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Mini-Reviews in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1389-5575
ISSN (Online): 1875-5607

Review Article

Antimicrobial Potential of Benzimidazole Derived Molecules

Author(s): Yogita Bansal*, Manjinder Kaur and Gulshan Bansal

Volume 19, Issue 8, 2019

Page: [624 - 646] Pages: 23

DOI: 10.2174/1389557517666171101104024

Price: $65

Abstract

Structural resemblance of benzimidazole nucleus with purine nucleus in nucleotides makes benzimidazole derivatives attractive ligands to interact with biopolymers of a living system. The most prominent benzimidazole compound in nature is N-ribosyldimethylbenzimidazole, which serves as an axial ligand for cobalt in vitamin B12. This structural similarity prompted medicinal chemists across the globe to synthesize a variety of benzimidazole derivatives and to screen those for various biological activities, such as anticancer, hormone antagonist, antiviral, anti-HIV, anthelmintic, antiprotozoal, antimicrobial, antihypertensive, anti-inflammatory, analgesic, anxiolytic, antiallergic, coagulant, anticoagulant, antioxidant and antidiabetic activities. Hence, benzimidazole nucleus is considered as a privileged structure in drug discovery, and it is exploited by many research groups to develop numerous compounds that are purported to be antimicrobial. Despite a large volume of research in this area, no novel benzimidazole derived compound has emerged as clinically effective antimicrobial drug. In the present review, we have compiled various reports on benzimidazole derived antimicrobials, classified as monosubstituted, disubstituted, trisubstituted and tetrasubstituted benzimidazoles, bisbenzimidazoles, fused-benzimidazoles, and benzimidazole derivative-metal complexes. The purpose is to collate these research reports, and to generate a generalised outlay of benzimidazole derived molecules that can assist the medicinal chemists in selecting appropriate combination of substituents around the nucleus for designing potent antimicrobials.

Keywords: Benzimdiazole, antimicrobial, antifungal, antibacterial, metal complex, structure activity relationship.

Graphical Abstract

[1]
He, Y.; Wu, B.; Yang, J.; Robinson, D.; Risen, L.; Ranken, R.; Swayze, E.E. 2-Piperidin-4-yl-benzimidazoles with broad spectrum antibacterial activities. Bioorg. Med. Chem. Lett., 2003, 13(19), 3253-3256.
[2]
Garuti, L.; Roberti, M.; Malagoli, M.; Rossi, T.; Castelli, M. Synthesis and antiproliferative activity of some benzimidazole-4, 7-dione derivatives. Bioorg. Med. Chem. Lett., 2000, 10(19), 2193-2195.
[3]
Abdel-hafez, A.A.M. Benzimidazole condensed ring systems: New synthesis and antineoplastic activity of substituted 3, 4-dihydro-and 1, 2, 3, 4-tetrahydro-benzo[4,5]imidazo[1,2-a]pyrimidine derivatives. Arch. Pharm. Res., 2007, 30(6), 678-684.
[4]
Demirayak, S.; Mohsen, U.A.; 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.
[5]
White, A.W.; Curtin, N.J.; Eastman, B.W.; Golding, B.T.; Hostomsky, Z.; Kyle, S.; Griffin, R.J. Potentiation of cytotoxic drug activity in human tumour cell lines, by amine-substituted 2-arylbenzimidazole-4-carboxamide PARP-1 inhibitors. Bioorg. Med. Chem. Lett., 2004, 14(10), 2433-2437.
[6]
Sondhi, S.M.; Singh, N.; Kumar, A.; Lozach, O.; Meijer, L. Synthesis, anti-inflammatory, analgesic and kinase (CDK-1, CDK-5 and GSK-3) inhibition activity evaluation of benzimidazole/benzoxazole derivatives and some Schiff’s bases. Bioorg. Med. Chem., 2006, 14(11), 3758-3765.
[7]
Ayhan‐Kilcigil, G.; Kus, C.; Ozdamar, E.D.; Can‐Eke, B.; Iscan, M. Synthesis and antioxidant capacities of some new benzimidazole derivatives. Arch. Der. Pharm., 2007, 340(11), 607-611.
