Novel 2-mercaptobenzimidazole derivatives: synthesis and evaluation of its antibacterial and antioxidant activities
AbstractIn the present study, a series of novel 2-mercapto-benzimidazolium were synthesized from 2-mercapto-benzimidazole with hydrocarbon chains. All compounds obtained are reported for the first time, and the structures of these compounds were confirmed by means of 1H-NMR, 13C-NMR and mass spectrometry. The newly synthesized compounds were subjected to in vitro biological evaluation. The antibacterial activity was evaluated will diffusion assay and density optic method. The antioxidant activity was carried out using DPPH free radical scavenging assay. The result indicated that some compounds show convincing antibacterial activities against two microorganisms: Escherichia coli and Staphylococcus aureus. While, these molecules have not shown interesting antioxidant effects.
- A. Ts. Mavrova, D. Yancheva, N. Anastassova, K. Anichina, J. Zvezdanovic, A. Djordjevic, D. Markovic, A. Smelcerovic, Synthesis, electronic properties, antioxidant and antibacterial activity of some new benzimidazoles, Bioorganic & Medicinal Chemistry, 2015, 23, 19, 6317-6326.
- M. Andrzejewska, L. Yepez-Mulia, A. Tapia, R. Cedillo-Rivera, A. E. Laudy, B. J. Staro´sciak, Z. Kazimierczuk, Synthesis, and antiprotozoal and antibacterial activities of S-substituted 4,6-dibromo- and 4,6-dichloro-2-mercaptobenzimidazoles, European Journal of Pharmaceutical Sciences, 2004, 21, 323-329.
- K. K. Sumayya, V. K. Kamalabhai Amma, G. Babu, C. R Biju, Synthesis, Characterization and Antioxidant studies of 2-Benzylthio benzimidazole derivatives, Int. J. Chem. Pharm. Sci, 2013, 1, 3, 193-198.
- K. Anandarajagopal, R. N. Tiwari, K.G. Bothara, J. A. Jeba Sunilson, C. Dineshkumar, P. Promwichit, 2-Mercaptobenzimidazole Derivatives: Synthesis and Anticonvulsant Activity, Advances in Applied Science Research, 2010, 1, 2, 132-138.
- M. V. De Almeida, S. H. Cardoso, J. V. De Assis, M. V. N. De Souza, Synthesis of 2-mercapto-benzothiazole and 2-mercaptobenzimidazole derivatives condensed with carbohydrates as a potential antimicrobial agents, J. Sulfur,Chem., 2007, 28, 17-22.
- M. Mor, F. Bordi, C. Silva, S. Rivara, V. Zuliani, F. Vacondio, M. Rivara, E. Barocelli,
- S. Bertoni, V. Ballabeni, F. Magnanini, M. Impicciatore, P. Vincenzo Plazzi, Synthesis, biological activity, QSAR and QSPR study of 2-aminobenzimidazole derivatives as potent H3-antagonists, Bioory, Med. Chem., 2004, 12, 4, 663-674.
- E. V. Bakhareva, M.G. Voronkov, M. S. Sorokin, V. A. Lopyrev, S. B. Seredenin, G. M. Gaidarov, Synthesis and neurotropic properties of 2-(carboxymethylthio) derivatives of benzimidazole, benzothiazole and their ammonium salts, Pharm. Chem. J., 1996, 30, 2, 89-91.
- A.Anand, M. V. Kulkarni, S. D. Joshi, S. R. Dixit, One pot Click chemistry: A three component reaction for the synthesis of 2-mercaptobenzimidazole linked coumarinyl triazoles as anti-tubercular agents, Bioorganic & Medicinal Chemistry Letters, 2016, 26, 4709-4713.
- K. Anandarajagopal, R. N. Tiwari, N. Venkateshan, G. V. Pooshan, P. Promwichit, Synthesis and characterization of 2-mercaptobenzimidazole derivatives as potential analgesic agents, J. Chem. Pharm. Res., 2010, 2, 3, 230-236.
