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Synthesis of Some Benzimidazole-Thiophene Hybrids as Potential Urease and Lipase Inhibitors

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Abstract

In this study, some benzimidazole-thiophene hybrid compounds containing isatin and salicyl moieties were synthesized and investigated for their urease and lipase inhibition properties. Most of the synthesized compounds were found to show effective antiurease activities, when compared with standard Thiourea (0.5027 ± 0.0293 µM). The synthesized isatin containing hybrids (IVa–IVc) showed antiurease inhibitory activities ranging from 0.411 ± 0.0337 to 0.431 ± 0.0446 µM, while IC50 of standard thiourea was 0.5027 ± 0.0293 µM. The general of salicyl containing hybrids showed low antiurease inhibitory activities, while compound (Ve) showed 0.338 ± 0.0387 µM activity. The lipase inhibition activities of the synthesized hybrid molecules showed the activities ranging from 0.287 ± 0.0341 to 0.912 ± 0.0832 µM, while the standard Orlistat showed 0.21 ± 0.012 µM activity. In the light of the information obtained from this study, the results showed that the synthesized hybrid compounds could be potential antilipase and antiurease agents.

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REFERENCES

  1. Jin, D., Zhao, S., Zheng, N., Bu, D., Beckers, Y., Denman, S.E., McSweeney, C.S., and Wang, J., Front. Microbiol., 2017, vol. 8, pp. 1–10. https://doi.org/10.3389/fmicb.2017.00385

    Article  Google Scholar 

  2. Biglar, M., Mirzazadeh, R., Asadi, M., Sepehri, S., Valizadeh, Y., Sarrafi, Y., Amanlou, M., Larijani, B., Mohammadi-Khanaposhtani, M., and Mahdavi, M., Bioorg. Chem., 2020, vol. 95, pp. 1–7. https://doi.org/10.1016/j.bioorg.2019.103529

    Article  CAS  Google Scholar 

  3. Azizian, H., Nabati, F., Sharifi, A., Siavoshi, F., Mahdavi, M., and Amanlou, M. J., Mol. Model., 2012, vol. 18, pp. 2917–2927. https://doi.org/10.1007/s00894-011-1310-2

    Article  CAS  PubMed  Google Scholar 

  4. Sadat-Ebrahimi, S.E., Bigdelou, A., Sooreshjani, R.H., Montazer, M.N., Zomorodian, K., Irajie, C., Yahya-Meymandi, A., Biglar, M., Larijani, B., Amanlou, M., Iraji, A., and Mahdavi, M., J. Mol. Struct., 2022, vol. 1263, pp. 1–9. https://doi.org/10.1016/j.molstruc.2022.133078

    Article  CAS  Google Scholar 

  5. Abid, O.-U.-R., Babar, T.M., Ali, F.I., Ahmed, S., Wadood, A., Rama, N.H., Uddin, R., Ul-Haq, Z., Khan, A., and Choudhary, M.I., ACS Med. Chem Lett., 2010, vol. 1, pp. 145–149. https://doi.org/10.1021/ml100068u

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Pervez, H., Chohan, Z.H., Ramzan, M., Nasim, F.-U.-H., and Khan, K.M., J. Enzyme Inhib. Med. Chem., 2009, vol. 24, pp. 437–446. https://doi.org/10.1080/14756360802188420

    Article  CAS  PubMed  Google Scholar 

  7. Perveen, S., Khan, K.M., Lodhi, M.A., Choudhary, M.I., Atta-ur-Rahman, and Voelter, W., Lett. Drug Des. Discov., 2008, vol. 5, pp. 401–405. https://doi.org/10.2174/157018008785777315

    Article  CAS  Google Scholar 

  8. Shamim, S., Khan, K.M., Salar, U., Ali, F., Lodhi, M.A., Taha, M., Khan, F.A., Ashraf, S., Ul-Haq, Z., Ali, M., Ali, M., and Perveen, S., Bioorg. Chem., 2018, vol. 76, pp. 37–52. https://doi.org/10.1016/j.bioorg.2017.10.021

    Article  CAS  PubMed  Google Scholar 

  9. Taha, M. and Wadood, A., Bioorg. Chem., 2018, vol. 78, pp. 411–417. https://doi.org/10.1016/j.bioorg.2018.04.007

    Article  CAS  PubMed  Google Scholar 

  10. de la Torre, A.F., Ali, A., Galetto, F.Z., Braga, A.L., Delgado, J.A.C., and Paixao, M.W., Mol. Divers., 2020, vol. 24, pp. 1–10. https://doi.org/10.1007/s11030-019-09923-w

    Article  CAS  PubMed  Google Scholar 

  11. Saeed, A., Imran, A., Channar, P.A., Shahid, M., Mahmood, W., and Iqbal, J., Chem. Biol. Drug Des., 2015, vol. 85, pp. 225–230. https://doi.org/10.1111/cbdd.12379

    Article  CAS  PubMed  Google Scholar 

  12. Aslam, M.A.S., Mahmood, S., Shahid, M., Saeed, A., and Iqbal, J., Eur. J. Med. Chem., 2011, vol. 46, pp. 5473–5479. https://doi.org/10.1016/j.ejmech.2011.09.009

    Article  CAS  PubMed  Google Scholar 

  13. Kafarski, P. and Talma, M., J. Adv. Res., 2018, vol. 13, pp. 101–112. https://doi.org/10.1016/j.jare.2018.01.007

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Pi-Sunyer, X., Postgrad Med., 2009, vol. 121, pp. 21–33. https://doi.org/10.3810/pgm.2009.11.2074

