Synthesis and Antioxidant Properties of New Benzimidazole Derivatives

Bu çalışmada yeni benzimidazol türevleri sentezlenmiştir. İnce Tabaka Kromatografisi (TLC) ve erime noktaları ile saflık kontrolleri yapıldıktan sonra yapıları kütle spektroskopisi, 1H, 13C NMR ve element analizi teknikleri ile kanıtlanmıştır. Elde edilen bileşiklerin antioksidan aktiviteleri, 2, 2-difenil-1-pikrilhidrazil (DPPH) radikal temizleme aktivitesi, lipit peroksidasyon inhibisyonu ve etoksresorufin O-deetilaz (EROD) enzim aktivitesi üzerindeki etkileri açısından araştırılmıştır. Bileşikler, standart bileşik ile karşılaştırıldığında DPPH radikal temizleme aktivitesi ve lipit peroksidasyon inhibisyonu açısından genellikle orta derecede ve EROD enzim aktivitesi üzerinde iyi bir etkiye sahip olduğu gözlenmiştir.

Synthesis and Antioxidant Properties of New Benzimidazole Derivatives

In this study, new benzimidazole derivatives were synthesized. After purity checks were made with Thin Layer Chromatography (TLC) and melting points, their structures were proved by mass spectroscopy, 1H, 13C NMR and elemental analysis technique. Antioxidant activities of the obtained materials were searched in terms of their effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, lipid peroxidation inhibition and ethoxyresorufin O-deethylase (EROD) enzyme activity. It was observed the compounds were generally moderately active in terms of DPPH radical scavenging activity and lipid peroxidation inhibition compared to the standard compound and had a good effect on EROD enzyme activity.

___

1. Patlevic P., Vaskov J., Svorc B., Vasko L., Svorc P., ''Reactive oxygen species and antioxidant defense in human gastrointestinal diseases'', Integrative Medicine Research, 5: 250-258, (2016). doi: 10.1016/j.imr.2016.07.004

2. Desai K. G., Desai K. R., ''Green Route for The Heterocyclization of 2-Mercaptobenzimidazole Into Β-Lactum Segment Derivatives Containing–CONH– Bridge with Benzimidazole: Screening In Vitro Antimicrobial Activity With Various Microorganisms'', Bioorganic & Medicinal Chemistry,14: 8271-8279, (2006). doi: 10.1016/j.bmc.2006.09.017

3. Vazquez G. N., Vilehis M. R., Mulia L. Y., Melendez V., Gerena L., et al., ''Synthesis and Antiprotozoal Activity of Some 2-(Trifluoromethyl)-1HBenzimidazole Bioisosteres'', European Journal of Medicinal Chemistry, 41:135-141, (2006). doi: 10.1016/j.ejmech.2005.09.00

4. Mavrova A. T., Anichina K. K., Vuchev D. I., ''Antihelminthic Activity of Some Newly Synthesized5(6)-(un)substituted-1H-Benzimidazol-2-yl-thioacetylpiperazine Derivatives'', European Journal of Medicinal Chemistry, 41:1412-1420, (2006). doi: 10.1016/j.ejmech.2006.07.005

5. Kılcıgil G. A., Altanlar N., ''Synthesis and Antifungal Properties of Some Benzimidazole Derivatives'', Turkish Journal of Chemistry, 30: 223-228, (2006).

6. Hwu J. R., Singha R., Hong S. C., Chang Y. H., Das A. R., et al., ''Synthesis of New Benzimidazole-Coumarin Conjugates as Anti-Hepatitis C Virus Agents'', Antiviral Research, 77: 157-162, (2008). doi: 10.1016/j.antiviral.2007.09.003

7. Tremblay M., Bonneau P., Bousquet Y., Deroy P., Duan J et al., ''Inhibition of HIV-1 Capsid Assembly: Optimization of the Antiviral Potency by Site Selective Modifications at N1, C2 and C16 of a 5-(5-Furan-2-yl-Pyrazol-1-yl)-1H-Benzimidazole Scaffold'', Bioorganic & Medicinal Chemistry Letters, 22: 7512-7517, (2012). doi: 10.1016/j.bmcl.2012.10.034

8. Uchida M., Chihiro M., Morita S., Yamashita H., Yamasaki K et al., ''Synthesis and Antiulcer Activity of 4-Substituted 8-[ (2-Benzimidazolyl) Sulfinylmethyl ]-1,2,3,4 -Tetrahydro quinolines and Related Compounds'', Chemical and Pharmaceutical Bulletin, 38: 1575-1586, (1990). doi: 10.1248/cpb.38.1575

9. Grassi A., Ippen J., Bruno M., Thomas G. A., ''Thiazolylamino Benzimidazole Derivative with Gastroprotective Properties in the Rat'', European Journal of Pharmacology, 195: 251-259, (1991). doi: 10.1016/0014-2999(91)90543-Y

10. Achar K. C., Hosamani K. M., Seetharamareddy H. R., ''In-Vivo Analgesic and Anti-Inflammatory Activities of Newly Synthesized Benzimidazole Derivatives'' European Journal of Medicinal Chemistry, 45: 2048-2054, (2010). doi: 0.1016/j.ejmech.2010.01.029

11.Thakurdesai P. A., Wadodkar S. G., Chopade C. T., ''Synthesis and Anti Inflammatory Activity of Some Benzimidazole-2-Carboxylic Acids'', Pharmacologyonline, 1: 314–329, (2007).

