Research Journal of Pharmacy and Technology

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Green Chemistry Approach for the Synthesis of Some Benzimidazole Derivatives and their Biological Evaluation


Affiliations
1 Department of Pharmaceutical Chemistry, SRM College of Pharmacy, SRM Institute of Science and Technology, Kattankulathur, Chennai, India
     

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Microwave induced organic reactions are simple, fast, efficient and an economical method for the synthesis of organic molecules and has developed as a tool towards green chemistry. Microwave assistance can reduce the time of chemical reaction from hours to seconds. Benzimidazole nucleus owing to its wide range of biological activities anticipated to be an important pharmacophore in the modern drug discovery. Benzimidazole nucleus showing biological activities such as anti-convulsant, anti-inflammatory, anti-cancer etc., has made it an imperative anchor for development of modern therapeutic agents. Therefore six derivatives belonging to substituted benzimidazole were synthesized in one step microwave assistance and their structural integrity was confirmed by spectroscopy. The derivatives were evaluated in-vitro for free radical scavenging property, anti-microbial, cytotoxic activities. The free radical scavenging ability of synthesized compounds and standard ascorbic acid were tested using DPPH assay. The synthesized compounds 5(c), 5(d) and 5(f) possessed significant anti-oxidant property. The anti-microbial activity was assessed using two strains of gram positive and gram negative with standard tetracycline and the cytotoxic effect was performed using Brine shrimp lethality assay. Compounds 5(c), 5(d) and 5(f) showed significant anti-microbial action against gram positive and gram negative strains. LD50 was determined by cytotoxic assay using brine shrimp. Compounds 5(d) and 5(f) showed significant activity when compared with that of standard capacetabine. The results bespeak a new potential for benzimidazole derivatives as lead compounds to advance as medicinal agents.

Keywords

Chemistry, Benzimidazoles, Anti-Oxidant, Anti-Microbial, Brine Shrimp Lethality Assay.
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  • Kiumars Bahrami, Mehdi Khodaei M, Fardin Naali. Mild and Highly efficient method for the synthesis of 2-Arylbenzimidazoles and 2-Arylbenzothiazoles. Journal of organic chemistry. 2008; (73):6835–6837.

  • Pranjal Gogoi, Dilip Konwar. An efficient and one pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon-nitrogen binds in water. Tetrahedron letters. 2006; (47):79–82.

  • Jie-Ping Wan,et al. Water mediated chemoselective synthesis of 1, 2-disubstituted benzimidazoles using o-phenylenediamine and the extended synthesis of quinoxalines. Journal of Green Chemistry. 2009; (11): 1633–1637.

  • Kumaraswamy Gullapelli, et al. Synthesis of 1,3,5 triazinane-2-ones and 1,3,5 Oxadiazinane-2-ones linked with benzimidazoles. Asian Journal of Research in Chemistry 2017; 10(4), 0974-4169.

  • Arun B. Chavan, et al. Solvent free U.V-Catalyzed Synthesis of Benzimimdazoles. Asian Journal of Research in Chemistry 2016; 9(10), 0974-4169.

  • Atul R. Bendale,etal. Sonochemical Synthesis of 2, 3-Diphenylquinoxaline Using Different Catalysts, a Green Chemistry Approach. Asian Journal of Research in Chemistry. 2011; 4(6), 0974-4169.

  • C. Thangavelu, et al. Sustainability of Potable Water System: Toward Green Chemistry and Green Technologies. Asian Journal of Research in Chemistry. 2011; 4(7), 0974-4169.

  • Priyanka M. Patel, et al. Green Chemistry -An Overview. Asian Journal of Research in Chemistry 2013; 6(7), 0974-4169.

  • Pankaj Kumar, et al. Synthesis and Antimicrobial evaluation of Some novel Mercapto Pyrimidine via Pyrrole chalcone. Research Journal of Pharmacy and Technology. 2018; 11(7): 0974-3618.

  • Yogita Bansal, Om Silakari. The therapeutic journey of benzimidazoles. Bioorganic & Medicinal Chemistry. 2012; (20): 6208–6236.

  • Rohit Tripathi, et al. Pharmacological activities of Benzimidazole derivatives - An Overview. Asian Journal of Research in Chemistry. 2013; 6(5), 0974-4169.

  • Harti Jaouad, et al. Benzimidaoles and Pharmacological Activities: A Review. Research Journal of Pharmacy and Technology 2014; 7(4), 0974-3618.