- T. L. Rebstock, C. D. Ball, C. L. Hamner, H. M. Sell, Inhibition of Plant Growth by 2-Mercapto-benzimidazole Analogs, Plant physiology, 1955, 30, 4, 382-384.
- B. Zhong, Z. Jia, Y. Luo, B. Guo, D. Jia, Preparation of halloysite nanotubes supported 2-mercaptobenzimidazole and its application in natural rubber, Composites: Part A, 2015, 73, 63-71.
- L. El Ouasif, I. Merimi, H. Zarrok, M. El ghoul, R. Achour, M. Guenbour, H. Oudda, F. El-Hajjaji, B. Hammouti, Synthesis and inhibition study of carbon steel corrosion in hydrochloric acid of a new surfactant derived from 2-mercaptobenzimidazole, J. Mater. Environ. Sci., 2016, 7, 8, 2718-2730.
- M.Th. Makhlouf, S.A. El-Shatory, A. El-Said, The synergistic effect of halide ions and some selected thiols as a combined corrosion inhibitor for pickling of mild steel in sulphuric acid solution, Mater. Chem. Phys., 1996, 43, 1, 76-82.
- S. A. M. Refaey, F. Taha, A. M. Abd El-Malak, Corrosion and Inhibition of 316L stainless steel in neutral medium by 2-Mercaptobenzimidazole, Int. J. Electrochem. Sci., 2006, 1, 80-91.
- Wang, L., Evaluation of 2-mercaptobenzimidazole as corrosion inhibitor for mild steel in phosphoric acid, Corros. Sci., 2001, 43, 12, 2281.
- Lin Wang, J.-X. Pu, H.-C. Luo, Corrosion inhibition of zinc in phosphoric acid solution by 2-mercapto-benzimidazole, Corros. Sci., 2003, 45, 4, 677-683.
- M. C. Costache, M. J. Heidecker, E. Manias, R. K. Gupta, C. A. Wilkie, Benzimidazolium surfactants for modification of clays for use with styrenic polymers, Polymer Degradation and Stability, 2007, 92, 10, 1753-1762.
- M. El Achaby, H. Ennajih, F.Z. Arrakhiz, A. El Kadib, R. Bouhfid, E. Essassi, A. Qaiss, Modification of montmorillonite by novel geminal benzimidazolium surfactant and its use for the preparation of polymer organoclay nanocomposites, Composites: Part B, 2013, 51, 310-317.
- G. Cai, J.Feng, J. Zhu, C. A. Wilkie, Polystyrene- and poly (methyl methacrylate)-organoclay nanocomposites using a one-chain benzimidazolium surfactant, Polymer Degradation and Stability, 2014, 99, 204-210.
- S. Ramkumar, K.-G. Upul Wijayantha, D. Velayutham, S. Anandan, Synthesis of 1, 3-dihexyl-2-(phenylthio)-1H-benzo[d]imidazol-3-ium iodide-A new ionic liquid for dye sensitized solar cell applications, Journal of Molecular Liquids, 2014,193, 185-188.
- N. N. Al-Mohammed, R. S. Duali Hussen, T. Hussein Ali, Y. Alias, Z. Abdullah, Tetrakis-imidazolium and benzimidazolium ionic liquids: a new class of biodegradable surfactants, RSC Adv., 2015, 5, 21865-21876.
- A. El Kadib, E. Essassi, R. Bouhfid, H. Ennajih, Préparation de nouveaux bio-composites chitosan-argile modifiée, N° brevet MA34933 B1, 01.03, 2014.
- A. K. Lal, M. D. Milton, Synthesis of new benzimidazolium salts with tunable emission intensities and their application as fluorescent probes for Fe3+ in pure aqueous media, Tetrahedron Letters, 2014, 55, 10, 1810-1814.
- M. Bousmina, E. Essassi, R. Bouhfid, H. Ennajih, Surfactants pour la modification d'argile, méthode de synthèse et les nanocomposites produits, N° brevet WO 2012/011793 A1, 26.01, 2012.
