Research Article
BibTex RIS Cite
Year 2021, Volume: 42 Issue: 3, 649 - 655, 24.09.2021
https://doi.org/10.17776/csj.867783

Abstract

References

  • [1] Akyüz G., Mentese E., Emirik M., Baltaş N., Synthesis and molecular docking study of some novel 2,3-disubstituted quinazolin-4(3H)-one derivatives as potent inhibitors of urease, Bioorganic Chemistry, 80 (2018) 121-128.
  • [2] Amtul A.Z., Rahman A., Siddiqui R.A., Choudhary M.I., Chemistry and mechanism of urease inhibition, Curr. Med. Chem., 9 (2002) 1323–1348.
  • [3] Upadhyay L.S.B., Urease Inhibitors: A review, Indian Journal of Biotechnology, 11 (2012) 381-388.
  • [4] Mumtaz A., Arshad J., Saeed A., Nawaz M., Iqbal J., Synthesis, characterization and urease inhibition studies of transition metal complexes of thioureas bearing ibuprofen moiety, J. Chil. Chem. Soc., 63(2) (2018) 3934-3940.
  • [5] Akyüz G., Mentese E., Emirik M, Baltaş N., Synthesis and molecular docking study of some novel 2,3-disubstituted quinazolin-4(3H)-one derivatives as potent inhibitors of urease, Bioorganic Chemistry, 80 (2018) 121-128.
  • [6] Mentese E., Akyüz G., Yılmaz F., Baltaş N., Emirik M., Synthesis of some novel quinazolin‐4(3H)‐one hybrid molecules as potent urease inhibitors, Arch pharm., 351(12) (2018)180-182.
  • [7] Mentese E., Yılmaz F., Emirik M., Ülker S., Kahveci B. Synthesis, molecular docking and biological evaluation of some benzimidazole derivatives as potent pancreatic lipase inhibitors, Bioorganic Chemistry, 76 (2018) 478-486.
  • [8] Usta A., Yılmaz F., Kapucu G., Baltaş N., Mentese E., Synthesis of some new benzimidazole derivatives with their antioxidant activities, Letters in Organic Chemistry, 12 (4) (2015) 227-232.
  • [9] Palit R., Kumar R., Saraswat N., Wal A., Upadhyaya K., Benzimidazole: an overview, Int. J. Res. Ayurveda Pharm., 7(6) (2016) 68-73.
  • [10] Mentese E., Yılmaz F., Mutlu F., Kahveci B., Synthesis of new coumarin containing benzimidazole derivatives, Journal of Chemical Research, (39) (2015) 645-648.
  • [11] Mentese E., Yılmaz F., Emirik M., Ulker S., Kahveci B., Synthesis, molecular docking and biological evaluation of some benzimidazole derivatives as potent pancreatic lipase inhibitors, Bioorganic Chemistry,76 (2018) 478-486.
  • [12] Baltas N., Yılmaz F., Mentese E., Synthesis, antioxidant, xanthine oxidase and urease inhibitory activities of some chlorine containing benzimidazoles, J. Biol. Chem., 44 (3) (2016) 293-305.
  • [13] Kajal A., Bala S., Kamboj S., Schif bases: a versatile pharmacophore, J. Catal., (2013) 1–14.
  • [14] Fonkui T.Y., Ikhile M.I., Njobech P.B., Ndintech D.T., Benzimidazole Schif base derivatives: synthesis, characterization and antimicrobial activity, BMC Chemistry, 13 (2019) 127.
  • [15] Mentese E., Yılmaz F., Baltaş N., Bekircan O., Kahveci B., Synthesis and antioxidant activities of some new triheterocyclic compounds containing benzimidazole, thiophene, and 1,2,4-triazole rings, J. Enzyme Inhib. Med. Chem., 30(3) (2015) 435-41.
  • [16] Pinner A., Die Imidoa¨ther und ihre Derivate, 1 Auflage, Oppenheim: Berlin, (1892).
  • [17] M.W. Weatherburn. Phenol-hypochlorite reaction for determination of ammonia, Anal. Chem., 39 (1967) 971- 974.

Synthesis of Benzimidazole derivatives containing Schiff base exhibiting antiurease activities

Year 2021, Volume: 42 Issue: 3, 649 - 655, 24.09.2021
https://doi.org/10.17776/csj.867783

Abstract

In this study some novel Schiff bases derivatives of benzimidazole containing thiophene ring were designed and synthesized by using various aldehydes. Seven different aromatic aldehydes with various side groups were used for synthesized. 1H-NMR, 13C-NMR spectra and LC-MS were used to identify all of the compounds. All synthesized compounds anti urease activities were calculated according to phenol-hypochlorite method by Weatherburn. The results indicated that all compounds have anti urease activity between 12.70±0.11 µg/mL and 14.00±0.08 µg/mL IC50 values. Especially the compound N'-[(1E)-2-furylmethylene]-2-[5,6-dimethyl-2-(2-thienylmethyl)-1H-benzimidazol-1-yl]acetohydrazide (5g) has very close IC50 value (12.70±0.11 µg/mL) to thiourea (12.60±0.10 µg/mL) that is the standard inhibitor. 5g bearing furan ring at the N-3 position on the benzimidazole nucleus has the smallest volume of side group than others.