  • Priya D, Srimathi R. Synthesis and Characterization of Antimicrobial Activity of Novel Thiazolidinone Derivatives of 1, 2-Benzisoxazole. International Journal of Chem Tech Research. 2016; 9(9): 652-659.

  • Salahuddin, Mohammad Shaharyar, Avijit Mazumder. Benzimidazoles: A biologically active compounds. Arabian Journal of Chemistry. 2017; (10): 157–173.

  • CananKus, 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. 2008; (16): 4294–4303.

  • Muhammad Taha, et al. Synthesis, antiglycation and Antioxidant potentials of Benzimidazole Derivatives. Journal of King Saud University-Science. 2018; (18):1018-3647.

  • Neda O. Anastassova, et al. Design, synthesis, antioxidant properties and mechanism of action of new N, N′- disubstituted benzimidazole-2-thione hydrazone derivatives. Journal of Molecular Structure. 2018; (18): 30416-2.

  • Priya D, Srimathi R, Anjana G.V. Synthesis and evaluation of some mannich bases of Quinazolinone nucleus. Asian Journal of Pharmaceutical and Clinical Research. 2018; 11(2):407-409.

  • Radha Krishan Arora, et al. Novel coumarin-benzimidazole derivatives as anti-oxidants and safer anti-inflammatory agents. Acta Pharmaceutica Sinica B. 2014; 4(5): 368-375.

  • Anelia Ts. Mavrova, et al. Synthesis, electronic properties, antioxidant and antibacterial activity of some new benzimidazoles. Bioorganic & Medicinal Chemistry. 2015; (15): 30010-9.

  • Xia-Bing Fu, et al. Cu (II)–dipeptide complexes of 2-(4′-thiazolyl) benzimidazole: Synthesis, DNA oxidative damage, antioxidant and in vitro antitumor activity. Journal of Inorganic Biochemistry. 2015; (143): 77–87.

  • Lincy Joseph; Mathew George. Analgesic and Anti-Oxidant Activities of Certain (E)-3 Arylidene Flavanones Synthesized by One Pot Method. Asian Journal of Research in Chemistry 2009; 2(3), 0974-4169.

  • Prashant N. Ubale; Sambhaji P. Vartale; Sandip G. Sontakke. Synthesis and anti-oxidant activity of some new substituted pyrazolo [ 4,5-e]-4H pyrimido[2,3-b] benzimidazoles. Asian Journal of Research in Chemistry 2016; 9(10), 0974-4169.

  • Ya-Nan Wang, et al. Novel purine benzimidazoles as anti-microbial agents by regulating ROS generation and targeting clinically resistant Staphalococcus aureus DNA groove. Bioorganic and Medicinal Chemistry letters. 2018; (28):1621-1628.

  • Snehlata Yadav, et al. Synthesis and evaluation of antimicrobial, antitubercular and anticancer activities of benzimidazole derivatives. Egyptian Journal of Basic and Applied Sciences. 2017.

  • El-Gohary N S, Shaaban M I. Synthesis, antimicrobial, antiquorum-sensing and antitumor activities of new benzimidazole analogs. European Journal of Medicinal Chemistry. 2017; (17): 30435.

  • Desai N C, et al. Synthesis, antibacterial and antitubercular activities of benzimidazole bearing substituted 2-pyridone motifs. European Journal of Medicinal Chemistry. 2014; (14): 00522-4.

  • Xue-Jie Fang, et al. Synthesis and biological evaluation of 5-fluorouracil-derived benzimidazoles as novel type of potential antimicrobial agents. Bioorganic & Medicinal Chemistry Letters. 2016; (16): 30410-3.

  • Sujit Kumar Mohantya, et al. Design, synthesis of novel azo derivatives of benzimidazole as potent antibacterial and anti tubercular agents. Beni-Suef University Journal of Basic and Applied Sciences. 2018;2314-8535.

  • Niggula Praveen Kumar, et al. Synthesis of substituted phenanthrene-9-benzimidazole conjugates: Cytotoxicity evaluation and apoptosis inducing studies. European Journal of Medicinal Chemistry. 2017; (17): 30688-8.

  • Rajan Abraham, et al. A novel series of N-acyl substituted indole-linked benzimidazoles and naphthoimidazoles as potential anti inflammatory, anti biofilm and anti microbial agents. Microbial Pathogenesis. 2017; 17: 31667-4.

