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Design, Synthesis, and Biological Evaluation of 1,3,4-Oxadiazole Derivatives

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Abstract

A series of 1,3,4-oxadiazole derivatives were synthesized starting from substituted phenylacetic acids, and their structures were confirmed by IR, NMR, and HRMS data. The synthesized compounds showed potent in vitro cholinesterase inhibitory activities with IC50 values of 8.59 μM against butyrylcholinesterase (6a) and 7.12 μM against acetylcholinesterase (6f). Molecular docking studies indicated that compound 6f could interact with the peripheral anion that binds to acetylcholinesterase. Moreover, compound 6c also exhibited strong anti-inflammatory effect. This compound could significantly reduce LPS-induced secretion of inflam­matory cytokines IL-6, IL-1β, and TNF-α in RAW 264.7 cells. These results suggested that 1,3,4-oxadiazole derivatives may be promising lead compounds for the treatment of Alzheimer’s disease.

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REFERENCES

  1. Yan, B., Li, Y., Li, L., Yang, X., Li, T.Q., Yang, G., and Jiang, M., Comput. Biol. Med., 2022, vol. 148, article ID 105944. https://doi.org/10.1016/j.compbiomed.2022.105944

  2. Ferreira-Vieira, T.H., Guimaraes, I.M., Silva, F.R., and Ribeiro, F.M., Curr. Neuropharmacol., 2016, vol. 14, p. 101. https://doi.org/10.2174/1570159X13666150716165726

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Calzaferri, F., Narros-Fernandez, P., de Pascual, R., de Diego, A.M.G., Nicke, A., Egea, J., Garcia, A.G., and de los Rios, C., J. Med. Chem., 2021, vol. 64, p. 2272. https://doi.org/10.1021/acs.jmedchem.0c02145

    Article  CAS  PubMed  Google Scholar 

  4. Tramutola, A., Lanzillotta, C., Perluigi, M., and Butterfield, D.A., Brain. Res. Bull., 2017, vol. 133, p. 88. https://doi.org/10.1016/j.brainresbull.2016.06.005

    Article  CAS  PubMed  Google Scholar 

  5. Muralidar, S., Ambi, S.V., Sekaran, S., Thirumalai, D., and Palaniappan, B., Int. J. Biol. Macromol., 2020, vol. 163, p. 1599. https://doi.org/10.1016/j.ijbiomac.2020.07.327

    Article  CAS  PubMed  Google Scholar 

  6. Wu, Y., Su, X., Lu, J., Wu, M., Yang, S.Y., Mai, Y., Deng, W., and Xue, Y., Front. Pharmacol., 2022, vol. 13, article ID 905708. https://doi.org/10.3389/fphar.2022.905708

  7. Parri, H.R., Hernandez, C.M., and Dineley, K.T., Biochem. Pharmacol., 2011, vol. 82, p. 931. https://doi.org/10.1016/j.bcp.2011.06.039

    Article  CAS  PubMed  Google Scholar 

  8. Jia, J.P., Jia, J.M., Zhou, W.D., Xu, M., Chu, C.B., and Yan, X., Chin. Med. J., Engl. Ed., 2004, vol. 117, p. 1161. https://doi.org/10.3760/cma.j.issn.0366-6999.2004

    Article  CAS  Google Scholar 

  9. Singh, A. and Jha, A., J. Pharm. Res. Int., 2021, vol. 33, p. 121. https://doi.org/10.9734/JPRI/2021/V33I60A34463

    Article  Google Scholar 

  10. Mesulam, M., Learn. Mem., 2004, vol. 11, p. 43. https://doi.org/10.1101/lm.69204

    Article  PubMed  Google Scholar 

  11. Malinski, T., J. Alzheimerʼs Dis., 2007, vol. 11, p. 207. https://doi.org/10.3233/jad-2007-11208

    Article  CAS  PubMed  Google Scholar 

  12. Jones, J.H., Xin, Z., Himmelbauer, M., Dechants­reiter, M., Enyedy, I., Hedde, J., Fang, T., Coomara­swamy, J., King, K.W., Murugan, P., Santoro, J.C., Hesson, T., Walther, D.M., Wei, R., Zheng, F., Marcotte, D.J., Spilker, K., Kumar, P.R., Liu, Y., Gilfillan, R., and Turiso, F.G.L., J. Med. Chem., 2021, vol. 64, p. 15402. https://doi.org/10.1021/acs.jmedchem.1c01458

    Article  CAS  PubMed  Google Scholar 

  13. Wong, C.H., Gan, S.Y., Tan, S.C., Gany, S.A., Ying, T., Gray, A.I., Igoli, J., Chan, E.W.L., and Phang, S.M., J. Appl. Phycol., 2018, vol. 30, p. 3261. https://doi.org/10.1007/s10811-018-1495-1

    Article  CAS  Google Scholar 

  14. Piyoosh, S., Avanish, T., Nath, T.P., Sen, S.S., Pratap, S.S., and Kumar, S.S., ACS Chem. Neurosci., 2019, vol. 10, p. 4361. https://doi.org/10.1021/acschemneuro.9b00430

    Article  CAS  Google Scholar 

  15. Sun, Y., Yang, Z.H., and Gu, W., Chin. J. Struct. Chem., 2022, vol. 41, p. 98. https://doi.org/10.14102/j.cnki.0254-5861.2011-3232

