Wed, Apr 24, 2024
Volume 15, Issue 5 (Sep-Oct 2021)
mljgoums 2021, 15(5): 13-18 |
Back to browse issues page
Download citation:
BibTeX | RIS | EndNote | Medlars | ProCite | Reference Manager | RefWorks
Send citation to:
BibTeX | RIS | EndNote | Medlars | ProCite | Reference Manager | RefWorks
Send citation to:
Zarrabi Ahrabi N, souldozi A, SarveAhrabi Y. Synthesis of New Three-Component Derivatives of 1, 3, 4-Oxadiazole and Evaluation of Their In Vitro Antibacterial and Antifungal Properties. mljgoums 2021; 15 (5) :13-18
URL: http://mlj.goums.ac.ir/article-1-1308-en.html
URL: http://mlj.goums.ac.ir/article-1-1308-en.html
1- Department of Biology, Central Tehran Branch, Islamic Azad University, Tehran, Iran
2- Department of Chemistry, Urmia Branch, Islamic Azad University, Urmia, Iran
3- Department of Biology, Central Tehran Branch, Islamic Azad University, Tehran, Iran , yasin.ahrabi2016@gmail.com
2- Department of Chemistry, Urmia Branch, Islamic Azad University, Urmia, Iran
3- Department of Biology, Central Tehran Branch, Islamic Azad University, Tehran, Iran , yasin.ahrabi2016@gmail.com
Abstract: (3229 Views)
Background and objectives: Antibiotic resistance is a major public health challenge. The pervasive antibiotic misuse can lead to increased antibiotic resistance. Thus, there is a need for discovery of new compounds against drug-resistant microorganisms. We synthesized new series of 1, 3, 4-oxadiazole derivatives (4a-4d) and evaluated the antibacterial and antifungal activity of the derivatives against Staphylococcus aureus, Staphylococcus epidermidis, Acinetobacter baumannii, Klebsiella pneumoniae, Aspergillus fumigatus and Aspergillus flavus.
Methods: The new derivatives of 1, 3, 4-oxadiazole were synthesized using a single-stage, high-yield method. The structure of the new compounds was confirmed by infrared spectroscopy, carbon-nuclear magnetic resonance and hydrogen- nuclear magnetic resonance. Then, antibacterial and antifungal activities of the prepared derivatives (1 mg/ml) were evaluated by determining minimum inhibitory concentration and minimum bactericidal/fungicidal concentration using the agar well diffusion method.
Results: All synthesized compounds, especially (4d) with methoxyphenyl group, exhibited powerful antibacterial activity against the tested bacteria. However, the compounds had no antifungal effect.
Conclusion: Our findings indicate the antibacterial potential of the novel synthetic 1, 3, 4-oxadiazole compounds.
Methods: The new derivatives of 1, 3, 4-oxadiazole were synthesized using a single-stage, high-yield method. The structure of the new compounds was confirmed by infrared spectroscopy, carbon-nuclear magnetic resonance and hydrogen- nuclear magnetic resonance. Then, antibacterial and antifungal activities of the prepared derivatives (1 mg/ml) were evaluated by determining minimum inhibitory concentration and minimum bactericidal/fungicidal concentration using the agar well diffusion method.
Results: All synthesized compounds, especially (4d) with methoxyphenyl group, exhibited powerful antibacterial activity against the tested bacteria. However, the compounds had no antifungal effect.
Conclusion: Our findings indicate the antibacterial potential of the novel synthetic 1, 3, 4-oxadiazole compounds.
