Investigating of the Antioxidant Activity of Firstly Synthesized Benzimidazole Derivatives

Yıl 2017, , 87 - 95, 15.12.2017

Bahar Bilgin Sökmen , Tuğba Serter Demet Çakır Hakan Bektaş

https://doi.org/10.31466/kfbd.317706

Cited By: 2

Öz

Antioxidant is a defence mechanism in thehuman body preventing the
occurence of oxygen types and the damage generated by them. They are used for
neutralizing free radicals. The presence of antioxidants activity indicates the
presence of the defense mechanism against the various diseases in the human
body. In
this study, activities of for the first time synthesized benzimidazole
compounds antioxidant activities are investigated spectrophotometrically. The
antioxidant activities of benzimidazole derivatives were investigated by
different antioxidant tests such as DPPH radical scavenging activity, ABTS
radical scavenging activity and reducing power. All results were compared with
synthetic antioxidants such as BHT and Trolox. As the
result of the study, antioxidant activity level of the compounds especially 2, 5, 6a, 6b and 7b which are benzimidazole derivatives are found higher extent too
there compounds.

Anahtar Kelimeler

Benzimidazole Derivatives, Antioxidant, DPPH Activity, ABTS Activity

İlk Defa Sentezlenen Benzimidazol Türevlerinin Antioksidan Aktivitesinin İncelenmesi

Öz

Antioksidanlar, reaktif oksijen türlerinin oluşumunu ve bunların meydana
getirdiği hasarı önlemek için vücutta bulunan savunma mekanizmalarıdır. Serbest
radikalleri nötralize etmek için kullanılırlar. Antioksidan aktivitesinin
varlığı, vücutta meydana gelebilecek çeşitli hastalıklara karşı savunma mekanizmasının
var olduğunu göstermektedir. Bu çalışmada, ilk defa sentezlenen benzimidazol
türevlerinin antioksidan aktiviteleri spektrofotometrik olarak incelendi.
Benzimidazol türevlerinin antioksidan aktiviteleri, DPPH, ABTS radikal giderme
aktivitesi ve indirgeme gücü gibi çeşitli antioksidan testleri ile tayin
edildi. Elde edilen sonuçlar, BHT ve Troloks gibi sentetik antioksidanlarla
karşılaştırıldı. Yapılan
çalışmalar sonucunda benzimidazol bileşiklerinden
özellikle 2, 5, 6a, 6b ve 7b nolu bileşiklerin antioksidan
aktivite değerleri diğer bileşiklere oranla daha yüksek bulundu.