12. Iemura R., Kawashima T., Fukuda T., Ito K., Tsukamoto G., ''Synthesis of 2-(4-Substituted-1-Piperazinyl) Benzimidazoles as H1-Antihistaminic Agents'', Journal of Medicinal Chemistry, 29: 1178-1183, (1986). doi: 0022-2623/86/1829-1183$01.50/0

13. Nakano H., Inoue T., Kawasaki N., Miyataka H., Matsumoto H., et al., ''Synthesis of Benzimidazole Derivatives as Antiallergic Agents with 5-Lipoxygenase Inhibiting Action'', Chemical and Pharmaceutical Bulletin, 47:1573-1578, (1999). doi: 10.1248/cpb.47.1573

14. Naka T., ''Angiotensin II Receptor Antagonist Activities and Mode of Action of Benzimidazole-7-Carboxylic Acid Derivatives'', Nihon Rinsho, 51: 1575-1579, (1993).

15. Shingalapur R. V., Hosamani K. M., Keri R. S., ''Synthesis and Evaluation of In Vitro Anti-Microbial and Anti-Tubercular Activity of 2-Styryl Benzimidazoles'', European Journal of Medicinal Chemistry, 44: 4244-4248, (2009). doi: 10.1016/j.ejmech.2009.05.021

16. Siddiqui N., Alam M. S., Sahu M., Yar M. S., Alam O., et al., ''Antidepressant, Analgesic Activity and SAR Studies of Substituted Benzimidazoles'', Asian Journal of Pharmaceutical Research, 6: 170-174, (2016). doi: 10.5958/2231-5691.2016.00024.1

17. Hemalatha S., Ayyappan T., Shanmugam S., Nagavalli S., Kurubha T. S., ''Evaluation of antidiabetic and diuretic activity of polyherbal formulation'', Indian Journal of Traditional Knowledge, 5: 468-470, (2006).

18. Kumar J. R., Jat J. L., Pathak D. P., ''Synthesis of Benzimidazole Derivatives: as Anti-Hypertensive Agents'', E-Journal of Chemistry, 3: 278-285, (2006). doi: 10.1155/2006/765712

19. Kerimov I., Kilcigil A, G., Eke B. C., Altanlar N., Iscan M., ''Synthesis, Antifungal and Antioxidant Screening of Some Novel Benzimidazole Derivatives'', Journal of Enzyme Inhibition and Medicinal Chemistry, 22: 696-701, (2007). doi: 10.1080/14756360701228558

20. Kilcigil A. G., Kuş C., Özdamar E. D., Can B., İscan M., ''Synthesis and Antioxidant Capacities of Some New Benzimidazole Derivatives'', Archiv der Pharmazie, 340: 607–611, (2007). doi: 10.1002/ardp.200700088

21. Ateş-Alagöz Z., Kuş C., Çoban T., ''Synthesis and Antioxidant Properties of Novel Benzimidazoles Containing Substituted Indole or 1,1,4,4-Tetramethyl-1,2,3,4-Tetrahydro-Naphthalene Fragments'', Journal of Enzyme Inhibition and Medicinal Chemistry, 20: 325–331, (2005). doi: 10.1080/14756360500131706

22. Sharma R., Bali A., Chaudhari, B. B., ''Synthesis of Methanesulphonamid -Benzimidazole Derivatives as Gastro-Sparing Antiinflammatory Agents with Antioxidant Effect'', Bioorganic & Medicinal Chemistry Letters, 27: 3007–3013, (2017). doi: 10.1016/j.bmcl.2017.05.017

23. Castro A. R., Rivera I. L., Rojas L. C. A., Vazquez G., Rodríguez A. N., ''Synthesis and Preliminary Evaluation of Selected 2-Aryl-5(6)-Nitro-1H-Benzimidazole Derivatives as Potential Anticancer Agents'', Archives of Pharmacal Research, 34: 181-189, (2011). doi: 10.1007/s12272-011-0201-5