References

  • [1] Akyüz G., Mentese E., Emirik M., Baltaş N., Synthesis and molecular docking study of some novel 2,3-disubstituted quinazolin-4(3H)-one derivatives as potent inhibitors of urease, Bioorganic Chemistry, 80 (2018) 121-128.
  • [2] Amtul A.Z., Rahman A., Siddiqui R.A., Choudhary M.I., Chemistry and mechanism of urease inhibition, Curr. Med. Chem., 9 (2002) 1323–1348.
  • [3] Upadhyay L.S.B., Urease Inhibitors: A review, Indian Journal of Biotechnology, 11 (2012) 381-388.
  • [4] Mumtaz A., Arshad J., Saeed A., Nawaz M., Iqbal J., Synthesis, characterization and urease inhibition studies of transition metal complexes of thioureas bearing ibuprofen moiety, J. Chil. Chem. Soc., 63(2) (2018) 3934-3940.
  • [5] Akyüz G., Mentese E., Emirik M, Baltaş N., Synthesis and molecular docking study of some novel 2,3-disubstituted quinazolin-4(3H)-one derivatives as potent inhibitors of urease, Bioorganic Chemistry, 80 (2018) 121-128.
  • [6] Mentese E., Akyüz G., Yılmaz F., Baltaş N., Emirik M., Synthesis of some novel quinazolin‐4(3H)‐one hybrid molecules as potent urease inhibitors, Arch pharm., 351(12) (2018)180-182.
  • [7] Mentese E., Yılmaz F., Emirik M., Ülker S., Kahveci B. Synthesis, molecular docking and biological evaluation of some benzimidazole derivatives as potent pancreatic lipase inhibitors, Bioorganic Chemistry, 76 (2018) 478-486.
  • [8] Usta A., Yılmaz F., Kapucu G., Baltaş N., Mentese E., Synthesis of some new benzimidazole derivatives with their antioxidant activities, Letters in Organic Chemistry, 12 (4) (2015) 227-232.
  • [9] Palit R., Kumar R., Saraswat N., Wal A., Upadhyaya K., Benzimidazole: an overview, Int. J. Res. Ayurveda Pharm., 7(6) (2016) 68-73.
  • [10] Mentese E., Yılmaz F., Mutlu F., Kahveci B., Synthesis of new coumarin containing benzimidazole derivatives, Journal of Chemical Research, (39) (2015) 645-648.
  • [11] Mentese E., Yılmaz F., Emirik M., Ulker S., Kahveci B., Synthesis, molecular docking and biological evaluation of some benzimidazole derivatives as potent pancreatic lipase inhibitors, Bioorganic Chemistry,76 (2018) 478-486.
  • [12] Baltas N., Yılmaz F., Mentese E., Synthesis, antioxidant, xanthine oxidase and urease inhibitory activities of some chlorine containing benzimidazoles, J. Biol. Chem., 44 (3) (2016) 293-305.
  • [13] Kajal A., Bala S., Kamboj S., Schif bases: a versatile pharmacophore, J. Catal., (2013) 1–14.
  • [14] Fonkui T.Y., Ikhile M.I., Njobech P.B., Ndintech D.T., Benzimidazole Schif base derivatives: synthesis, characterization and antimicrobial activity, BMC Chemistry, 13 (2019) 127.
  • [15] Mentese E., Yılmaz F., Baltaş N., Bekircan O., Kahveci B., Synthesis and antioxidant activities of some new triheterocyclic compounds containing benzimidazole, thiophene, and 1,2,4-triazole rings, J. Enzyme Inhib. Med. Chem., 30(3) (2015) 435-41.
  • [16] Pinner A., Die Imidoa¨ther und ihre Derivate, 1 Auflage, Oppenheim: Berlin, (1892).
  • [17] M.W. Weatherburn. Phenol-hypochlorite reaction for determination of ammonia, Anal. Chem., 39 (1967) 971- 974.
There are 17 citations in total.

Details

Primary Language English
Journal Section Natural Sciences
Authors

Gülay Akyüz 0000-0002-4452-7387

Publication Date September 24, 2021
Submission Date January 25, 2021
Acceptance Date September 20, 2021
Published in Issue Year 2021Volume: 42 Issue: 3

Cite

APA Akyüz, G. (2021). Synthesis of Benzimidazole derivatives containing Schiff base exhibiting antiurease activities. Cumhuriyet Science Journal, 42(3), 649-655. https://doi.org/10.17776/csj.867783