016/j.cbi.2015.08.018
Haugwitz, R.D., Martinez, A. J., Venslavsky, J., Angel, R. G., Maurer, B. V., Jacobs, G. A., Narayanan, V. L., Cruthers, L. R., &Szanto, J. (1985). Antiparasitic agents. 6. Synthesis and anthelmintic activities of novel isothiocyanatophenyl-1,2,4-oxadiazoles. J Med Chem, 28(9), 1234-41. doi: 10.1021/jm00147a019
Ibrahim, T. S., Almalki, A. J., Moustafa, A. H., Allam R. M., Abuo-Rahma, G. E-D. A., El Subbagh, H. I., &Mohamed, M. F. A. (2011). Novel 1,2,4-oxadiazole-chalcone/oxime hybrids as potential antibacterial DNA gyrase inhibitors: Design, synthesis, ADMET prediction and molecular docking study. Bioorganic Chemistry, 111, 104885. https://doi.org/10.1016/j.bioorg.2021.104885
Kumar, D., Patel, G., Chavers, A. K., Chang, K.-H., &Shah, K. (2011). Synthesis of novel 1,2,4-oxadiazoles and analogues as potential anticancer agents. European Journal of Medicinal Chemistry. 46(7), 3085-3092.http://dx.doi.org/10.1016/j.ejmech.2011.03.031
Lima, J. A. C., Costa, E. C.S., Bezerra, G. B., Silva, J. F., Rodrigo Caina, R. A., de Freitas Filho, J. R., & Freitas, J. C. R. (2020) Synthesis, antimicrobial activity, and in silico studies of 1,2,4-oxadiazoles from ethyl levulinate. Acta Brasiliensis, 4(3), 161-167. DOI: https://doi.org/10.22571/2526-4338390
Liu, Q., Zhu, R., Gao, S., Ma, S.-H., Tang, H.-J., Yang, J.-J., Diao, Y.-M., Wang, H.-L. and Zhu, H.-J. (2017), Structure-based bioisosterism design, synthesis, insecticidal activity and structure-activity relationship (SAR) of anthranilic diamide analogues containing 1,2,4-oxadiazole rings. Pest Management Science, 73, 917-924. https://doi.org/10.1002/ps.4363
Maftei, C. V., Fodor, E., Jones, P. G., Franz, M. H., Kelter, G., Fiebig, H., &Neda, I. (2013). Synthesis and characterization of novel bioactive 1,2,4-oxadiazole natural product analogs bearing the N-phenylmaleimide and N-phenylsuccinimide moieties. Beilstein Journal of Organic Chemistry, 9, 2202-2215. https://doi.org/10.3762/bjoc.9.259.
Mohammadi-Khanaposhtani, M, Shabani, M., Faizi, M., &Aghaei, I. (2016). Design, synthesis, pharmacological evaluation, and docking study of new acridone-based 1,2,4-oxadiazoles as potential anticonvulsant agents. European Journal of Medicinal Chemistry, 112, 91-98. http://dx.doi.org/ 10.1016/j.ejmech.2016.01.054.
Moniot, S., Forgione, M., Lucidi, A., Hailu, G. S., Nebbioso, A., Carafa, V., Baratta, F., Altucci, L., Giacché, N., Passeri, D., Pellicciari, R., Mai, A., Steegborn, C., &Dante Rotili, D. (2017). Development of 1,2,4-oxadiazoles as potent and selective inhibitors of the human deacetylase sirtuin 2: structure-activity relationship, X-ray crystal structure, and anticancer activity, Journal of Medicinal Chemistry, 60(6), 2344-2360. http://dx.doi.org/10.1021/acs.jmedchem.6b01609.
Morales, G., Paredes, A., Sierra, P., &Loyola, L.A. (2008). Antimicrobial Activity of Three Baccharis Species Used in the Traditional Medicine of Northern Chile. Molecules, 13, 790-94. https://doi.org/10.3390/molecules13040790
Ölmez, N. A., & Waseer, F. (2020). New Potential Biologically Active Compounds: Synthesis and Characterization of Urea and Thiourea Derivativpes Bearing 1,2,4-oxadiazole Ring. Current organic synthesis, 17(7), 525-534. https://doi.org/10.2174/1570179417666200417112106
Parrino, B., Carbone, D., Cascioferro, S., Pecoraro, C., Giovannetti, E., Deng, D., Di Sarno, V., Musella, S., Auriemma, G., Cusimano, M. G., Schillaci, D., Cirrincione, G., & Diana, P. (2021). 1,2,4-Oxadiazole topsentin analogs as staphylococcal biofilm inhibitors targeting the bacterial transpeptidase sortase A. European journal of medicinal chemistry, 209, 112892. https://doi.org/10.1016/j.ejmech.2020.112892
Puzanov, A. I., Ryabukhin, D. S., Zalivatskaya, A. S., Zakusilo, D. N., Mikson, D. S., Boyarskaya, I. A., &Vasilyev, A. V. (2021). Synthesis of 5-arylacetylenyl-1,2,4-oxadiazoles and their transformations under superelectrophilic activation conditions. Beilstein Journal of Organic Chemistry. 17, 2417-2424. https://doi.org/10.3762/bjoc.17.158
Rodrigues, M. P., Tomaz, D. C., Ângelo de Souza, L., Onofre, T. S., Aquiles de Menezes, W., Almeida-Silva, J., Suarez-Fontes, A. M., Rogéria de Almeida, M., Manoel da Silva, A., &Bressan, G. C., André Nanner-Santos, M., Lopes Rangel Fietto, J. & Ricardo Teixeira, R. (2019). Synthesis of Cinnamic Acid Derivatives and Leishmanicidal Activity against Leishmania Braziliensis. European Journal of Medicinal Chemistry, 183, 111688. https://doi.org/10.1016/j.ejmech.2019.111688
Ruwizhi, N., &Aderibigbe, B. A. (2020). Cinnamic Acid Derivatives and Their Biological Efficacy. International Journal of Molecular Sciences, 21, E5712. DOI: 10.3390/ijms21165712
Sova, M. (2012). Antioxidant and antimicrobial activities of cinnamic acid derivatives. Mini reviews in medicinal chemistry, 12(8), 749-767. https://doi.org/10.2174/138955712801264792
Sortino, M., Cechinel Filho, V., Corrêa, R., &Zacchino, S. (2008). N-Phenyl and N-phenylalkyl-maleimides acting against Candida spp.: Time-to-kill, stability, interaction with maleamic acids. Bioorganic & Medicinal Chemistry Letters, 16, 560-568. https://doi.org 10.1016/j.bmc.2007.08.030
Srivastava, R. M., Pereira, M. C., Faustino, W. W. M., Coutinho, K., Anjos, J. V., &Melo, S. J (2009). Synthesis, mechanism of formation, and molecular orbital calculations of arylamidoximes. Monatshefte fuer Chemie/Chemical Monthly, 140(11), 1319-1324. DOI:10.1007/s00706-009-0186-7
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2022-01-31
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