Russian Journal of General Chemistry

, Volume 87, Issue 12, pp 3017–3022 | Cite as

Synthesis and Antimicrobial Activity of Novel Substituted 4-[3-(1H-Benzimidazol-2-yl)-4-hydroxybenzyl]-2-(1H-benzimidazol-2-yl)phenol Derivatives

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Abstract

A series of novel substituted bis-benzimidazole derivatives were synthesized by reaction of 5,5′-methylenebis(2-hydroxybenzaldehyde) with various substituted o-phenylenediamines in glacial acetic acid. The structure of the newly synthesized compounds was elucidated by 1H and 13C NMR, FT-IR, and MS spectra, and their antimicrobial activity against gram positive and gram negative bacteria and antifungal activity were evaluated. The thienyl-substituted derivative showed significant activity against Bacillus licheniformis, Bacillus subtilis, Staphylococcus aureus, Klebsiella pneumonia (bacteria), and Fusarium solani (fungi). The activities of the fluoro-substituted substituted derivative against some bacterial strains and of the thienyl-substituted derivative against fungi were found to be similar to those of standard drugs.

Keywords

bis-benzimidazoles acetic acid antibacterial activity antifungal activity 

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References

  1. 1.
    Shadia, A.G., Ahmed, S.A., Mireya, L.R., Sean, M., and HodaI, E.D., Eur. J. Chem., 2010, vol. 1, p. 67. doi 10.5155/eurjchem.1.2.67-72.1CrossRefGoogle Scholar
  2. 2.
    Hayakawa, I., Shioya, R., Agatsuma, T., Furukawa, H., Naruto, S., and Sugano, Y., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 455. doi 10.1016/j.bmcl.2003.10.039CrossRefGoogle Scholar
  3. 3.
    Galal, S.A., Abd, E.A., Abdullah, M.M., and Diwani, H.I., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 2420. doi 10.1016/j.bmcl.2009.03.069CrossRefGoogle Scholar
  4. 4.
    Jabali, J.V., Keyur, P.T, and Rahul, S.K., Adv. Appl. Sci. Res., 2011, vol. 2, no. 3, p. 89.Google Scholar
  5. 5.
    Can-Eke, B., Puskullu, M.O., Buyukbingol, E., and Iscan, M., Chem.-Biol. Interact., 1998, vol. 113, p. 65. doi 10.1016/S0009-2797(98)00020-9CrossRefGoogle Scholar
  6. 6.
    Kus, C., Ayhan-Kilcigil, G., Can-Eke, B., and iŞcan, M., Arch. Pharm. Res., 2004, vol. 27, p. 156. doi 10.1007/BF02980099CrossRefGoogle Scholar
  7. 7.
    Ayhan-Kilcigil, G., Kus, C., Çoban, T., Can-Eke, B., and Iscan, M., J. Enzyme Inhib. Med. Chem., 2004, vol. 19, p. 129. doi 10.1080/1475636042000202017CrossRefGoogle Scholar
  8. 8.
    Göker, H., Ayhan-Kilcigil, G., Tunçbilek, M., Kus, C., Ertan, R., Kendi, E., Özbey, S., Fort, M., Garcia, C., and Farré, A.J., Heterocycles, 1999, vol. 51, p. 2561. doi 10.3987/COM-99-8585CrossRefGoogle Scholar
  9. 9.
    Abdel Rahman, A.E., Mahmoud, A.M., El Naggar, G.M., and El Sherief, H.A., Pharmazie, 1983, vol. 38, p. 589.Google Scholar
  10. 10.
    Soliman, F.S.G., Rida, S.M., Badawey, E.A.M., and Kappe, T., Arch. Pharm., 1984, vol. 317, p. 951. doi 10.1002/ardp.19843171110CrossRefGoogle Scholar
  11. 11.
    Coburn, R.A., Clark, M.T., Evans, R.T., and Genco, R.J., J. Med. Chem., 1987, vol. 30, p. 205.CrossRefGoogle Scholar
  12. 12.
    Habib, N.S., Abdel Hamid, S., and El Hawash, M., Farmaco, 1989, vol. 44, p. 1225.Google Scholar
  13. 13.
    Göker, H., Kuş, C., Boykin, D.W., Yildiz, S., and Altanlar, N., Bioorg. Med. Chem., 2002, vol. 10, p. 2589. doi 10.1016/S0968-0896(02)00103-7CrossRefGoogle Scholar
  14. 14.
    Penning, T.D., Zhu, G.-D., Gandhi, V.B., Gong, J., Thomas, S., Lubisch, W., Grandel, R., Wernet, W., Park, Ch.H., Fry, E.H., Liu, X.-S., Shi, Y., Klinghofer, V., Johnson, E.F., Donawho, Ch.K., Frost, D.J., Bontcheva-Diaz, V., Bouska, J.J., Olson, A.M., Marsh, K.C., Luo, Y., Rosenberg, S.H., and Giranda, V.L., Bioorg. Med. Chem., 2008, vol. 16, p. 6965. doi 10.1016/j.Bmc.2008. 05.044CrossRefGoogle Scholar
  15. 15.
    Devender, M., Anil, V., Jalapathi, P., Srinivasrao, V., Parthasarathy, T., and Rajakomuraiah, T., Med. Chem. Res., 2013, vol. 22, p. 5481. doi 10.1007/s00044-013-0543-2CrossRefGoogle Scholar
  16. 16.
    Jalapathi, P., Devender, M., Umapathi Reddy, N., and Rajakomuraiah, T., Lett. Drug Des. Discovery, 2012, vol. 9, p. 471. doi 10.2174/157018012800389304CrossRefGoogle Scholar
  17. 17.
    Marvel, C. and Sand Turkey, N., J. Am. Chem. Soc., 1957, vol. 79, p. 6000.CrossRefGoogle Scholar
  18. 18.
    Shankar, B., Jalapathi, P., Sunitha, V., and Karunakar Rao, K., Pharma Chem., 2016, vol. 8, p. 192.Google Scholar
  19. 19.
    Davood, A., Mojgan, P., Behrooz, M., Mehrangiz, S., and Razieh Nejat, Y., J. Serb. Chem. Soc., 2010, vol. 75, p. 1181.CrossRefGoogle Scholar
  20. 20.
    Keche, A.P., Hatnapure, G.D., Tale, R.T., Rodge, A.H., Birajdar, S.S., and Kamble, V.M., Med. Chem. Res., 2013, vol. 22, p. 1480. doi 10.1007/s00044-012-0144-5CrossRefGoogle Scholar
  21. 21.
    Shankar, B., Jalapathi, P., Ramesh, M., Kishore Kumar, A., Ragavender, M., and Bharath G., Russ. J. Gen. Chem., 2016, vol. 86, p. 1711. doi 10.1134/S10703632160 7029XCrossRefGoogle Scholar
  22. 22.
    Shankar, B., Jalapathi, P., Nagamani, M., Bharath, G., and Karunakar Rao, K., Monatsh Chem., 2017, vol. 148, p. 999. doi 10.1007/s00706-016-1838-zCrossRefGoogle Scholar
  23. 23.
    Bhavanarushi, S., Kanakaiah, V., Gandu, B., Gangagnirao, A., and Vatsala, R., Med. Chem. Res., 2014, vol. 23, no. 1, p. 158. doi 10.1007/s00044-013-0623-3CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2017

Authors and Affiliations

  1. 1.Department of Chemistry, University College of ScienceOsmania UniversitySaifabad, HyderabadIndia
  2. 2.Bioengineering and Environmental Sciences DivisionIndian Institute of Chemical TechnologyHyderabadIndia

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