Solid phase synthesis of novel 1,3,4-oxadiazole derivatives and evaluation of their antimicrobial activity

ABSTRACT A series of 5-(N-Aryl/Arylalkyl)-2-(3-Chclorophenyl)-1,3,4-oxadiazole have been synthesized. The constitution of the products has been delineated by elemental analysis and spectral analyses. All the synthesized compounds were screened for their antibacterial activity against Staphylococcus aureus MTCC-96, Escherichia coli MTCC-443, B. subtilis MTCC-441, P. aeruginosa MTCC-1688, and antifungal activity against Aspergillus niger MTCC-282 and Penicillium SP. at different concentration and compared with standards drugs. The minimum inhibition concentration (MIC) of the compounds was studied by micro broth dilution method. References Ainswarth, J. Am. Chem. Soc., 87(24), 5800-5801 (1965). https://doi.org/10.1021/ja00952a056 Kumar, A., D’Souza, S. S., Nagaraj, S. R. M., Gaonkar, S. L., Salimath, B. P., & Rai, K. L. (2009). 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C., Purohit, V. B., Avalani, J. R., Sapariya, N. H., & Raval, D. K. (2016). Design, synthesis, and characterization of a fluoro substituted novel pyrazole nucleus clubbed with 1, 3, 4-oxadiazole scaffolds and their biological applications. RSC Advances , 6(47), 41532-41541. https://doi.org/10.1039/c6ra01349j Rane, R. A., Bangalore, P., Borhade, S. D., & Khandare, P. K. (2013). Synthesis and evaluation of novel 4-nitropyrrole-based 1,3,4-oxadiazole derivatives as antimicrobial and anti-tubercular agents. European Journal of Medicinal Chemistry , 70, 49-58. https://doi.org/10.1016/j.ejmech.2013.09.039 Farghaly, A. H. (2004). Synthesis, Reactions and Antimicrobial Activity of Some New Indolyl‐1, 3, 4‐Oxadiazole, Thiazole and Pyrazole Derivatives. Journal of the Chinese Chemical Society , 51(1), 147-156. https://doi.org/10.1002/jccs.200400023 Desai, N. C., Bhatt, N. B., Somani, H. C., & Bhatt, K. A. (2016). Synthesis and antimicrobial activity of some thiazole and 1, 3, 4-oxadiazole hybrid heterocycles. Indian Journal of Chemistry , 55, 94-101. https://doi.org/10.1007/s00044-014-1108-8 Sangshetti, J. N., Chabukswar, A. R., & Shinde, D. B. (2011). Microwave assisted one pot synthesis of some novel 2, 5-disubstituted 1, 3, 4-oxadiazoles as antifungal agents. Bioorganic & medicinal chemistry letters , 21(1), 444- 448. https://doi.org/10.1016/j.bmcl.2010.10.120 Terenzi, A., Fanelli, M., Ambrosi, G., Amatori, S., Fusi, V., Giorgi, L & Barone, G. (2012). DNA binding and antiproliferative activity toward human carcinoma cells of copper (II) and zinc (II) complexes of a 2, 5-diphenyl [1, 3, 4] oxadiazole derivative. Dalton Transactions , 41(15), 4389-4395. https://doi.org/10.1039/c2dt11759b Bhat, K. S., Karthikeyan, M. S., Holla, B. S., & Shetty, N. S. (2004). Synthesis of some new fluorine containing 1, 3, 4-oxadiazole derivatives as potential antibacterial and anticancer agents. Indian J Chem B , 43, 1765-1769. https://doi.org/10.1002/chin.200450090 Abdel-Aziz, M., A Metwally, K., Gamal-Eldeen, A. M., & M Aly, O. (2016). 