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Letters in Drug Design & Discovery

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ISSN (Print): 1570-1808
ISSN (Online): 1875-628X

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Research Article

Synthesis, Antioxidant and Antiurease Activities of Some New 5,6- dichloro-2-(4-fluorobenzyl)-1H-benzimidazole Derivatives Containing Furan, Oxadiazole, Triazole and Thiadiazole Moieties

Author(s): Hakan Bektas*, Canan Albay, Emre Menteşe, Bahar Bilgin Sokmen, Zafer Kurt and Dilem Şen

Volume 16, Issue 8, 2019

Page: [939 - 947] Pages: 9

DOI: 10.2174/1570180815666180827124956

Price: $65

Abstract

Background: Benzimidazoles and its derivatives have been attracting interest for many years because of their biological activities. Benzimidazoles containing different heterocyclic moieties have wide range of biological activities such as antimicrobial, antioxidant, anticancer, antiviral, etc.

Methods: In this study, some benzimidazole derivatives containing furan, oxadiazole, triazole and thiadiazole moieties have been synthesized and then evaluated for their antioxidant and antiurease activities.

Results: The results showed that all the tested benzimidazoles indicated remarkable urease inhibitory potentials with IC50 values ranging between 0.303±0.03 to 0.591±0.08 µM.

Conclusion: In conclusion, synthesized benzimidazole derivatives showed good antioxidant and antiurease activities. Heterocyclic groups on benzimidazole nucleus enhance the activities.

Keywords: Antioxidant, antiurease, benzimidazole, 1, 3, 4-oxadiazole, 1, 2, 4-triazole, 1, 3, 4-thiadiazole.