    Article  PubMed  PubMed Central  Google Scholar 

  15. Gregoire, F.M., Smas, C.M., and Sul, H.S., Physiol. Rev., 1998, vol. 78, pp. 783–809. https://doi.org/10.1152/physrev.1998.78.3.783

    Article  CAS  PubMed  Google Scholar 

  16. Zhi, J., Melia, A.T., Guerciolini, R., Chung, J., Kinberg, J., Hauptman, J.B., and Patel, I.H., Clin. Pharmacol. Ther., 1994, vol. 56, pp. 82–85. https://doi.org/10.1038/clpt.1994.104

    Article  CAS  PubMed  Google Scholar 

  17. Neovius, M., Johansson, K., and Rossner, S., Obes. Rev., 2008, vol. 9, pp. 420–427. https://doi.org/10.1111/j.1467-789X.2008.00463.x

    Article  CAS  PubMed  Google Scholar 

  18. Filippatos, T.D., Derdemezis, C.S., Gazi, I.F., Nakou, E.S., Mikhailidis, D.P., and Elisaf, M.S., DRUG Saf., 2008, vol. 31, pp. 53–65. https://doi.org/10.2165/00002018-200831010-00005

    Article  CAS  PubMed  Google Scholar 

  19. Viner, R.M., Hsia, Y., Tomsic, T., and Wong, I.C.K., Obes. Rev,. 2010, vol. 11, pp. 593–602. https://doi.org/10.1111/j.1467-789X.2009.00651.x

  20. Menteşe, E., Yılmaz, F., Emirik, M., Ülker, S., and Kahveci, B., Bioorg. Chem., 2018, vol. 76, pp. 478–486. https://doi.org/10.1016/j.bioorg.2017.12.023

    Article  CAS  PubMed  Google Scholar 

  21. Kahveci, B., Yilmaz, F., Menteşe, E., Özil, M., and Karaoǧlu, S.A. J. Heterocycl. Chem., 2014, vol. 51, pp. 982–990. https://doi.org/10.1002/jhet.1593

    Article  CAS  Google Scholar 

  22. Ali, I., Lone, M.N. and Aboul-Enein, H.Y., Med. Chem. Comm., 2017, vol. 8, pp. 1742–1773. https://doi.org/10.1039/C7MD00067G

    Article  CAS  Google Scholar 

  23. Ajani, O.O., Tolu-Bolaji, O.O., Olorunshola, S.J., Zhao, Y., and Aderohunmu, D. V. J. Adv. Res., 2017, vol. 8, p. 703. https://doi.org/10.1016/j.jare.2017.09.003

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  24. El Rashedy, A.A. and Aboul-Enein, Y.H., Mini-Rev. Med. Chem., 2013, vol. 13, pp. 399–407. https://doi.org/10.2174/1389557511313030008

    Article  CAS  PubMed  Google Scholar 

  25. Menteşe, E., Yilmaz, F., Baltaş, N., Bekircan, O., and Kahveci, B., J. Enzyme Inhib. Med. Chem., 2015, vol. 30, p. 435–441. https://doi.org/10.3109/14756366.2014.943203

    Article  CAS  PubMed  Google Scholar 

  26. Pandy, K. M., Krishman, P., and Paratharaj, S., J. Het. Chem., 2022, vol. 59, pp. 1665–1883. https://doi.org/10.1002/jhet.4519

    Article  CAS  Google Scholar 

  27. Ponticello, G.S., Freedman, M.B., Habecker, C.N., Lyle, P.A., Schwam, H., Varga, S.L., Christy, M.E., Randall, W.C., and Baldwin, J.J., J. Med. Chem., 1987, vol. 30, pp. 591–597. https://doi.org/10.1021/jm00387a002

    Article  CAS  PubMed  Google Scholar 

  28. Ivasiv, V., Albertini, C., Gonçalves, A., Rossi, M., and Bolognesi, M., Curr. Top. Med. Chem., 2019, vol. 19, p. 1694–1711. https://doi.org/10.2174/1568026619666190619115735

    Article  CAS  PubMed  Google Scholar 

  29. Menteşe, E., Yilmaz, F., Baltaş, N., Bekircan, O., and Kahveci, B., J. Enzyme Inhib. Med. Chem., 2015, vol. 30, pp. 435–441. https://doi.org/10.3109/14756366.2014.943203

    Article  CAS  PubMed  Google Scholar 

  30. Menteşe, E., Emirik, M., and Sökmen, B.B., Bioorg. Chem., 2019, vol. 86, pp. 151–158. https://doi.org/10.1016/j.bioorg.2019.01.061

    Article  CAS  PubMed  Google Scholar 

  31. Bendicho, S., Trigueros, M.C., Hernández, T., and Martín, O., J. Dairy Sci., 2001, vol. 84, pp. 1590–1596. https://doi.org/10.3168/jds.S0022-0302(01)74592-4

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ACKNOWLEDGMENTS

The authors thank all the colleagues in the project unit for this support.

Funding

This work was supported by Research Fund of Recep Tayyip Erdogan University under the Project Number of FBA-2020-1071.

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Contributions

Authors FY and EM designed the experiments, synthesized the molecules and carried out spectral studies. Author BBS carried our biological activity studies.

Corresponding author

Correspondence to Fatih Yilmaz.

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The data that support the findings of this study are available from the corresponding author upon reasonable request. This article does not contain any studies involving animals or human participants performed by any of the authors. Informed consent was not required for this article. No conflict of interest was declared by the authors.

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Yilmaz, F., Menteşe, E. & Sökmen, B.B. Synthesis of Some Benzimidazole-Thiophene Hybrids as Potential Urease and Lipase Inhibitors. Russ J Bioorg Chem 49, 1293–1300 (2023). https://doi.org/10.1134/S1068162023060092

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