24. Demirayak S., Kayagil I., Yurttas L., ''Microwave Supported Synthesis of Some Novel 1,3-Diarylpyrazino-[1,2-A]-Benzimidazole Derivatives and Investigation of Their Anticancer Activities'', European Journal of Medicinal Chemistry, 46: 411-416, (2011). doi: 10.1016/j.ejmech.2010.11.007

25. Nail M. S., Rosario S., Frederic G., Jean-Claude G. B., ''Benzothiazole-and Benzoxazole-Substituted Pyridine-2-Carboxylates as Efficient Sensitizers of Europium Luminescence'', Inorganic Chemistry, 48: 6178–6191, (2009). doi: 10.1021/ic9005136

26. Ma X., Qui X., Jin R., Kang C., Gao L., ''Synthesis and Properties of Fluorescence Poly (Benzoxazole–Imide) s Containing Naphthalene'', High Performance Polymers, 27: 734–741, (2015). doi: 10.1177/0954008314559552

27. Myung G. C., Sang H. L., Yun U. J., Ja M. H., Suk K. C., ''Fluorescence Signaling of BF3 Species byTransformation of an ESIPT Dye to its Difluoroboron Adduct'', Sensors and Actuators B: Chemical, 251: 713–719, (2017). doi: 0.1016/j.snb.2017.05.098

28. Salahuddin M., Mazumder A., Abdullah M. M., ''Synthesis, Characterization and Antimicrobial Activity of 1,3,4-Oxadiazole Bearing 1H-Benzimidazole Derivatives'', Arabian Journal of Chemistry, 10: 503–508, (2017). doi: 10.1016/j.arabjc.2012.10.010

29. Karaali N., ''Synthesis of Some New Benzimidazole Derivatives Containing Chlorine and Investigation of Their Antioxidant and Anti-Urease Activities'', Journal of the Turkish Chemical Society Section A: Chemistry, 5: 971-980, (2018). doi: 10.18596/jotcsa.440202

30. Mochona B., Mazzio E., Gangapurum M., Mateeva N., Redda K. K., ''Synthesis of Some Benzimidazole Derivatives Bearing 1,3,4-Oxadiazole Moiety as Anticancer Agents'', Chemical Science Transactions, 4: 534–540, (2015). doi: 10.7598/cst2015.1029

31. Kapoor A., Dhiman N., ''Anticancer Evaluation of 2-Aryl Substituted Benzimidazole Derivatives Bearing 1,3,4-Oxadiazole Nucleus'', Der Pharmacia Lettre, 8: 149-156, (2016).

32. Youssif G. M., Mohamed Y. A., Salim M. T., Inagakı F., Mukai C., et al., ''Synthesis of Some Benzimidazole Derivatives Endowed with 1,2,3-Triazole as Potential Inhibitors of Hepatitis C Virus'', Acta Pharmaceutica, 66: 219-231, (2016). doi: 10.1515/acph-2016-0014

33. Shingalapur R. V., Hosamani K. M., Keri R. S., Hugar M. H., ''Derivatives of Benzimidazole Pharmacophore: Synthesis, Anticonvulsant, Antidiabetic and DNA Cleavage Studies'', European Journal of Medicinal Chemistry, 45: 1753–1759, (2010). doi: 10.1016/j.ejmech.2010.01.007

34. Zawawi N. K., Taha M., Ahmat N., Wadood A., Ismail N. H., et al., ''Novel 2,5-Disubtituted-1,3,4-Oxadiazoles with Benzimidazole Backbone: A New Class of B-Glucuronidase Inhibitors and in Silico Studies'', Bioorganic & Medicinal Chemistry, 23: 3119-3125, (2015). doi: 10.1016/j.bmc.2015.04.081

35. Tantray M. A., Khan I., Hamid H., Alam M. S., Dhulap A., et al., ''Synthesis of Benzimidazole-Linked-1,3,4-Oxadiazole Carboxamides as GSK-3b İnhibitors with In Vivo Antidepressant Activity'', Bioorganic Chemistry, 77:393–401, (2018). doi: 10.1016/j.bioorg.2018.01.040

36. Keri R. S., Hiremathad A., Budagumpi S., Nagaraja B. M., ''Comprehensive Review in Current Developments of Benzimidazole-Based Medicinal Chemistry'', Chemical Biology & Drug Design, 86: 19–65, (2015). doi: 10.1111/cbdd.12462

37. Kerimov I., Kilcigil G. A., Can-Eke B., Altanlar N., İşcan M., ''Synthesis, Antifungal and Antioxidant Screening of Some Novel Benzimidazole Derivatives'', Journal of Enzyme Inhibition and Medicinal Chemistry, 22: 696–701, (2007). doi: 10.1080/14756360701228558