Research Article: Original Paper |
Subject:
Microbiology
Received: 2020/08/3 | Accepted: 2021/05/22 | Published: 2021/08/31 | ePublished: 2021/08/31
Received: 2020/08/3 | Accepted: 2021/05/22 | Published: 2021/08/31 | ePublished: 2021/08/31
References
1. Singh N, Yeh PJ. Suppressive drug combinations and their potential to combat antibiotic resistance. The Journal of antibiotics. 2017; 70(11): 1033-42. [View at Publisher] [DOI:10.1038/ja.2017.102] [PubMed] [Google Scholar]
2. Alshon A, Almiahi Y. Client's Attitude Regarding Antibiotics Misuse in Primary Health Care Centers. Indian Journal of Forensic Medicine & Toxicology. 2020; 14(2): 1009-11. [View at Publisher] [PubMed]
3. Jensen CS, Nielsen SB, Fynbo L. Concluding Remarks on 'Risking Antimicrobial Resistance'. Risking Antimicrobial Resistance: Springer. 2019; 199-208. [View at Publisher] [DOI:10.1007/978-3-319-90656-0_12] [Google Scholar]
4. Hellewell L, Bhakta S. Chalcones, stilbenes and ketones have anti-infective properties via inhibition of bacterial drug-efflux and consequential synergism with antimicrobial agents. Access Microbiology. 2020;2(4):e000105. [View at Publisher] [DOI:10.1099/acmi.0.000105] [PubMed] [Google Scholar]
5. Hover BM, Kim S-H, Katz M, Charlop-Powers Z, Owen JG, Ternei MA, et al. Culture-independent discovery of the malacidins as calcium-dependent antibiotics with activity against multidrug-resistant Gram-positive pathogens. Nature microbiology. 2018; 3(4): 415-22. [View at Publisher] [DOI:10.1038/s41564-018-0110-1] [PubMed] [Google Scholar]
6. Shrivastava SR, Shrivastava PS, Ramasamy J. World health organization releases global priority list of antibiotic-resistant bacteria to guide research, discovery, and development of new antibiotics. Journal of Medical Society. 2018; 32(1): 76. [DOI:10.4103/jms.jms_25_17] [Google Scholar]
7. Leonardelli F, Macedo D, Dudiuk C, Cabeza MS, Gamarra S, Garcia-Effron G. Aspergillus fumigatus intrinsic fluconazole resistance is due to the naturally occurring T301I substitution in Cyp51Ap. Antimicrobial agents and chemotherapy. 2016; 60(9): 5420-6. [View at Publisher] [DOI:10.1128/AAC.00905-16] [PubMed] [Google Scholar]
8. Boström J, Hogner A, Llinàs A, Wellner E, Plowright AT. Oxadiazoles in medicinal chemistry. Journal of medicinal chemistry. 2012; 55(5): 1817-30. [View at Publisher] [DOI:10.1021/jm2013248] [PubMed] [Google Scholar]
9. Pibiri I, Lentini L, Melfi R, Tutone M, Baldassano S, Galluzzo PR, et al. Rescuing the CFTR protein function: Introducing 1, 3, 4-oxadiazoles as translational readthrough inducing drugs. European journal of medicinal chemistry. 2018; 159: 126-42. [View at Publisher] [DOI:10.1016/j.ejmech.2018.09.057] [PubMed] [Google Scholar]
10. Sarveahrabi Y, Souldozi A, Talebi R. 2-Substituent Synthesis of 5-3-Methoxyphenyl and 5-4-Methoxyphenyl-1, 3, 4-Oxadiazoles, 2-Yl-Pyridine-2-Yl-Methanol in Positions of 2 and 3 of 1, 3, 4-Oxadiazoles Containing Halogen and the Evaluation of Their Antibacterial Properties. Navid No. 2020; 22(72): 1-13. [View at Publisher] [Google Scholar]
11. Capoci IRG, Sakita KM, Faria DR, Rodrigues Vendramini FAV, Arita GS, de Oliveira AG, et al. Two new 1, 3, 4-oxadiazoles with effective antifungal activity against Candida albicans. Frontiers in microbiology. 2019; 10: 2130. [View at Publisher] [DOI:10.3389/fmicb.2019.02130] [PubMed] [Google Scholar]
