Synthesis and Antimicrobial Activity of New Benzimidazole derivatives Bearing Five-Membered Heterocyclic Moieties

Ammar Ferman Abbood, Ahmed M. Abdula, Ghosoun Laftaa Mohsen, Younis Baqi

Abstract


A new series of 2-substituted-1H-benzimidazol as potentially antimicrobial agents were designed, synthesized and characterized by IR, 1H-NMR and Mass spectra. The synthesized compounds were in vitro screened against Escherichia coli, Klebsiella spp. (gram negative), Staphylococcus aureus, Staphylococcus epidermidis (gram positive) as well as Candida albicans. The in vitro biological evaluation revealed that some of the target compounds exerted good antimicrobial activity. Noticeably, compound 11 exhibited promising activity against Staphylococcus aureus and Klebseilla SPP at 1 mg/mL concentration.


Keywords


benzimidazol, pyrazoline, isoxazoline, antimicrobial

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References


World Health Organization. (‎2017)‎. Prioritization of pathogens to guide discovery, research and development of new antibiotics for drug-resistant bacterial infections, including tuberculosis. World Health Organization. https://apps.who.int/iris/handle/10665/31182.

S. R. Palumbi, Science 2001, 293, 1786-1790.

CrossRef | PubMed

Tacconelli E, Carrara E, Savoldi A, Harbarth S, Mendelson M, Monnet DL, Pulcini C, Kahlmeter G, Kluytmans J, Carmeli Y, Ouellette M, Outterson K, Patel J, Cavaleri M, Cox EM, Houchens CR, Grayson ML, Hansen P, Singh N, Theuretzbacher U, Magrini N; WHO Pathogens Priority List Working Group. Discovery, research, and development of new antibiotics: the WHO priority list of antibiotic-resistant bacteria and tuberculosis. Lancet Infect Dis. 2018;18:318-327.

CrossRef

Fei F, Zhou ZM. New substituted benzimidazole derivatives: a patent review (2010-2012). Expert Opin Ther Pat 2014;23:1157-1179.

CrossRef | PubMed

Kamal Shah , Sumit Chhabra , Sushant K. Shrivastava and Pradeep Mishra .Benzimidazole: a promising pharmacophore. Med Chem Res 2013;22:5077-5104.

CrossRef

Valdez J., Cedillo R., A. Hernandez-Campos, Yepez L., Hernandez-Luis F., Navarrete-Vazquez G., Tapia A., Cortes R., Hernandezc M., Castilloa R. (2002) Synthesis and antiparasitic activity of 1H-benzimidazole derivatives. Bioorg Med Chem Lett; 12: 2221-2224.

CrossRef

Xue-Jie Fang, Ponmani Jeyakkumar , Srinivasa Rao Avula , Qian Zhou, Cheng-He Zhou. Design, synthesis and biological evaluation of 5-fluorouracil-derived benzimidazoles as novel type of potential antimicrobial agents. Bioorg Med Chem Lett 2016;26(11):2584-2588.

CrossRef | PubMed

Ates-Alagoz Z. Antimicrobial Activities of 1-H-Benzimidazole-based Molecules. Curr Top Med Chem. 2016;16:2953-2962.

CrossRef | PubMed

Vasava MS, Bhoi MN, Rathwa SK, Jethava DJ, Acharya PT, Patel DB, Patel HD. Benzimidazole: A Milestone in the Field of Medicinal Chemistry. Mini Rev Med Chem. 2020;20:532-565.

CrossRef | PubMed

Song D and Ma S. Recent Development of Benzimidazole-Containing Antibacterial Agents. ChemMedChem. 2016, 11(7):646-659.

CrossRef | PubMed

Monika Gaba , Sarbjot Singh and Chander Mohan. Benzimidazole: An emerging scaffold for analgesic and anti-inflammatory agents. European Journal of Medicinal Chemistry 76 (2014) 494-505.

CrossRef | PubMed

Mohd Rashid, Asif Husain and Ravinesh Mishra. Synthesis of benzimidazoles bearing oxadiazole nucleus as anticancer agents. Eur. J. Med. Chem. 2012, 54, 855-866.

CrossRef | PubMed

Zafar Saied Saify , M Kamran Azim, Waseem Ahmad, Mehrun Nisa, Daniel E Goldberg, Shaheen A Hussain, Shamim Akhtar, Arfa Akram, Arshad Arayne, Anna Oksman, Ishtiaq A Khan. New benzimidazole derivatives as antiplasmodial agents and plasmepsin inhibitors: synthesis and analysis of structure-activity relationships. Bioorg Med Chem Lett 2012 Jan 15;22(2):1282-1286.

