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Synthesis and Biological Evaluation of 1,3,4-Oxadiazole Derivatives as Acetylcholinesterase Inhibitors

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Abstract

A series of 1,3,4-oxadiazole derivatives were designed, synthesized, and evaluated as acetylcholin­esterase inhibitors. Their structure was confirmed by IR, NMR, and high-resolution mass spectra. The syn­thesized compounds showed significant acetylcholinesterase inhibitory activity with an IC50 value of 0.07 μM for the most potent compound. Molecular docking study of the most active compound indicated that it interacted with the crucial amino acids present at the catalytic active site and peripheral anionic site of acetylcholinesterase. The results suggested that the obtained 1,3,4-oxadiazole derivatives may be the potential drug candidates for the treatment of Alzheimer’s disease as AChE inhibitors.

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REFERENCES

  1. De Bruijn, R.F. and Ikram, M.A., BMC Med., 2014, vol. 12, p. 130. https://doi.org/10.1186/s12916-014-0130-5

    Article  Google Scholar 

  2. Lasagna‐Reeves, C.A., Castillo‐Carranza, D.L., Sengupta, U., Sarmiento, J., Troncoso, J., Jackson, G.R., and Kayed, R., FASEB J., 2012, vol. 26, p. 1946. https://doi.org/10.1096/fj.11-199851

    Article  CAS  Google Scholar 

  3. Yang, S., Kaoru, Y., Shane, A.L., Scott, T.S., Zhao, Z., Luo, W., Richard, M.T., Salvatore, S., Lea, T., and Julio, C.R., Nature, 2017, vol. 549, p. 523. https://doi.org/10.1038/nature24016

    Article  CAS  Google Scholar 

  4. Choubey, P.K., Tripathi, A., Tripathi, M.K., Seth, A., and Shrivastava, S.K., Bioorg. Chem., 2021, vol. 111, article ID 104922. https://doi.org/10.1016/j.bioorg.2021.104922

  5. 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  Google Scholar 

  6. Lakshmithendral, K., Saravanan, K., Elancheran, R., Archana, K., Manikandan, N., Arjun, H.A., Ramana­than, M., Lokanath, N.K., and Kabilan, S., Eur. J. Med. Chem., 2019, vol. 168, p. 1. https://doi.org/10.1016/j.ejmech.2019.02.033

    Article  CAS  Google Scholar 

  7. Sekhar, M.M., Nagarjuna, U., Padmavathi, V., Padmaja, A., Reddy, N.V., and Vijaya, T., Eur. J. Med. Chem., 2018, vol. 145, p. 1. https://doi.org/10.1016/j.ejmech.2017.12.067

    Article  CAS  Google Scholar 

  8. Dewangan, D., Verma, V.S., Nakhate, L.T., Tripathi, D.K., Kashyap, P., and Dhongade, H., Med. Chem. Res., 2016, vol. 25, p. 2143. https://doi.org/10.1007/s00044-016-1641-8

    Article  CAS  Google Scholar 

  9. Chaves, J.D.S., Tunes, L.G., Franco, C.H.J., Francisco, T.M., Corrêa, C.C., and Silvane, M.F., Eur. J. Med. Chem., 2017, vol. 127, p. 727. https://doi.org/10.1016/j.ejmech.2016.10.052

    Article  CAS  Google Scholar 

  10. El-Sayed, W.A., El-Essawy, F.A., Ali, O.M., Nasr, B.S., Abdalla, M.M., and Abdel-Rahman, A.A.-H., Z. Natur­forsch., Teil C, 2009, vol. 64, p. 773. https://doi.org/10.1515/znc-2009-11-1203

    Article  CAS  Google Scholar 

  11. Mochona, B., Mazzio, E., Gangapurum, M., Mateeva, N., and Redda, K., Chem. Sci. Trans., 2015, vol. 4, p. 534. https://doi.org/10.7598/cst2015.1029

    Article  CAS  Google Scholar 

  12. Ahmed, K, Shaik, A.B., Reddy, G.N, Kumar, C.G., Joseph, J., Kumar, G.B., Purushotham, U., and Sastry, G.N., Med. Chem. Res., 2014, vol. 23, p. 2080. https://doi.org/10.1007/s00044-013-0786-y

    Article  CAS  Google Scholar 

  13. Mei, W.-W., Ji, Sh.-Sh., Xiao, W., Wang, X.-D., Jiang, Ch.-Sh., Ma, W.-Q., Zhang, H.-Y., Gong, J.-X., and Guo, Y.-W., Monatsh. Chem., 2017, vol. 148, p. 1807. https://doi.org/10.1007/s00706-017-1993-x

    Article  CAS  Google Scholar 

  14. Tripathi, A., Choubey, P.K., Sharma, P., Seth, A., Tripathi, P.N., Tripathi, M.K., Prajapati, S.K., Krishnamurthy, S., and Shrivastava, S.K., Eur. J. Med. Chem., 2019, vol. 183, article ID 111707. https://doi.org/10.1016/j.ejmech.2019.111707

  15. 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 

  16. Wang, S., Qi, L., Liu, H., Lei, K., and Liu, R., RSC Adv., 2020, vol. 10, p. 30848. https://doi.org/10.1039/D0RA05886F

    Article  CAS  Google Scholar 

  17. 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 

  18. Ellman, G., Courtney, K.D., Andres Jr, V., and Feather­stone, R.M., Biochem. Pharmacol., 1961, vol. 7, p. 88. https://doi.org/10.1016/0006-2952(61)90145-9

    Article  CAS  Google Scholar 

  19. Song, M.Q., Min, W., Wang, J., Si, X.X., Wang, X.J., Liu, Y.W., and Shi, D.H., J. Mol. Struct., 2021, vol. 1229, article ID 129784. https://doi.org/10.1016/j.molstruc.2020.129784

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Funding

The authors gratefully acknowledge financial supports of Graduate Research and Innovation Projects of Jiangsu Province (KYCX20-2895), Natural Science Foundation of Jiangsu Province (BK20191470), and project funded by the Priority Academic Program Development of Jiangsu higher education institutions.

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Authors and Affiliations

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

    Shun Yang, Jing-Pei Zou, Xiang-Rong Li, Rui Li, Jing-Jing Qian, Wen-Long Wu, Jia-Bin Su, Ke-Qi Chen, Tian Qin, Shan-Ming Liu, Wei-Wei Liu & Da-Hua Shi

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

    Shun Yang, Jing-Pei Zou, Xiang-Rong Li, Rui Li, Jing-Jing Qian, Wen-Long Wu, Jia-Bin Su, Ke-Qi Chen, Tian Qin, Shan-Ming Liu, Wei-Wei Liu & Da-Hua Shi

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

    Wei-Wei Liu & Da-Hua Shi

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  1. Shun Yang
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Correspondence to Da-Hua Shi.

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Yang, S., Zou, JP., Li, XR. et al. Synthesis and Biological Evaluation of 1,3,4-Oxadiazole Derivatives as Acetylcholinesterase Inhibitors. Russ J Org Chem 58, 1520–1526 (2022). https://doi.org/10.1134/S1070428022100207

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