[8]
Kus, C.; Ayhan-Kilcigil, G.; Eke, B.C. Synthesis and antioxidant properties of some novel benzimidazole derivatives on lipid peroxidation in the rat liver. Arch. Pharm. Res., 2004, 27(2), 156-163.
[9]
Ateş-Alagoz, Z.; Kuş, C.; Çoban, T. Synthesis and antioxidant properties of novel benzimidazoles containing substituted indole or 1, 1, 4, 4-tetramethyl-1, 2, 3, 4-tetrahydro-naphthalene fragments. J. Enzyme Inhib. Med. Chem., 2005, 20(4), 325-331.
[10]
Ayhan‐Kilcigil, G.; Kus, C.; Ozdamar, E.D.; Can‐Eke, B.; Iscan, M. Synthesis and antioxidant capacities of some new benzimidazole derivatives. Arch. Der. Pharm., 2007, 340(11), 607-611.
[11]
Vinodkumar, R.; Vaidya, S.D.; Kumar, B.V.S.; Bhise, U.N.; Bhirud, S.B.; Mashelkar, U.C. Synthesis, anti-bacterial, anti-asthmatic and anti-diabetic activities of novel N-substituted-2-(4-phenylethynyl-phenyl)-1H-benzimidazoles and N-substituted 2 [4-(4, 4-dimethyl-thiochroman-6-yl-ethynyl)-phenyl)-1H-benzimidazoles. Eur. J. Med. Chem., 2008, 43(5), 986-995.
[12]
Nakano, H.; Inoue, T.; Kawasaki, N.; Miyataka, H.; Matsumoto, H.; Taguchi, T.; Satoh, T. Synthesis of benzimidazole derivatives as antiallergic agents with 5-lipoxygenase inhibiting action. Chem. Pharm. Bull., 1999, 47(11), 1573-1578.
[13]
Beaulieu, C.; Wang, Z.; Denis, D.; Greig, G.; Lamontagne, S. ONeill, G.; Wang, J. Benzimidazoles as new potent and selective DP antagonists for the treatment of allergic rhinitis. Bioorg. Med. Chem. Lett., 2004, 14(12), 3195-3199.
[14]
Torres-Gomez, H.; Hernandez-Nunez, E.; Leon-Rivera, I.; Guerrero-Alvarez, J.; Cedillo-Rivera, R.; Moo-Puc, R.; Navarrete-Vazquez, G. Design, synthesis and in vitro antiprotozoal activity of benzimidazole-pentamidine hybrids. Bioorg. Med. Chem. Lett., 2008, 18(11), 3147-3151.
[15]
Valdez-Padilla, D.; Rodriguez-Morales, S.; Hernandez-Campos, A.; Hernandez-Luis, F.; Yepez-Mulia, L.; Tapia-Contreras, A.; Castillo, R. Synthesis and antiprotozoal activity of novel 1-methylbenzimidazole derivatives. Bioorg. Med. Chem., 2009, 17(4), 1724-1730.
[16]
Shingalapur, R.V.; Hosamani, K.M.; Keri, R.S.; Hugar, M.H. Derivatives of benzimidazole pharmacophore: Synthesis, anticonvulsant, antidiabetic and DNA cleavage studies. Eur. J. Med. Chem., 2010, 45(5), 1753-1759.
[17]
Orjales, A.; Mosquera, R.; Labeaga, L.; Rodes, R. New 2-piperazinylbenzimidazole derivatives as 5-HT3 antagonists. Synthesis and pharmacological evaluation. J. Med. Chem., 1997, 40(4), 586-593.
[18]
Grimmett, M.R. in: Katritzky, A.R.; Rees, C.W.; Scriven, E.F.V. Compr. Heterocycl. Chem II. Pergamon Press: Oxford, 1996; Vol. 3, pp. 77-220.
[19]
Bansal, Y.; Kaur, M.; Silakari, O. Benzimidazole–ibuprofen/ mesalamine conjugates: Potential candidates for multifactorial diseases. Eur. J. Med. Chem., 2015, 89, 671-682.
[20]
Starcevic, K.; Kralj, M.; Ester, K.; Sabol, I.; Grce, M.; Pavelic, K.; Karminski-Zamola, G. Synthesis, antiviral and antitumor activity of 2-substituted-5-amidino-benzimidazoles. Bioorg. Med. Chem., 2007, 15(13), 4419-4426.
