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Synthesis, Characterization, and Molecular Docking Study of N-[4-(1H-Benzimidazol-2-yl)-1,3-thiazol-2-yl]-1-[(E)-phenyldiazenyl)-1-phenylmethanimines

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Abstract

A series of new benzamidine derivatives have been synthesized in good yields by involving 1-(1H-benzimidazol-2-yl)-2-bromoethanone, 4-(1H-benzimidazol-2-yl)-1,3-thiazol-2-amine, and N-benzyli­dene-4-(1H-benzimidazol-2-yl)-1,3-thiazol-2-amine as reactive intermediates. The synthesized compounds were characterized by spectral data. Molecular docking study of N-(4-(1H-benzimidazol-2-yl)-1,3-thiazol-2-yl]-1-[(E)-phenyldiazenyl]-1-phenylmethanimine has been carried out as a representative case.

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REFERENCES

  1. Pardeshi, V.A.S., Chundawat, N.S., Pathan, S.I., Sukhwal, P., Chundawat, T.P.S., and Singh, G.P., Synth Commun., 2021, vol. 51, no. 4, p. 485. https://doi.org/10.1080/00397911.2020.1841239

    Article  CAS  Google Scholar 

  2. Sharma, S. and Rauf, A., Chin. Chem. Lett., 2009, vol. 20, no. 10, p. 1145. https://doi.org/10.1016/j.cclet.2009.04.032

    Article  CAS  Google Scholar 

  3. Beltran-Hortelano, I., Alcolea, V., Font, M., and Perez-Silanes, S., Eur. J. Med. Chem., 2020, vol. 206, article ID 112692. https://doi.org/10.1016/j.ejmech.2020.112692

  4. Joshi, B., Panda, S.K., Jouneghani, R.S., Liu, M., Parajuli, N., Leyssen, P., Neyts, J., and Luyten, W., Evidence-Based Complementary Altern. Med., 2020, article ID 1043471. https://doi.org/10.1155/2020/1043471

  5. Smaili, A., Jebbari, S., Rifai, L.A., Faize, L., Koussa, T., Sir, H.A., Makroum, K., Belfaiza, M., El Kihel, A., Ahbala, M., Venisse, J.S., and Faize, M., Phytoparasitica, 2019, vol. 47, no. 5, p. 733. https://doi.org/10.1007/s12600-019-00764-9

    Article  CAS  Google Scholar 

  6. Patel, V.M., Patel, N.B., Chan-Bacab, M.J., and Rivera, G., Synth. Commun., 2020, vol. 50, no. 6, p. 858. https://doi.org/10.1080/00397911.2020.1725057

    Article  CAS  Google Scholar 

  7. Gut, J., Ang, K.K., Legac, J., Arkin, M.R., Rosen­thal, P.J., and McKerrow, J.H., J. Microbiol. Methods, 2011, vol. 84, no. 3, p. 398. https://doi.org/10.1016/j.mimet.2010.12.026

    Article  CAS  PubMed  Google Scholar 

  8. North, T.W., Sequar, G., Townsend, L.B., Drach, J.C., and Barry, P.A., Antimicrob. Agents Chemother., 2004, vol. 48, no. 7, p. 290. https://doi.org/10.1128/AAC.48.7.2760-2765.2004

    Article  CAS  Google Scholar 

  9. Desai, N.C., Shihory, N.R., Kotadiya, G.M., and Desai, P., Eur. J. Med. Chem., 2014, vol. 82, p. 480. https://doi.org/10.1016/j.ejmech.2014.06.004

    Article  CAS  PubMed  Google Scholar 

  10. Cheong, J.E., Zaffagni, M., Chung, I., Xu, Y., Wang, Y., Jernigan, F.E., Zetter, B.R., and Sun, L., Eur. J. Med. Chem., 2018, vol. 144, p. 372. https://doi.org/10.1016/j.ejmech.2017.11.037

    Article  CAS  PubMed  Google Scholar 

  11. Narasimhan, B., Sharma, D., and Kumar, P., Med. Chem. Res., 2012, vol. 21, no. 3, p. 269. https://doi.org/10.1007/s00044-010-9533-9

    Article  CAS  Google Scholar 

  12. Nile, S.H., Kumar, B., and Park, S.W., Chem. Biol. Drug Des., 2013, vol. 82, no. 3, p. 290. https://doi.org/10.1111/cbdd.12141