1, 3, 4-oxadiazole-2-thione Derivatives; Novel Approach for Anticancer and Tubulin Polymerization Inhibitory Activities. Anti-Cancer Agents in Medicinal Chemistry (Formerly Current Medicinal Chemistry-Anti-Cancer Agents) , 16(2), 269-277. https://doi.org/10.2174/1871520615666150907093855 Khan, M. T. H., Choudhary, M. I., Khan, K. M., & Rani, M. (2005). Structure–activity relationships of tyrosinase inhibitory combinatorial library of 2, 5-disubstituted-1, 3, 4-oxadiazole analogues. Bioorganic & Medicinal Chemistry , 13(10), 3385-3395. https://doi.org/10.1016/j.bmc.2005.03.012 Dolman, S. J., Gosselin, F., O'Shea, P. D., & Davies, I. W. (2006). Superior reactivity of thiosemicarbazides in the synthesis of 2-amino-1, 3, 4-oxadiazoles. The Journal of Organic Chemistry , 71(25), 9548-9551. https://doi.org/10.1021/jo0618730 El‐Samii, Z. K. (1992). Synthesis and anti‐inflammatory activity of some novel 1,3,4‐oxadiazole derivatives. Journal of Chemical Technology and Biotechnology , 53(2), 143-146. https://doi.org/10.1002/jctb.280530206 Ilango, K., Valentina, P., Kumar, G., Dixit, D., Nilewar, S., & K Kathiravan, M. (2015). Design, Synthesis and QSAR Studies on a Series of 2, 5- Disubstituted-1, 3, 4-oxadiazole Derivatives of Diclofenac and Naproxen for Analgesic and Anti-inflammatory Activity. Medicinal Chemistry , 11(8), 753-763. https://doi.org/10.2174/1573406411666150519112037 Akhter, M., Husain, A., Azad, B., & Ajmal, M. (2009). Aroylpropionic acid based 2, 5-disubstituted-1, 3, 4-oxadiazoles: Synthesis and their anti-inflammatory and analgesic activities. European Journal of Medicinal Chemistry , 44(6), 2372-2378. https://doi.org/10.1016/j.ejmech.2008.09.005 Johns, B. A., Weatherhead, J. G., Allen, S. H., Thompson, J. B., Garvey, E. P., Foster, S. A., ... & Miller, W. H. (2009). 1, 3, 4-Oxadiazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 2: SAR of the C5 position. Bioorganic & Medicinal Chemistry Letters , 19(6), 1807-1810. https://doi.org/10.1016/j.bmcl.2009.01.089 Khatale, P. N., & Sivakumar, T. (2015). Methods of Synthesis of 1,3,4‐Oxadiazole‐2‐thiones: A Review. ChemInform , 46(13). https://doi.org/10.1002/chin.201513324 Khalilullah, H., J Ahsan, M., Hedaitullah, M., Khan, S., & Ahmed, B. (2012). 1,3,4-Oxadiazole: A biologically active scaffold. Mini reviews in medicinal chemistry , 12(8), 789-801. https://doi.org/10.2174/138955712801264800 Parikh, K., & Joshi, D. (2014). Synthesis and evaluation of 2-(5-(aryl)-1,3,4-oxadiazol-2-ylthio)-N-(3-(trifluoromethyl) phenyl) acetamides and N-(4- chloro-3-fluorophenyl)-2-(5-(aryl)-1, 3, 4-oxadiazol-2-ylthio) acetamides as antimicrobial agents. Journal of Chemical Sciences , 126(3), 827-835. https://doi.org/10.1007/s12039-014-0625-9 Hajdok, I., Bona, A., Werner, H. J., & Kerres, J. (2014). Synthesis and characterization of fluorinated and sulfonated poly (arylene ether-1, 3, 4- oxadiazole) derivatives and their blend membranes. European Polymer Journal , 52, 76-87. https://doi.org/10.1016/j.eurpolymj.2013.12.003 National committee for clinical laboratory standards. (M7A5), 5th ed.; NCCLS: Wayne, PA, (2000). https://doi.org/10.1093/clinchem/34.8.1665 Patel, N.B.; Shaikh, A.R. Indian J. Chem. 49B, 929-936 (2010). https://doi.org/10.4103/0970-0218.62571 Rattan, A. Antimicrobial in laboratory medicine; BI Churchill Livingstone: India, p. 85, (2000). https://doi.org/10.1111/j.1365-2257.1985.tb00041.x Download all article in PDF WSN 147 (2020) 35-44

Solid phase synthesis of novel 1,3,4-oxadiazole derivatives and evaluation of their antimicrobial activity

Authors: Shobhana A. Gadara, Kartik D. Ladva, 147 (2020) 35-44

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Solid phase synthesis of novel 1,3,4-oxadiazole derivatives and evaluation of their antimicrobial activity

Authors: Shobhana A. Gadara, Kartik D. Ladva, 147 (2020) 35-44

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