[21]
Foks, H.; Pancechowska-Ksepko, D.; Kuzmierkiewicz, W.; Zwolska, Z.; Augustynowicz-Kopec, E.; Janowiec, M. Synthesis and tuberculostatic activity of new benzimidazole derivatives. Chem. Heterocycl. Compd., 2006, 42(5), 611-614.
[22]
Shingalapur, R.V.; Hosamani, K.M.; Keri, R.S. Synthesis and evaluation of in vitro anti-microbial and anti-tubercular activity of 2-styryl benzimidazoles. Eur. J. Med. Chem., 2009, 44(10), 4244-4248.
[23]
Navarrete-Vazquez, G.; Cedillo, R.; Hernandez-Campos, A.; Yepez, L.; Hernandez-Luis, F.; Valdez, J.; Castillo, R. Synthesis and antiparasitic activity of 2-(trifluoromethyl) benzimidazole derivatives. Bioorg. Med. Chem. Lett., 2001, 11(2), 187-190.
[24]
Labanauskas, L.K.; Brukstus, A.B.; Gaidelis, P.G.; Buchinskaite, V.A.; Udrenaite, E.B.; Dauksas, V.K. Synthesis and antiinflammatory activity of some new 1-Acyl derivatives of 2-Methylthio-5, 6-Diethoxybenzimidazole. Pharm. Chem. J., 2000, 34(7), 353-355.
[25]
Peng, X.M.; Cai, G.X.; Zhou, C.H. Recent developments in azole compounds as antibacterial and antifungal agents. Curr. Top. Med. Chem., 2013, 13, 1963-2010.
[26]
Bhattacharya, S.; Chaudhuri, P. Medical implications of benzimidazole derivatives as drugs designed for targeting DNA and DNA associated processes. Curr. Med. Chem., 2008, 15(18), 1762-1777.
[27]
ONiel, M.J.; Smith, M.; Heckelman, P.E. The Merck Index, 13th ed. Merck & Co. Inc., New Jersey, 2001, P-1785, Monograph Number, p. 10074.
[28]
Timmis, G.M.; Epstein, S.S. New antimetabolites of vitamin B12. Nature, 1959, 184, 1383.
[29]
Woolley, D.W. Some biological effects produced by benzimidazole and their reversal by purines. J. Biol. Chem., 1944, 152(2), 225-232.
[30]
Sharma, S.; Gangal, S.; Rauf, A. Convenient one-pot synthesis of novel 2-substituted benzimidazoles, tetrahydrobenzimidazoles and imidazoles and evaluation of their in vitro antibacterial and antifungal activities. Eur. J. Med. Chem., 2009, 44(4), 1751-1757.
[31]
Shingalapur, R.V.; Hosamani, K.M.; Keri, R.S. Synthesis and evaluation of in vitro anti-microbial and anti-tubercular activity of 2-styryl benzimidazoles. Eur. J. Med. Chem., 2009, 44(10), 4244-4248.
[32]
Padalkar, V.S.; Borse, B.N.; Gupta, V.D.; Phatangare, K.R.; Patil, V.S.; Umape, P.G.; Sekar, N. Synthesis and antimicrobial activity of novel 2-substituted benzimidazole, benzoxazole and benzothiazole derivatives. Arab. J. Chem., 2016, 9(Suppl. 2), S1125-S1130.
[33]
Soni, L.K.; Narsinghani, T.; Sethi, A. Anti-microbial benzimidazole derivatives: synthesis and in vitro biological evaluation. Med. Chem. Res., 2012, 21(12), 4330-4334.
[34]
Sathaiah, G.; Kumar, A.R.; Shekhar, A.C.; Raju, K.; Rao, P.S.; Narsaiah, B.; Sridhar, B. Design and synthesis of positional isomers of 1-alkyl-2-trifluoromethyl-5 or 6-substituted benzimidazoles and their antimicrobial activity. Med. Chem. Res., 2013, 22(3), 1229-1237.
[35]
Kumar, T.A.; Babu, P.K.; Devi, B.R. Syntheses of arylcinnamic acids, using Alum-Cs2CO3 as precursors of new 2-heterostyrylbenzimidazoles and their antimicrobial evaluation. Med. Chem. Res., 2015, 24(3), 1351-1364.