Anahtar Kelimeler

Benzimidazol Türevleri, Antioksidan Aktivite, DPPH Aktivitesi, ABTS Aktivitesi

Kaynakça

• 1. Alagöz, Z.G., Can-Eke, B., Coban, T., Iscan, M., Büyükbingöl, E. (2004). Antioxidant properties of novel benzimidazole petinoids. Archives of Pharmaceutical Pharma Medicinal Chemistry. 337: 188-192.
• 2. Arnao, M.B., (2000). Some methodological problems in the determination of antioxidant activity using chromogen radicals. A practical case. Trends in Food Science and Technology. 11: 419-421.
• 3. Baltaş, N., Menteşe, E., Pakyıldız, S., Yılmaz, F. (2015, Mart). Yeni benzimidazol türevi bileşiklerin sentezi, antioksidan özellikleri ve klinik öneme sahip bazı enzimler üzerine inhibisyon etkilerinin incelenmesi. 3.İlaç Kimyası: İlaç Etkin Maddesi Tasarımı, Sentezi, Üretimi ve Standardizasyonu Kongresi, Rize- TURKEY.
• 4. Blois, M. S. (1958). Antioxidant determinations by the use of a stable free radical. Nature, 26: 1119-1200.
• 5. Brand-Williams, W., Cuvelier, M.E., Berset, C. (1995). Use of a free radical method to evaluate antioxidant acitivity, Lebensmittel-Wissenschaft und-Technologie/Food Science and Technolog, 28: 25-30.
• 6. Chakrabarty, M., Karmakar, S., Mukherji, A., Arima, S., Harigaya, Y. (2006). Application of sulfamic acid as an eco-friendly catalyst in an expedient synthesis of benzimidazoles. Heterocycles. 68: 967-974.
• 7. Eş, S. (2013).İlk defa sentezlenen 1,2,4-triazol schiff bazı bileşiklerininantioksidan, anti-elastaz ve anti-tirozinaz aktivitelerinin incelenmesi. Giresun Üniversitesi, Fen Bilimleri Enstitüsü, Yüksek Lisans Tezi, pp. 92, Giresun.
• 8. Foye, W.O. (1995). Cancer Chemotherapeutic Agents. American Chemical Society. 1-212.
• 9. Demirayak, S., Kayagil, I., Yurttas, L. (2011). Microwave supported synthesis of some novel 1,3-diarylpyrazino[1,2-a]benzimidazol derivatives and investigation of their anticancer activities. European Journal of Medicinal Chemistry, 46 (1): 411-416.
• 10. Going, C.J., Mayer, V.W. (1995). Induction of chromosome loss in saccharomyces cerevisiae strain D61.M by selected benzimidazole compounds. Mutation Research. 343: 185-199.
• 11. Habernickel, V.J. (1992). Alkyl-5-heterocyclic-benzimidazolyl-carbamate derivatives. Drugs made in Germany, 35: 97.
• 12. Hemalatha, S., Ayyappan, T., Shanmugam, S., Nagavalli, S., Kurubha, T.S. (2006). evaluation of antidiabetic and diuretic activity of polyherbal formulation. Indian Journal of Trade Knowledge. 5: 468-470.
• 13. Kasnak, C., Palamutoğlu, R. (2015). Doğal antioksidanların sınıflandırılması ve insan sağlığına etkileri. Türk Tarım – Gıda Bilim ve Teknoloji Dergisi, 3: 226-234.
• 14. Kazimierczuk, Z., Upcroft, J.A., Upcroft, P., Gorska, A., Starosciak, B., Agnieszka, L. (2002). Synthesis, Antiprotozoal and Antibacterial Activity of Nitro- and Halogeno-Substituted Benzimidazole Derivatives. Acta Biochimica Polonica, 49: 185-195.
• 15. Kerimov, İ. (2011). Bazı yeni oksadiazol benzimidazol türevlerinin sentezi yapılarının aydınlatılması ve antioksidan aktivitelerininin değerlendirilmesi. Ankara Üniversitesi, Sağlık Bilimleri Enstitüsü, Doktora Tezi, pp. 143, Ankara.
• 16. Keurulainen, L., Salin, O., Siiskonen, A., Kern, J. M., Alvesalo, J., Kiuru, P. and Maass, M. (2010). Design and synthesis of 2-arylbenzimidazoles and evaluation of their inhibitory effect against Chlamydia pneumoniae. Journal of Medicinal Chemistry. 53: 7664-7674.
• 17. Khairnar, V.L., Lokhande, S.R., Khadse, B.G. (1981). Synthesis and antifungal and anti tubercular properties of some benzimidazole derivatives, Chemical Abstract. 95: 203833h.
• 18. Kuba, K., Kohara, Y., Imamiya, E., Sugiura, Y., Inada, Y., Furukawa, Y., Nishikawa, K., Naka, T. (1993). Nonpeptide angiotensin-I receptor antagonists. synthesis and biological activity of benzimidazoles. Journal of Medicinal Chemistry, 36: 2182-2195.
• 19. Kuş, C., Ayhan, K.G., Ozbey, S., Kaynak, F.B., Kaya, M., Coban, T., Can, E.B. (2008). Synthesis and antioxidant properties of novel n-methyl-1,3,4-thiadiazole-2-amino and 4-methyl-2h-1,2,4-triazole-3(4h)-thione derivatives of benzimidazole class. Bioorganic and Medicinal Chemistry, 16: 4294-4303.
• 20. McBride, C. M., Renhowe, P. A., Heise, C., Jansen, J. M., Lapointe, G., Ma, S., Pineda, R., Vora, J., Wiesmann, M., Shafer, C.M. (2006). Design and Structure. Bioorganic & Medicinal Chemistry Letters, 16: 3595-3599.
• 21. Meanwell, N.A., Krystal, M. (2007). Respiratory syncytial virus: the discovery and optimization of orally bioavailable fusion inhibitors. Drugs Future, 32: 441-445.
• 22. Menteşe, E., Bektaş, H., Bilgin Sokmen, B., Emirik, M., Çakır, D., Kahveci, B. (2017). Synthesis and molecular docking study of some 5,6-dichloro-2-cyclopropyl-1h-benzimidazole derivatives bearing triazole, oxadiazole, and imine functionalities as potent inhibitors of urease. Bioorganic & Medicinal Chemistry Letters. 27, 3014-3018.
• 23. Nofal, Z.M., Fahmy, H.H. Mohamed, H.S. (2002). Synthesis, antimicrobial and molluscicidal activities of new benzimidazole derivatives. Archives of Pharmacal Research Journal. 25: 28-38.
• 24. Osman, A.M., Wong, K.K.Y., Fernyhough, A. (2006). ABTS radical driven-oxidation of polyphenols: Isolation and elucidation of covalent adducts, Biochemical and Biophysical Research Communications. 346: 321-329.
• 25. Oyaizu, M. (1986). Studies on products of browning reaction: antioxidative activities of products of browning reaction prepared from glucosamine. Japanese Journal of Nutrition. 44: 307-315.
• 26. Patil, A., Ganguly, S., Surana, S. (2008). A Systematic Review of benzimidazole derivatives as an antiulser agent. Rasayan Journal of Chemistry. 1 (3): 447-460. Ramya, V.S., Kallappa, M.H., Keri, S. (2010). Derivatives of benzimidazole pharmacophore: synthesis anticonvulsant. European Journal of Medicinal Chemistry. 45: 1753-1759.
• 27. Savall, B.M., Edwards, J.P., Venable, J.D., Buzard, D.J., Thurmond, R., Hack, M., McGovern, P. (2010). Agonist/antagonist modulation in a series of 2-aryl benzimidazole h4 receptor ligands. Bioorganic & Medicinal Chemistry Letters, 20: 3367-3371.
• 28. Soares, J.R., Dinis, T.C.P., Cunha, A.P., Almeida, L.M. (1997). Antioxidant activity of some extracts of Thymus zygis. Free Radical Research. 26: 469-478.