- A. Bouyahya, J. Abrini, EO. Khay, S.Charfi, N. Boujida, A. EL Harsal, A. Talbaoui, A. ET-Touys, Y. Bakri, N. Dakka, In vitro Antibacterial Activity of Organic Extracts from North-West Moroccan Medicinal Plant Myrtus communis (L.)., Biotechnology Journal International, 2016 a , 16, 1-9.
- A. Bouyahya, J. Abrini, A. El-Baabou, Y. Bakri, N. Dakka, Determination of phenol content and antibacterial activity of five medicinal plants ethanolic extracts from North-West of Morocco, J Plant Pathol Microbiol, 2016 c, 7, 107-111.
- G.J. Kaur, D.S. Arora, Antibacterial and phytochemical screening of Anethum graveolens, Foeniculum vulgare and Trachysprmum ammi, BMC Complement Altern Med, 2009, 6, 9-30.
- P. Skandamis, K. Koutsoumanis, K. Fasseas, G.J.E. Nychas, Inhibition of oregano essential oil and EDTA on E. coli O157: H7, Italian Journal of Food Science, 2001,13, 65-75.
- S. Bouhdid, J. Abrini, M. Amensour, A. Zhiri, M. J. Espung, A. Manresa, Functional and ultrastructural changes in Pseudomonas aeruginosa and Staphylococcus aureus cells induced by Origanum compactum essential oil, Journal of Applied Microbiology, 2009, 106, 1558-1568.
- S. Bouhdid, J. Abrini, M. Amensour, A. Zhiri, M. J. Espung, A. Manresa, Functional and ultrastructural changes in Pseudomonas aeruginosa and Staphylococcus aureus cells induced by Cinnamomum verum essential oil, Journal of Applied Microbiology, 2010, 109, 1139-1149.
- H. Barakat, Composition, Antioxidant, Antibacterial Activities and Mode of Action of Clove (Syzygium aromaticum L.) Buds Essential Oil, Journal of Applied Science & Technology, 2014, 4, 1934-1951.
- B.D. Oliveira, A.C. Rodrigues, BMI Cardoso, A.L.C.C. Ramos, M.C. Bertoldi, J.G. Jason Guy Taylor, L.R. Luciana da Cunha, U.M. Pinto, Antioxidant, antimicrobial and anti-quorum sensing activities of Rubusrosaefolius phenolic extract, Industrial Crops and Products, 2016, 84, 59-66.
- K. Myszka, M.T. Schmidt, M. Majcher, W. Juzwa, M. Olkowicz, K. Czaczyk., Inhibition of quorum sensing-related biofilm of Pseudomonas fluorescens KM121 by Thymus vulgare essential oil and its major bioactive compounds., International Biodeterioration & Biodegradation, 2016, 114, 252-259.
- A. Luas, A. Duarte, J. Gominho, F. Domingues, A.P. Duarte, Chemical composition, antioxidant, antibacterial and anti-quorum sensing activities of Eucalyptus globulus and Eucalyptus radiata essential oils, Industrial Crops and Products, 2016, 79, 274-282.
- K. Parikh, D. Joshi, Antibacterial and antifungal screening of newly synthesized benzimidazole-clubbed chalcone derivatives, Med. Chem. Res., 2013, 22, 3688-3697.
- F.D. Lowy, Antimicrobial resistance: the example of Staphylococcus aureus, J. Clin. Invest., 2003, 111, 9, 1265-1273.
- A. Pantosti, A. Sanchini, M. Moaco, Mechanisms of antibiotic resistance in Staphylococcus aureus, Future Microbiol., 2007, 2, 3, 323-340.
- K. Hiramatsu, L. Cui, M. Kuroda, T. Ito, The emergence and evolution of methicillin-resistant Staphylococcus aureus, Trends Microbiol., 2001, 9, 486-493.
- V. Bondet, W. Brand-Williams, C. Berset, Kinetics and mechanisms of antioxidant activity using the DPPH free radical method, LWT-Food Sci. Technol, 1997, 30, 609-615.
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (SeeÂ The Effect of Open Access).