[36]
Ulkuseven, B.; Tavman, A.; Otuk, G.; Birteksoz, S. Antimicrobial activity of FeIII, CuII, AgI, ZnII and HgII complexes of 2-(2-hydroxy-5-bromo/nitro-phenyl)-1H-and 2-(2-hydroxyphenyl)-5-methyl/chloro/nitro-1H-benzimidazoles. Folia Microbiol., 2002, 47(5), 481-487.
[37]
Tavman, A.; Birteksoz, S.; Otuk, G. Antimicrobial activity of 1, 2-bis-[2-(5-R)-1H-benzimidazolyl]-1, 2-ethanediols, 1, 4-bis-[2-(5-R)-1H-benzimidazolyl]-1, 2, 3, 4-butanetetraols and their FeIII, CuII, and AgI complexes. Folia Microbiol., 2005, 50(6), 467-472.
[38]
Tavman, A.; Birteksoz, S.; Otuk, G. Antimicrobial activity of ZnII, CdII, and HgII complexes of 1, 2-bis-[2-(5-R)-1H-benzimidazolyl]-1, 2-ethanediols and 1, 4-bis-[2-(5-R)-1H-benzimidazolyl]-1, 2, 3, 4-butanetetraols. Folia Microbiol., 2005, 50(6), 473-478.
[39]
Aghatabay, N.M.; Neshat, A.; Karabiyik, T.; Somer, M.; Haciu, D.; Dulger, B. Synthesis, characterization and antimicrobial activity of Fe (II), Zn (II), Cd (II) and Hg (II) complexes with 2, 6-bis (benzimidazol-2-yl) pyridine ligand. Eur. J. Med. Chem., 2007, 42(2), 205-213.
[40]
Tavman, A.; Ikiz, S.; Bagcigil, A.F.; Ozgur, N.Y.; Ak, S. Spectral characterization and antibacterial effect of 2-methyl-6-(5-H-Me-Cl-NO 2-1H-benzimidazol-2-yl)-phenols and some transition metal complexes. Russ. J. Inorg. Chem., 2010, 55(2), 215-222.
[41]
Janupally, R.; Jeankumar, V.U.; Bobesh, K.A.; Soni, V.; Devi, P.B.; Pulla, V.K.; Sriram, D. Structure-guided design and development of novel benzimidazole class of compounds targeting DNA gyraseB enzyme of Staphylococcus aureus. Bioorg. Med. Chem., 2014, 22(21), 5970-5987.
[42]
Rashedy, A.A.E.; Aboul-Enein, H.Y. Benzimidazole derivatives as potential chemotherapeutic agents. Curr. Drug Ther., 2013, 8(1), 1-14.
[43]
Khalafi-Nezhad, A.; Rad, M.S.; Mohabatkar, H.; Asrari, Z.; Hemmateenejad, B. Design, synthesis, antibacterial and QSAR studies of benzimidazole and imidazole chloroaryloxyalkyl derivatives. Bioorg. Med. Chem., 2005, 13(6), 1931-1938.
[44]
Bennett, G.A.; Mullen, G.B.; Mitchell, J.T.; Jones, W.E.; Allen, S.D.; Kinsolving, C.R.; Georgiev, V.S. Studies on antifungal agents 30. Novel substituted 3-(2-furanyl)-3-(1H-imidazol-1-ylmethyl)-2-methyl-5-phenyl (or phenyloxymethy)-isoxazolidines. Eur. J. Med. Chem., 1989, 24(6), 579-583.
[45]
Guven, O.O.; Erdogan, T.; Goker, H.; Yildiz, S. Synthesis and antimicrobial activity of some novel phenyl and benzimidazole substituted benzyl ethers. Bioorg. Med. Chem. Lett., 2007, 17(8), 2233-2236.
[46]
Patel, R.V.; Patel, P.K.; Kumari, P.; Rajani, D.P.; Chikhalia, K.H. Synthesis of benzimidazolyl-1, 3, 4-oxadiazol-2ylthio-N-phenyl (benzothiazolyl) acetamides as antibacterial, antifungal and antituberculosis agents. Eur. J. Med. Chem., 2012, 53, 41-51.