CrossRef | PubMed

HéctorTorres-Gómeza, EmanuelHernández-Núñez,IsmaelLeón-Rivera, JorgeGuerrero-Alvarez, RobertoCedillo-Rivera, RosaMoo-Puc, RocíoArgotte-Ramos, María delCarmen Rodríguez-Gutiérrez, Manuel JesúsChan-Bacab and GabrielNavarrete-Vázquez. Design, synthesis and in vitro antiprotozoal activity of benzimidazole-pentamidine hybrids. 18( 11). 2008, : 3147-3151.

CrossRef | PubMed

Anthony R. Porcari, Rodrigo V. Devivar, Louis S. Kucera, John C. Drach, and Leroy B. Townsend. Design, Synthesis, and Antiviral Evaluations of 1-(Substituted benzyl)-2-substituted-5,6-dichlorobenzimidazoles as Nonnucleoside Analogues of 2,5,6-Trichloro-1-(â-D-ribofuranosyl)benzimidazole. J. Med. Chem. 1998, 41(8):1252-1262.

CrossRef | PubMed

Yogita Bansal, Om Silakari. The therapeutic journey of benzimidazoles: A review. Bioorg. Med. Chem. 20 (2012) 6208-6236.

CrossRef | PubMed

Ghosoun Laftaa Mohsen, Ahmed Mutanabbi Abdula and Abdulkadir Mohammed Noori Jassim. Synthesis, Antimicrobial, Antioxidant and Docking Study of Novel Isoxazoline Derivatives. 2018, ACTA Pharmaceutica Sciencia 56(3):71-83.

CrossRef

Krushnkumar Karangiya and Jatin Upadhyay. Synthesis and Antimicrobial Screening of New Pyrazolines Derived From Chalcones of Vanillin Analog. Int. J. Pharm. Sci. Drug Res.2016; 8(2): 98-102.

CrossRef

Marwa H. Ahmed, Maher A. El-Hashash, Magda I. Marzouk and Abeer M. El-Naggar. Design, Synthesis, and Biological Evaluation of Novel Pyrazole, Oxazole, and Pyridine Derivatives as Potential Anticancer Agents Using Mixed Chalcone. J. Heterocyclic Chem.2019 56(1): 114-123

CrossRef

Jaseela Majeed and M. Shaharyar. Synthesis and in vivo diuretic activity of some novel pyrimidine derivatives. Journal of Enzyme Inhibition and Medicinal Chemistry, 2011; 26(6): 819-826.

CrossRef | PubMed

Kenan Buldurun , Nevin Turan , Ahmet Savcı , Naki Colak. Synthesis, structural characterization and biological activities of metal(II) complexes with Schiff bases derived from 5-bromosalicylaldehyde: Ru(II) complexes transfer hydrogenation. J. Saudi Chem. Soc., 2019. 23(2):205-214.

CrossRef

Ganapathi E , Madhu S, Chatterjee T, Gonnade R, Ravikanth M, 2014. Synthesis, Structure, Spectral, Electrochemical and Sensing Properties of 3-Amino Boron-Dipyrromethene and Its Derivatives. Dyes and Pigments. 102 (2014) 218-227.

CrossRef

Raghavendra N M, Thampi P, Gurubasavarajaswamy P M and Sriram D, 2007. Synthesis and Antimicrobial Activities of Some Novel Substituted 2-Imidazolyl-N-(4-oxo-quinazolin-3(4H)-yl)-acetamides. Chem. Pharm. Bull. 55(11) 1615-1619.

CrossRef | PubMed

Paola Vicini, Athina Geronikaki, Kitka Anastasia, Matteo Incerti, Franca Zani, Synthesis and antimicrobial activity of novel 2-thiazolylimino-5-arylidene-4-thiazolidinones. Bioorg Med Chem..2006;14(11):3859-3864.

CrossRef | PubMed

Abid S E , Abdula A M , Al Marjani M F and Abdulhameed Q M. 2019. Synthesis, Antimicrobial, Antioxidant and Docking Study of Some Novel 3,5- Disubstituted- 4,5- dihydro- 1H- pyrazoles Incorporating Imine Moiety. Egypt.J.Chem. 62( 4):1139-1149.

CrossRef

Kenneth A. Savin, in Writing Reaction Mechanisms in Organic Chemistry (Third Edition), 2014.

CrossRef




DOI: http://dx.doi.org/10.23851/mjs.v32i4.992

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