    Article  CAS  PubMed  Google Scholar 

  13. Wang, X.J., Xi, M.Y., Fu, J.H., Zhang, F.R., Cheng, G.F., Yin, D.L., and You, Q.D., Chin. Chem. Lett., 2012, vol. 23, no. 6, p. 707. https://doi.org/10.1016/j.cclet.2012.04.020

    Article  CAS  Google Scholar 

  14. Tahlan, S., Kumar, S., Kakkar, S., and Narasimhan, B., BMC Chem., 2019, vol. 13, article no. 66. https://doi.org/10.1186/s13065-019-0579-6

  15. Rouf, A. and Tanyeli, C., Eur. J. Med. Chem., 2015, vol. 97, p. 911. https://doi.org/10.1016/j.ejmech.2014.10.058

    Article  CAS  PubMed  Google Scholar 

  16. El-Enany, W.A.M.A., Gomha, S.M., El-Ziaty, A.K., Hussein, W., Abdulla, M.M., Hassan, S.A., Sallam, H.A., and Ali, R.S., Synth. Commun., 2020, vol. 50, no. 1, p. 85. https://doi.org/10.1080/00397911.2019.1683207

    Article  CAS  Google Scholar 

  17. Maghraby, M.T., Abou-Ghadir, O.M.F., AbdelMoty, S.G., Ali, A.Y., and Salem, O.I.A., Bioorg. Med. Chem., 2020, vol. 28, no. 7, article ID 115403. https://doi.org/10.1016/j.bmc.2020.115403

  18. Mishra, C.B., Kumari, S., and Tiwari, M., Eur. J. Med. Chem., 2015, vol. 92, p. 1. https://doi.org/10.1016/j.ejmech.2014.12.031

    Article  CAS  PubMed  Google Scholar 

  19. Qin, Y.J., Wang, P.F., Makawana, J.A., Wang, Z.C., Wang, Z.N., Yan, G., Jiang, A.Q., and Zhu, H.L., Bioorg. Med. Chem. Lett., 2014, vol. 22, p. 5279. https://doi.org/10.1016/j.bmcl.2014.09.054

    Article  CAS  Google Scholar 

  20. Madni, M., Hameed, S., Ahmed, M.N., Tahir, M.N., Al-Masoudi, N.A., and Pannecouque, C., Med. Chem. Res., 2017, vol. 26, no. 10, p. 2653. https://doi.org/10.1007/s00044-017-1963-1

    Article  CAS  Google Scholar 

  21. Gupta, V. and Kant, V., Science International, 2013, vol. 1, no. 7, p. 253. https://doi.org/10.17311/sciintl.2013.253.260

  22. Hosny, M.A., Zaki, Y.H., Mokbel, W.A., and Abdelhamid, A.O., BMC Chem., 2019, vol. 13, article no. 37. https://doi.org/10.1186/s13065-019-0559-x

  23. Bondock, S., Khalifa, W., and Fadda, A.A., Eur. J. Med. Chem., 2007, vol. 42, no. 7, p. 948. https://doi.org/10.1016/j.ejmech.2006.12.025

    Article  CAS  PubMed  Google Scholar 

  24. Gjorgjieva, M., Tomasic, T., Barancokova, M., Katsamakas, S., Ilas, J., Tammela, P., Peterlin Masic, L., and Kikelj, D., J. Med. Chem., 2016, vol. 59, no. 19, p. 8941. https://doi.org/10.1021/acs.jmedchem.6b00864

    Article  CAS  PubMed  Google Scholar 

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ACKNOWLEDGMENTS

The authors thank Jawaharlal Nehru Technological University, Hyderabad, India, for providing necessary facilities to carry out this work.

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Correspondence to Ch. Venkata Ramana Reddy.

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Reddy, S.R., Reddy, G.G., Reddy, C.V.R. et al. Synthesis, Characterization, and Molecular Docking Study of N-[4-(1H-Benzimidazol-2-yl)-1,3-thiazol-2-yl]-1-[(E)-phenyldiazenyl)-1-phenylmethanimines. Russ J Org Chem 58, 858–864 (2022). https://doi.org/10.1134/S107042802206015X

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