[47]
Ayhan-Kılcıgil, G.; Altanlar, N. Synthesis and antimicrobial activities of some new benzimidazole derivatives. Il. Farmaco, 2003, 58(12), 1345-1350.
[48]
Iwao, E.; Yamamoto, K.; Yokoyama, Y.; Hirayama, F.; Haga, K. Potent antibacterial activity of Y-754, a novel benzimidazole compound with selective action against Helicobacter pylori. J. Infect. Chemother., 2004, 10(2), 90-96.
[49]
Kumar, R.V.; Gopal, K.R.; Kumar, K.V.S.R.S. Facile synthesis and antimicrobial properties of 2-(substituted-benzylsulfanyl)-1h-benzimidazoles. J. Heterocycl. Chem., 2005, 42(7), 1405-1408.
[50]
Desai, K.G.; Desai, K.R. Green route for the heterocyclization of 2-mercaptobenzimidazole into β-lactum segment derivatives containing–CONH–bridge with benzimidazole: Screening in vitro antimicrobial activity with various microorganisms. Bioorg. Med. Chem., 2006, 14(24), 8271-8279.
[51]
Parikh, K.; Joshi, D. Antibacterial and antifungal screening of newly synthesized benzimidazole-clubbed chalcone derivatives. Med. Chem. Res., 2013, 22(8), 3688-3697.
[52]
Rida, S.M.; El-Hawash, S.A.; Fahmy, H.T.; Hazzaa, A.A.; El-Meligy, M.M. Synthesis of novel benzofuran and related benzimidazole derivatives for evaluation of in vitro anti-HIV-1, anticancer and antimicrobial activities. Arch. Pharm. Res., 2006, 29(10), 826-833.
[53]
Desai, N.C.; Pandya, D.D.; Joshi, V.V.; Rajpara, K.M.; Vaghani, H.V.; Satodiya, H.M. Synthesis, characterization and antimicrobial screening of hybrid molecules containing benzimidazole-pyrazole and pyridine nucleus. Med. Chem. Res., 2012, 21(12), 4463-4472.
[54]
Desai, N.C.; Pandya, D.D.; Kotadiya, G.M.; Desai, P. Synthesis and characterization of novel benzimidazole bearing pyrazoline derivatives as potential antimicrobial agents. Med. Chem. Res., 2014, 23(3), 1474-1487.
[55]
Garudachari, B.; Satyanarayana, M.N.; Thippeswamy, B.; Shivakumar, C.K.; Shivananda, K.N.; Hegde, G.; Isloor, A.M. Synthesis, characterization and antimicrobial studies of some new quinoline incorporated benzimidazole derivatives. Eur. J. Med. Chem., 2012, 54, 900-906.
[56]
Desai, N.C.; Pandya, D.D.; Bhatt, K.A.; Kotadiya, G.M.; Desai, P. Synthesis, antimicrobial, and cytotoxic activities of novel benzimidazole derivatives bearing cyanopyridine and 4-thiazolidinone motifs. Med. Chem. Res., 2014, 23(8), 3823-3835.
[57]
Desai, N.C.; Kotadiya, G.M. Microwave-assisted synthesis of benzimidazole bearing 1, 3, 4-oxadiazole derivatives: screening for their in vitro antimicrobial activity. Med. Chem. Res., 2014, 23(9), 4021-4033.
[58]
Ozkay, Y.; Tunali, Y.; Karaca, H.; Isikdag, I. Antimicrobial activity and a SAR study of some novel benzimidazole derivatives bearing hydrazone moiety. Eur. J. Med. Chem., 2010, 45(8), 3293-3298.
[59]
Ozkay, Y.; Tunalı, Y.; Karaca, H.; Isikdag, I. Antimicrobial activity of a new series of benzimidazole derivatives. Arch. Pharm. Res., 2011, 34(9), 1427-1435.
[60]
Desai, N.C.; Dodiya, A.M.; Shihory, N.R. A search of novel antimicrobial based on benzimidazole and 2-pyridone heterocycles. Med. Chem. Res., 2012, 21(9), 2579-2586.