    Article  CAS  Google Scholar 

  16. Vanjare, B.D., Choi, N.G., Seok, Y., Raza, E., Hassan, M., Lee, K.H., and Kim, S.J., Mol. Diversity, 2022, vol. 27, p. 193. https://doi.org/10.1007/S11030-022-10416-6

    Article  Google Scholar 

  17. Karabelyov, V., Kondeva-Burdina, M., and Angelo­va, V.T., Bioorg. Med. Chem., 2021, vol. 29, article ID 115888. https://doi.org/10.1016/J.BMC.2020.115888

  18. Bansal, S., Bala, M., Suthar, S.K., Choudhary, S., Bhattacharya, S., Bhardwaj, V., Singla, S., and Joseph, A., Eur. J. Med. Chem., 2014, vol. 80, p. 167. https://doi.org/10.1016/j.ejmech.2014.04.045

    Article  CAS  PubMed  Google Scholar 

  19. Yang, S., Zou, J.P., Li, X.R., Li, R., Qian, J.J., Wu, W.L., Su, J.B., Chen, K.Q., Qin, T., Liu, S.M., Liu, W.W., and Shi, D.H., Russ. J. Org. Chem., 2022, vol. 58, p. 1520. https://doi.org/10.1134/S1070428022100207

    Article  CAS  Google Scholar 

  20. Luo, L., Li, Y., Qiang, X., Cao, Z., Xu, R., Yang, X., Xiao, G., Song, Q., Tan, Z., and Deng, Y., Bioorg. Med. Chem., 2017, vol. 25, p. 1997. https://doi.org/10.1016/j.bmc.2017.02.027

    Article  CAS  PubMed  Google Scholar 

  21. Lu, C.L., Zhu, W., Wang, M., Hu, M.M., Chen, W.L., Xu, X.J., and Lu, C.J., Carbohydr. Polym., 2015, vol. 122, p. 428. https://doi.org/10.1016/j.carbpol.2014.11.035

    Article  CAS  PubMed  Google Scholar 

  22. Xie, C.H., Kang, J., Li, Z.M., Schauss, A.G., Badger, T.M., Nagarajan, S., Wu, T., Wu, X.L., J. Nutr. Biochem., 2012, vol. 23, p. 1184. https://doi.org/10.1016/j.jnutbio.2011.06.013

    Article  CAS  PubMed  Google Scholar 

  23. Banday, M.R., Mattoo, R.H., and Rauf, A., J. Chem. Sci., 2010, vol. 122, p. 177. https://doi.org/10.1007/s12039-010-0019-6

    Article  CAS  Google Scholar 

  24. Wang, S., Qi, L., Liu, H., Lei, K., Wang, X., and Liu, R., RSC Adv., 2020, vol. 10, p. 30848. https://doi.org/10.1039/d0ra05886f

    Article  CAS  PubMed  PubMed Central  ADS  Google Scholar 

  25. Shi, J., Luo, N., Ding, M., and Bao, X., Chin. Chem. Lett., 2020, vol. 31, p. 434. https://doi.org/10.1016/j.cclet.2019.06.037

    Article  CAS  Google Scholar 

  26. Shi, D.H., Huang, W., Li, C., Liu, Y.W., and Wang, S.F., Eur. J. Med. Chem., 2014, vol. 75, p. 289. https://doi.org/10.1016/j.ejmech.2014.01.058

    Article  CAS  PubMed  Google Scholar 

  27. Ma, F.W., Liu, H.B., Xu, S., Cheng, Y.Y., Fei, Q, and Chen, H.J., Int. J. Biol. Macromol., 2021, vol. 171, p. 177. https://doi.org/10.1016/J.IJBIOMAC.2021.01.009

    Article  CAS  PubMed  Google Scholar 

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Funding

The authors thank the Jiangsu Graduate Research Innovation Program (KYCX2021_078) and Jiangsu Provincial Key Discipline Development Project for financial support of this work.

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Authors and Affiliations

  1. Jiangsu Key Laboratory of Marine Biotechnology, Jiangsu Ocean University/Jiangsu Key Laboratory of Marine Bioresources and environment, Jiangsu Ocean University, 222005, Lianyungang, China

    Shan-Ming Liu, Wei Zhang, Shun Yang, Jing-Pei Zou, Jing-Jing Qian, Rui Li, Jing-Quan Dong & Da-Hua Shi

  2. School of Pharmacy, Jiangsu Ocean University, 222005, Lianyungang, China

    Shan-Ming Liu, Wei Zhang, Shun Yang, Jing-Pei Zou, Jing-Jing Qian, Rui Li, Wei-Wei Liu, Jing-Quan Dong & Da-Hua Shi

  3. Co-Innovation Center of Jiangsu Marine Bio-industry Technology, 222005, Lianyungang, China

    Wei-Wei Liu & Da-Hua Shi

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  1. Shan-Ming Liu
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Liu, SM., Zhang, W., Yang, S. et al. Design, Synthesis, and Biological Evaluation of 1,3,4-Oxadiazole Derivatives. Russ J Org Chem 59, 2214–2220 (2023). https://doi.org/10.1134/S1070428023120205

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