Four new 1,3,4-bis-oxadiazole derivatives were synthesized, two of them bearing quaternary ammonium salts. The newly synthesized bis-1,3,4-oxadiazoles were investigated for their antibacterial activity against various Gram-positive and Gram-negative strains of bacteria. The target products were prepared from 2-(dimethylamino)ethyl methacrylate (DMAEMA) or 2-(diethylamino)ethyl methacrylate (DEAEMA) via reactions with hexanedioic acid. The structures of all synthesized compounds were confirmed by IR, 1H-NMR, and 13C-NMR spectroscopy. The results of biological activity testing showed that two compounds exhibited the best antibacterial activity against Citrobacterfreundii (ATCC 8090) and Methicillin-resistant Staphylococcus aureus (ATCC 43300) strains.
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A. Pace and P. Pierro, Org. Biomol. Chem., 7, 4337 – 4348 (2009).
K. Bethge, H. H. Pertz, and K. Rehse, Arch. Pharm., 338, 78 – 86 (2005).
D. K. Dalvie, A. S. Kalgutkar, S. C. Khojasteh-Bakht, et al., Chem. Res. Toxicol., 15, 269 – 299 (2002).
E. A. Ryzhova, A. G. Koryakova, E. A. Bulanova, et al., Pharm. Chem. J., 43, 148 – 153 (2009).
S. Balachandran, A. Rodge, P. K. Gadekar, et al., Bioorg. Med. Chem. Lett. , 19, 4773 – 4776 (2009).
J. Boström A. Hogner, A. Llinás, et al., J. Med. Chem., 55, 1817 – 1830 (2012).
A. C. L. Leite, R. F. Vieira, A. R. de Faria, et al., Il Farmaco, 55, 719 – 724(2000).
J. V. dos Anjos, D. Sinou, S. J. de Melo, and R. M. Srivastava, Carbohydr. Res., 342, 2440 – 2449 (2007).
J. Ziga, Current Org. Synth., 12, 1 – 6 (2015).
G. A. Allan, J. I. Gedge, A. N. Nedderman, et al., Xenobiotica , 36, 399 – 418 (2006).
J. G. Allen, M. J. Blackburn, and S. M. Caldwell, Xenobiotica , 1, 3 – 12 (1971).
J. Saunders, M. Cassidy, S. B. Freedman, et al., J. Med. Chem. , 33, 1128 – 1138 (1990).
K. P. Bateman, L. Trimble, N. Chauret, et al., J. Mass Spectrom., 41, 771 – 780 (2006).
A. Hall, S. H. Brown, A. Chowdhury, et al., Bioorg. Med. Chem. Lett. , 17, 4450 – 4455 (2007).
Y. Ducharme, M. Blouin, C. Brideau, et al., ACS Med. Chem. Lett., 1, 170 – 174 (2010).
F. Huguet, A. Melet, R. Alves de Sousa, et al., Chem. Med. Chem., 7 1020 – 1030 (2012).
R. S. Ferreira, C. Bryant, K. K. H. Ang, et al., J. Med. Chem., 52, 5005 – 5008 (2009).
F. Z. Dörwald: Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds, John Wiley & Sons: New York (2013), pp. 118 – 119.
Q. Xiaoshuai, L. Yancai, Z. Fang, et al., Appl. Surf. Sci., 328, 183 – 192 (2015).
G. Sauvet, S. Dupond, K. Kazmierski, and J. Chojnowski, J. Appl. Polym. Sci.. 75, 1005–1012 (2000).
G. A. Domagk, Deut. Med. Wochenschr., 61, 829 – 832 (1935).
G. L. Jeffrey, N. C. Peter, A. F. Preston, and H. W. James, React. Funct. Polym., 77, 39 – 46 (2014).
(a) Z. Anqiang, L. Qiongqiong, L. Yufeng, et al., React. Funct. Polym., 88, 39 – 46(2015); (b) W. Chamari, B. Marianna, B. Lívia, et al., Clin. Pharm., 4, 73 – 75 (2013).
T. Ulas and G. P. Spyros, Curr. Opin. Biotech., 33, 296 – 304 (2015).
N. Basillico, M. Migotto, D. P. Ilboudo, et al., Bioorg. Med. Chem., 23, 4681 – 4687 (2015).
L. Yaling, L. Qiongqiong; C. Liujun, et al., React. Funct. Polym., 85, 36 – 44 (2014).
Z. S. Xu, W. Ning, C. Di, et al., Chin. Chem. Lett., 22, 887 – 890 (2011).
R. B. Yashumati, P. Ashutosh, J. Vivek, and K. Dharma, Saudi Pharm. J., 22, 290 – 302 (2014).
H. Guo-Qiang, H. Li-Li, W. Guo-Qiang, et al., Acta Pharm. Sinica , 47, 1017 – 1022 (2012).
B. S. Furniss, A. J. Hannford, P. W. G. Smith, and A. R. Tatchell, in: Vogel’s Text Book of Practical Organic Chemistry. 5th Edition, John Wiley & Sons: New York (1989), p. 1076.
A. K. Behera, R. K. Behera, R. Pradhan, et al., Indian J. Heterocycl. Chem., 16, 167 – 170 (2006).
L. Guiqian, W. Dingcai, F. Ruowen, React. Funct. Polym., 67, 355 – 366 (2007).
M27-A2 Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts: Approved Standard, 2nd Edition, Clinical and Laboratory Standards Institute (United States), NCCLS Document, Vol. 22, No. 5 (2002).
S. O. Podunavac-Kuzmanovic, D. D. Cvetkovic, and D. J. Barna, J. Serb. Chem. Soc., 73 , 967 – 978 (2008).
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Prof. Dr. Taoufik Rohand thanks the University Cadi Ayyad and specially the Faculty Polidisciplinaire of Safi for the profesorship and the Laboratory of Analytical and Molecular Chemistry for financial support.
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Rohand, T., Ramli, Y., Baruah, M. et al. Synthesis, Structure Elucidation and Antimicrobial Properties of New Bis-1,3,4-Oxadiazole Derivatives. Pharm Chem J 53, 150–154 (2019). https://doi.org/10.1007/s11094-019-01969-2
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DOI: https://doi.org/10.1007/s11094-019-01969-2