[61]
Desai, N.C.; Shihory, N.R.; Kotadiya, G.M. Facile synthesis of benzimidazole bearing 2-pyridone derivatives as potential antimicrobial agents. Chin. Chem. Lett., 2014, 25(2), 305-307.
[62]
Desai, N.C.; Shihory, N.R.; Kotadiya, G.M.; Desai, P. Synthesis, antibacterial and antitubercular activities of benzimidazole bearing substituted 2-pyridone motifs. Eur. J. Med. Chem., 2014, 82, 480-489.
[63]
Zhang, H.Z.; Damu, G.L.; Cai, G.X.; Zhou, C.H. Design, synthesis and antimicrobial evaluation of novel benzimidazole type of Fluconazole analogues and their synergistic effects with Chloromycin, Norfloxacin and Fluconazole. Eur. J. Med. Chem., 2013, 64, 329-344.
[64]
Madabhushi, S.; Mallu, K.K.R.; Vangipuram, V.S.; Kurva, S.; Poornachandra, Y.; Kumar, C.G. Synthesis of novel benzimidazole functionalized chiral thioureas and evaluation of their antibacterial and anticancer activities. Bioorg. Med. Chem. Lett., 2014, 24(20), 4822-4825.
[65]
Fahmy, H.H.; El-Masry, A.; Abdelwahed, S.A. Synthesis and preliminary antimicrobial screening of new benzimidazole heterocycles. Arch. Pharm. Res., 2001, 24(1), 27-34.
[66]
El-Masry, A.H.; Fahmy, H.H.; Ali Abdelwahed, S.H. Synthesis and antimicrobial activity of some new benzimidazole derivatives. Molecules, 2000, 5(12), 1429-1438.
[67]
Ansari, K.F.; Lal, C. Synthesis, physicochemical properties and antimicrobial activity of some new benzimidazole derivatives. Eur. J. Med. Chem., 2009, 44(10), 4028-4033.
[68]
Ansari, K.F.; Lal, C. Synthesis and evaluation of some new benzimidazole derivatives as potential antimicrobial agents. Eur. J. Med. Chem., 2009, 44(5), 2294-2299.
[69]
Salahuddin; Shaharyar, M.; Mazumder, A.; Abdullah, M.M. Synthesis, characterization and antimicrobial activity of 1, 3, 4-oxadiazole bearing 1H-benzimidazole derivatives. Arab. J. Chem., 2017, 10(Suppl. 1), S503-S508.
[70]
Ansari, K.F.; Lal, C. Synthesis and biological activity of some heterocyclic compounds containing benzimidazole and beta-lactam moiety. J. Chem. Sci., 2009, 121(6), 1017-1025.
[71]
Noolvi, M.; Agrawal, S.; Patel, H.; Badiger, A.; Gaba, M.; Zambre, A. Synthesis, antimicrobial and cytotoxic activity of novel azetidine-2-one derivatives of 1H-benzimidazole. Arab. J. Chem., 2014, 7(2), 219-226.
[72]
Nofal, Z.M.; Fahmy, H.H.; Mohamed, H.S. Synthesis, antimicrobial and molluscicidal activities of new benzimidazole derivatives. Arch. Pharm. Res., 2002, 25(1), 28-38.
[73]
Nofal, Z.M.; Fahmy, H.H.; Mohamed, H.S. Synthesis and antimicrobial activity of new substituted anilinobenzimidazoles. Arch. Pharm. Res., 2002, 25(3), 250-257.
[74]
Vaidya, S.D.; Kumar, B.V.S.; Kumar, R.V.; Bhise, U.N.; Mashelkar, U.C. Synthesis, anti-bacterial, anti-asthmatic and anti-diabetic activities of novel N-substituted-2-(benzo[d]isoxazol-3-ylmethyl)-1H-benzimidazles. J. Heterocycl. Chem., 2007, 44, 685-691.
[75]
Babu, P.K.; Ramadevi, B.; Poornachandra, Y.; Kumar, C.G. Synthesis, antimicrobial, and anticancer evaluation of novel 2-(3-methylindolyl) benzimidazole derivatives. Med. Chem. Res., 2014, 23(9), 3970-3978.