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[1]
Kus, C.; Ayhan-Kılcıgil, G.; Can-Eke, B.; Iscan, M. Synthesis and antioxidant properties of some novel benzimidazole derivatives on lipid peroxidation in the rat liver. Arch. Pharm. Res., 2004, 27, 156-163.
[2]
Ayhan-Kılcıgil, G.; Kus, C.; Coban, T.; Can-Eke, B.; Iscan, M. Synthesis and antioxidant properties of novel benzimidazole derivatives. J. Enzyme Inhib. Med. Chem., 2004, 19, 129-135.
[3]
Zerner, B. Recent advances in the chemistry of an old enzyme, urease. Bioorg. Chem., 1991, 19, 116-131.
[4]
Krajewska, B. Ureases: Roles, properties and catalysis. Wiad Chem., 2002, 56, 223-253.
[5]
Ligabue-Braun, R.; Andreis, F.C.; Verli, H.; Carlini, C.R. 3-to-1: Unraveling structural transitions in ureases. Naturwissenschaften, 2013, 100(5), 459-467.
[6]
Mobley, H.L.; Island, M.D.; Hausinger, R.P. Molecular biology of microbial ureases. Microbiol. Rev., 1995, 59(3), 451-480.
[7]
Sipponen, P.; Hyvärinen, H. Role of Helicobacter pylori in the pathogenesis of gastritis, peptic ulcer and gastric cancer. Scand. J. Gastroenterol., 2009, 3-6.
[8]
Amtul, Z.; Rahman, A.U.; Siddiqui, R.A.; Choudhary, M.I. Chemistry and mechanism of urease inhibition. Curr. Med. Chem., 2002, 9(14), 1323-1348.
[9]
Velík, Y.; Baliharová, J.; Fink-Gremmels, V.; Bull, J.; Lamka, S.; Skálová, J.L. Benzimidazole drugs and modulation of biotransformation enzymes. Res. Vet. Sci., 2004, 76(2), 95-108.
[10]
Kosikowska, P.; Berlicki, L. Urease inhibitors as potential drugs for gastric and urinary tract infections: A patent review. Expert Opin. Ther. Pat., 2011, 21(6), 945-957.
[11]
Spasov, A.A.; Yozhitsa, I.N.; Bugaeva, L.I.; Anisimova, V.A. Benzimidazole derivatives: Spectrum of pharmacological activity and toxicological properties (a review). Pharm. Chem. J., 1999, 33, 232-243.
[12]
Bhattacharya, S.; Chaudhuri, P. Medical implications of benzimidazole derivatives as drugs designed for targeting DNA and DNA associated processes. Curr. Med. Chem., 2008, 15, 1762-1777.
[13]
Khokra, S.L.; Choudhary, D. Benzimidazole an important scaffold in drug discovery. Asian J. Biochem. Pharm. Res., 2011, 3(1), 476-486.
[14]
Ayhan-Kilcigil, G.; Kus, C.; Ozdamar, E.D.; Can-Eke, B.; Iscan, M. Synthesis and antioxidant capacities of some new benzimidazole derivatives. Arch. Pharm. , 2007, 340(11), 607-611.
[15]
Sharma, D.; Narasimhan, B.; Kumar, P.; Judge, V.; Narang, R.; Clercq, E.D.; Balzarini, Ö. Synthesis, antimicrobial and antiviral activity of substituted benzimidazoles. J. Enzyme Inhib. Med. Chem., 2009, 24(5), 1161-1168.
[16]
Abonia, R.; Cortes, E.; Insuasty, B.; Quiroga, J.; Nogueras, M. Cobo, Synthesis of novel 1, 2, 5-trisubstituted benzimidazoles as potential antitumor agents. J. Eur. J. Med. Chem., 2011, 46(9), 4062-4070.
[17]
Srivastava, S.K.; Srivastava, S.; Srivastava, S.D. Synthesis of new 1, 2, 4-triazolo-thiadiazoles and its 2-oxoazetidines as antimicrobial, anticonvulsant and anti-inflammatory agents. Ind. J. Chem. Sect., 2002, 41B(11), 2357-2363.
[18]
Holla, B.S.; Rao, B.S.; Sarojini, B.K.; Akberali, P.M.; Kumari, N.S. Synthesis and studies on some new fluorine containing triazolothiadiazines as possible antibacterial, antifungal and anticancer agents. Eur. J. Med. Chem., 2006, 41(5), 657-663.
[19]
Bhandari, S.V.; Bothara, K.G.; Raut, M.K.; Patil, A.A.; Sarkate, A.P.; Mokale, V.J. Design, synthesis and evaluation of antiinflammatory, analgesic and ulcerogenicity studies of novel s-substituted phenacyl-1, 3, 4-oxadiazole-2-thiol and schiff bases of diclofenac acid as nonulcerogenic derivatives. Bioorg. Med. Chem., 2008, 16(4), 1822-1831.
[20]
Menteşe, E.; Karaali, N.; Yilmaz, F.; Ülker, S.; Kahveci, B. Microwave-assisted synthesis and biological evaluation of some benzimidazole derivatives containing a 1, 2, 4-triazol ring. Arch. Pharm. , 2013, 346(7), 556-561.
[21]
Demirayak, S.; Mohsen, A.U.; Karaburun, A.Ç. Synthesis and anticancer and anti-HIV testing of some pyrazino[1, 2-a] benzimidazole derivatives. Eur. J. Med. Chem., 2002, 37(3), 255-260.
[22]
Abdel-Mohsen, H.T.; Ragab, F.A.F.; Ramla, M.M.; El Diwani, H.I.E. Novel benzimidazole-pyrimidine conjugates as potent antitumor agents. Eur. J. Med. Chem., 2010, 45(6), 2336-2344.
[23]
Rice-Evans, C.; Diplock, A.T. Techniques in free radical research. Elsevier Science, 1. Edition, Amsterdam, 1991, 22, 1-290.
[24]
Yin, H.; Xu, L.; Porter, N.A. Free radical lipid peroxidation: Mechanisms and analysis. Chem. Rev., 2011, 111(10), 5944-5972.
[25]
Griffits, H.R.; Lunec, J.; Aruoma, O.I.; Halliwell, B. Moleculer biology of free radicals in human diseases; Oica. Int, 1998, pp. 327-366.
[26]
Andreadou, I.; Tasouli, A.; Bofilis, E.; Chrysselis, M.; Rekka, E.; Tsantili-Kakouliou, A.; Iliodromitis, E.; Siatra, T.; Kremastinos, D.T. Antioxidant activity of novel indole derivatives and protection of the mycardial damage in rabbits. Chem. Pharm. Bull. , 2002, 50, 165-168.
[27]
Brand-Williams, W.; Cuvelier, M.E.; Berset, C. Use of a free radical method to evaluate antioxidant activity LWT-Food Sci. Technol, 1995, 28(1), 25-30.
[28]
Arnao, M.B.; Cano, A.; Acosta, M. The hydrophilic and lipophilic contribution to total antioxidant activity. Food Chem., 2001, 73(2), 239-244.
[29]
Oyaizu, M. Studies on products of browning reactions: Antioxidative activities of products of browning reaction prepared from glucosamine. Japan. J. Nutr., 1986, 44(6), 307-315.
[30]
Van Slyke, D.D.; Archibald, R.M. Manometric, titrimetric and colometric methods for measurements of urease activity. J. Biol. Chem., 1944, 154, 623-642.
[31]
Alam, N.; Hossain, M.; Khali, M.; Moniruzzaman, M.; Sulaiman, S.; Gan, S. High catechin concentrations detected in Withania somnifera (ashwagandha) by high performance liquid chromatography analysis. BMC Complement. Altern. Med., 2011, 11, 65-73.
[32]
Soares, J.R.; Dinis, T.C.; Cunha, A.P.; Almeida, L.M. Antioxidant activities of some extracts of Thymus zygis. Free Radic. Res., 1997, 26, 469-478.
[33]
Leong, L.P.; Shui, G. An investigation of antioxidant capacity of fruits in Singapore markets. Food Chem., 2002, 76, 69-75.
[34]
Arshad, T.; Khan, K.M.; Rasool, N.; Salar, U.; Hussain, S.; Asghar, H.; Ashraf, M.; Wadood, A.; Riaz, M.; Perveen, S.; Taha, M.; Ismail, N.H. 5-Bromo-2-aryl benzimidazole derivatives as non-cytotoxic potential dual inhibitors of a-glucosidase and urease enzymes. Bioorg. Chem., 2017, 72, 21-31.

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