  • Mohan Rao Gangula and Vijaya Kumar Baru. Synthesis and Antimicrobial Activity of Some Novel N Mannich Bases of Substituted 2-Mercapto-1H-Benzimidazoles. 2012; 5(10), 0974-4150.

  • Gopi C. and Dhanaraju M. D. Synthesis, Characterization and Anti-Microbial Evaluation of Derivative of Chalcone. Journal of Research in Chemistry 2011; 4(2), 0974-4169.

  • Mohan Rao Gangula; Vijaya Kumar Baru. Synthesis and Antimicrobial Activity of Some Novel N-Mannich Bases of Substituted 2-Mercapto-1H-Benzimidazoles. Asian Journal of Research in Chemistry 2012; 5(10), 0974-4169.

  • Santosh Dighe,et al. Synthesis and Evaluation of Some New Benzimidazole Derivatives for their Anti-Microbial and Anti-Inflammatory Activities. Asian Journal of Research in Chemistry 2014; 7(12), 0974-4169.

  • Pratik P. Maske, et al. Synthesis and evaluation of 5,6-dinitro and 2-dialkylaminosubstituted benzimidazoles derivatives as potential antimicrobial agents. Asian Journal of Research in Chemistry 2015; 8(3), 0974-4169.

  • K. Girija; B. Jamuna. Design and Synthesis of Some Novel Schiff’s Base Aryl Imidazole Derivatives, Characterization, Docking and Study of their Anti-Microbial Activity. Research Journal of Pharmacy and Technology 2015; 8(4), 0974-3618.

  • Elif Apohan, et al. Synthesis, cytotoxic and antimicrobial activities of novel cobalt and zinc complexes of .benzimidazole derivatives. Journal of Organometallic Chemistry. 2016; (16): 30524-1.

  • Seenaiah D, et al. Synthesis, antimicrobial and cytotoxic activities of pyrimidinyl benzoxazole, benzothiazole and benzimidazole. European Journal of Medicinal Chemistry 2014; (77): 1-7.

  • Mirza Feroz Baig, et al. Iodine-catalyzed Csp3-H functionalization of methylhetarenes: One-pot synthesis and cytotoxic evaluation of heteroarenyl-benzimidazoles and benzothiazole. Bioorganic & Medicinal Chemistry Letters. 2017; (17): 30758-8.


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  • Green Chemistry Approach for the Synthesis of Some Benzimidazole Derivatives and their Biological Evaluation

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Authors

M. Kavya
Department of Pharmaceutical Chemistry, SRM College of Pharmacy, SRM Institute of Science and Technology, Kattankulathur, Chennai, India
D. Priya
Department of Pharmaceutical Chemistry, SRM College of Pharmacy, SRM Institute of Science and Technology, Kattankulathur, Chennai, India

Abstract


Microwave induced organic reactions are simple, fast, efficient and an economical method for the synthesis of organic molecules and has developed as a tool towards green chemistry. Microwave assistance can reduce the time of chemical reaction from hours to seconds. Benzimidazole nucleus owing to its wide range of biological activities anticipated to be an important pharmacophore in the modern drug discovery. Benzimidazole nucleus showing biological activities such as anti-convulsant, anti-inflammatory, anti-cancer etc., has made it an imperative anchor for development of modern therapeutic agents. Therefore six derivatives belonging to substituted benzimidazole were synthesized in one step microwave assistance and their structural integrity was confirmed by spectroscopy. The derivatives were evaluated in-vitro for free radical scavenging property, anti-microbial, cytotoxic activities. The free radical scavenging ability of synthesized compounds and standard ascorbic acid were tested using DPPH assay. The synthesized compounds 5(c), 5(d) and 5(f) possessed significant anti-oxidant property. The anti-microbial activity was assessed using two strains of gram positive and gram negative with standard tetracycline and the cytotoxic effect was performed using Brine shrimp lethality assay. Compounds 5(c), 5(d) and 5(f) showed significant anti-microbial action against gram positive and gram negative strains. LD50 was determined by cytotoxic assay using brine shrimp. Compounds 5(d) and 5(f) showed significant activity when compared with that of standard capacetabine. The results bespeak a new potential for benzimidazole derivatives as lead compounds to advance as medicinal agents.

Keywords


Chemistry, Benzimidazoles, Anti-Oxidant, Anti-Microbial, Brine Shrimp Lethality Assay.

References