38. Kuş C., Kılcıgil G. A., Özbey S., Betu F., Kaynak I., et al., ''Synthesis and antioxidant properties of novel N-methyl-1,3,4-thiadiazol-2-amine and 4-methyl-2H-1,2,4-triazole-3(4H)-thione derivatives of benzimidazole class'', Bioorganic & Medicinal Chemistry, 16: 4294-4303, (2008). doi: 10.1016/j.bmc.2008.02.077

39. Sandeep N. N., Shreyas S. M., Raju P. K., ''Synthesis of Benzimidazole Derivatives in An Aqueous Media and Reflux Conditions Catalysed by L-Proline at pH-4.2'', International Journal of Research and Analytical Reviews, 6: 485-491, (2019). doi: 10.1729/Journal.21332

40. Heaney H., Ley S. V., ''N-alkylation of indole and pyrroles in dimethyl sulphoxide'', Journal of the Chemical Society Perkin Transactions 1, 4: 499–500, (1973). doi: 10.1039/P19730000499

41. Blois M. S., ''Antioxidant Determinations by the Use of a Stable Free Radical'', Nature, 181: 1199–1200, (1958). doi: 10.1038/1811199a0

42. Burke M. D., Mayer R. T., ''Ethoxyresorufin: direct fluorimetric assay of a microsomal O-dealkylation which is preferentially inducible by 3-methylcholanthrene'', Drug Metabolism and Disposition, 2: 583-588, (1974).

43. Wills E. D., ''Mechanism of lipid peroxide formation in animal tissues'', Biochemical Journal, 99: 667-676 (1966). doi: 10.1042/bj0990667

44. Wills E. D., ''Lipid peroxide formation in microsomes. Relationship of hydroxylation to lipid peroxide formation'', Biochemical Journal, 113: 333-341, (1969). doi: 10.1042/bj1130333

___

Bibtex @araştırma makalesi { politeknik718979, journal = {Politeknik Dergisi}, eissn = {2147-9429}, address = {Gazi Üniversitesi Teknoloji Fakültesi 06500 Teknikokullar - ANKARA}, publisher = {Gazi Üniversitesi}, year = {2021}, volume = {24}, number = {4}, pages = {1699 - 1706}, doi = {10.2339/politeknik.718979}, title = {Synthesis and Antioxidant Properties of New Benzimidazole Derivatives}, key = {cite}, author = {Gümrükçüoğlu, Nurhan} }
APA Gümrükçüoğlu, N. (2021). Synthesis and Antioxidant Properties of New Benzimidazole Derivatives . Politeknik Dergisi , 24 (4) , 1699-1706 . DOI: 10.2339/politeknik.718979
MLA Gümrükçüoğlu, N. "Synthesis and Antioxidant Properties of New Benzimidazole Derivatives" . Politeknik Dergisi 24 (2021 ): 1699-1706 <
Chicago Gümrükçüoğlu, N. "Synthesis and Antioxidant Properties of New Benzimidazole Derivatives". Politeknik Dergisi 24 (2021 ): 1699-1706
RIS TY - JOUR T1 - Synthesis and Antioxidant Properties of New Benzimidazole Derivatives AU - Nurhan Gümrükçüoğlu Y1 - 2021 PY - 2021 N1 - doi: 10.2339/politeknik.718979 DO - 10.2339/politeknik.718979 T2 - Politeknik Dergisi JF - Journal JO - JOR SP - 1699 EP - 1706 VL - 24 IS - 4 SN - -2147-9429 M3 - doi: 10.2339/politeknik.718979 UR - Y2 - 2020 ER -
EndNote %0 Politeknik Dergisi Synthesis and Antioxidant Properties of New Benzimidazole Derivatives %A Nurhan Gümrükçüoğlu %T Synthesis and Antioxidant Properties of New Benzimidazole Derivatives %D 2021 %J Politeknik Dergisi %P -2147-9429 %V 24 %N 4 %R doi: 10.2339/politeknik.718979 %U 10.2339/politeknik.718979
ISNAD Gümrükçüoğlu, Nurhan . "Synthesis and Antioxidant Properties of New Benzimidazole Derivatives". Politeknik Dergisi 24 / 4 (Aralık 2021): 1699-1706 .
AMA Gümrükçüoğlu N. Synthesis and Antioxidant Properties of New Benzimidazole Derivatives. Politeknik Dergisi. 2021; 24(4): 1699-1706.
Vancouver Gümrükçüoğlu N. Synthesis and Antioxidant Properties of New Benzimidazole Derivatives. Politeknik Dergisi. 2021; 24(4): 1699-1706.
IEEE N. Gümrükçüoğlu , "Synthesis and Antioxidant Properties of New Benzimidazole Derivatives", Politeknik Dergisi, c. 24, sayı. 4, ss. 1699-1706, Ara. 2021, doi:10.2339/politeknik.718979