12. Patel RV, Kumari P, Chikhalia KH. New quinolinyl-1,3,4-oxadiazoles: synthesis, in vitro antibacterial, antifungal and antituberculosis studies. Med Chem. 2013 1;9(4):596-607. [View at Publisher] [DOI:10.1002/slct.201802227] [PubMed] [Google Scholar]
13. Albratty M, El-Sharkawy KA, Alhazmi HA. Synthesis and evaluation of some new 1, 3, 4-oxadiazoles bearing thiophene, thiazole, coumarin, pyridine and pyridazine derivatives as antiviral agents. Acta Pharmaceutica. 2019; 69(2): 261-76. [View at Publisher] [DOI:10.2478/acph-2019-0015] [PubMed] [Google Scholar]
14. Caneschi W, Enes KB, Carvalho de Mendonça C, de Souza Fernandes F, Miguel FB, da Silva Martins J, et al. Synthesis and anticancer evaluation of new lipophilic 1,2,4 and 1,3,4-oxadiazoles. Eur J Med Chem. 2019 1;165:18-30 [View at Publisher] [DOI:10.1016/j.ejmech.2019.01.001] [PubMed] [Google Scholar]
15. Thakkar SS, Thakor P, Doshi H, Ray A. 1,2,4-Triazole and 1,3,4-oxadiazole analogues: Synthesis, MO studies, in silico molecular docking studies, antimalarial as DHFR inhibitor and antimicrobial activities. Bioorg Med Chem. 2017 1;25(15):4064-4075. [View at Publisher] [DOI:10.1016/j.bmc.2017.05.054] [PubMed] [Google Scholar]
16. Rennie R, Turnbull L, Brosnikoff C, Cloke J. First comprehensive evaluation of the MIC evaluator device compared to Etest and CLSI reference dilution methods for antimicrobial susceptibility testing of clinical strains of anaerobes and other fastidious bacterial species. Journal of Clinical Microbiology. 2012; 50(4): 1153-7. [View at Publisher] [DOI:10.1128/JCM.05397-11] [PubMed] [Google Scholar]
17. Othman AA, Kihel M, Amara S. 1, 3, 4-Oxadiazole, 1, 3, 4-thiadiazole and 1, 2, 4-triazole derivatives as potential antibacterial agents. Arabian Journal of Chemistry. 2019; 12(7): 1660-75. [View at Publisher] [DOI:10.1016/j.arabjc.2014.09.003] [Google Scholar]
18. Aghekyan А, Mkryan G, Panosyan H, Safaryan A, Stepanyan H. Synthesis and Antibacterial Activity of Novel (4-Methoxyphenyl)-tetrahydropyranyl-substituted 1, 3, 4-Oxadiazoles. Russian Journal of Organic Chemistry. 2020; 56: 281-6. [View at Publisher] [DOI:10.1134/S1070428020020177] [PubMed] [Google Scholar]
19. Guo Y, Xu T, Bao C, Liu Z, Fan J, Yang R, Qin S. Design and synthesis of new norfloxacin-1,3,4-oxadiazole hybrids as antibacterial agents against methicillin-resistant Staphylococcus aureus (MRSA). Eur J Pharm Sci. 2019 1;136:104966. [View at Publisher] [DOI:10.1016/j.ejps.2019.104966] [PubMed] [Google Scholar]
20. Tresse C, Radigue R, Gomes Von Borowski R, Thepaut M, Hanh Le H, Demay F, Georgeault S, Dhalluin A, Trautwetter A, Ermel G, Blanco C, van de Weghe P, Jean M, Giard JC, Gillet R. Synthesis and evaluation of 1,3,4-oxadiazole derivatives for development as broad-spectrum antibiotics. Bioorg Med Chem. 2019 1;27(21):115097. [View at Publisher] [DOI:10.1016/j.bmc.2019.115097] [PubMed] [Google Scholar]
21. SarveAhrabi Y, Souldozi A, Zarrabi Ahrabi N. In Vitro Evaluation of Antimicrobial Properties of Some New 1, 3, 4-Oxadiazole Derivatives against Acinetobacter baumannii. Infection Epidemiology and Microbiology. 2020; 6(1): 37-49. [DOI:10.29252/iem.6.1.37] [Google Scholar]
Send email to the article author
| Rights and permissions | |
 |
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License. |
Enamad
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.