[76]
Vinodkumar, R.; Vaidya, S.D.; Kumar, B.V.S.; Bhise, U.N.; Bhirud, S.B.; Mashelkar, U.C. Synthesis, anti-bacterial, anti-asthmatic and anti-diabetic activities of novel N-substituted-2-(4-phenylethynyl-phenyl)-1H-benzimidazoles and N-substituted 2 [4-(4, 4-dimethyl-thiochroman-6-yl-ethynyl)-phenyl)-1H-benzimidazoles. Eur. J. Med. Chem., 2008, 43(5), 986-995.
[77]
Gill, C.; Jadhav, G.; Shaikh, M.; Kale, R.; Ghawalkar, A.; Nagargoje, D.; Shiradkar, M. Clubbed [1, 2, 3] triazoles by fluorine benzimidazole: A novel approach to H37Rv inhibitors as a potential treatment for tuberculosis. Bioorg. Med. Chem. Lett., 2008, 18(23), 6244-6247.
[78]
Bandyopadhyay, P.; Sathe, M.; Ponmariappan, S.; Sharma, A.; Sharma, P.; Srivastava, A.K.; Kaushik, M.P. Exploration of in vitro time point quantitative evaluation of newly synthesized benzimidazole and benzothiazole derivatives as potential antibacterial agents. Bioorg. Med. Chem. Lett., 2011, 21(24), 7306-7309.
[79]
Kalalbandi, V.K.A.; Seetharamappa, J.; Katrahalli, U.; Bhat, K.G. Synthesis, crystal studies, anti-tuberculosis and cytotoxic studies of 1-[(2E)-3-phenylprop-2-enoyl]-1H-benzimidazole derivatives. Eur. J. Med. Chem., 2014, 79, 194-202.
[80]
Zhang, H.; Lin, J.; Rasheed, S.; Zhou, C. Design, synthesis, and biological evaluation of novel benzimidazole derivatives and their interaction with calf thymus DNA and synergistic effects with clinical drugs. Sci. China Chem., 2014, 57(6), 807-822.
[81]
Şener, E.; Yalçın, I.; Temiz, O.; Oren, I.; Akın, A.; Uçarturk, N. Synthesis and structure-activity relationships of some 2, 5-disubstituted benzoxazoles and benzimidazoles as antimicrobial agents. Farmaco, 1997, 52, 99-103.
[82]
Zhang, D.; Wang, Z.; Xu, W.; Sun, F.; Tang, L.; Wang, J. Design, synthesis and antibacterial activity of novel actinonin derivatives containing benzimidazole heterocycles. Eur. J. Med. Chem., 2009, 44(5), 2202-2210.
[83]
Klimesova, V.; Koci, J.; Waisser, K.; Kaustova, J. New benzimidazole derivatives as antimycobacterial agents. Il Farmaco, 2002, 57(4), 259-265.
[84]
Klimesova, V.; Koci, J.; Pour, M.; Stachel, J.; Waisser, K.; Kaustova, J. Synthesis and preliminary evaluation of benzimidazole derivatives as antimicrobial agents. Eur. J. Med. Chem., 2002, 37(5), 409-418.
[85]
Kazimierczuk, Z.; Andrzejewska, M.; Kaustova, J.; Klimesova, V. Synthesis and antimycobacterial activity of 2-substituted halogenobenzimidazoles. Eur. J. Med. Chem., 2005, 40(2), 203-208.
[86]
Kaplancikli, Z.A.; Turan-Zitouni, G.; Revial, G.; Guven, K. Synthesis and study of antibacterial and antifungal activities of novel 2-[[(benzoxazole/benzimidazole-2-yl) sulfanyl] acetylamino] thiazoles. Arch. Pharm. Res., 2004, 27(11), 1081-1085.
[87]
Joshi, D.; Parikh, K. Synthesis and evaluation of novel benzimidazole derivatives as antimicrobial agents. Med. Chem. Res., 2014, 23(3), 1290-1299.
[88]
Huigens, R.W.; Reyes, S.; Reed, C.S.; Bunders, C.; Rogers, S.A.; Steinhauer, A.T.; Melander, C. The chemical synthesis and antibiotic activity of a diverse library of 2-aminobenzimidazole small molecules against MRSA and multidrug-resistant A. baumannii. Bioorg. Med. Chem., 2010, 18(2), 663-674.
[89]
Tunçbilek, M.; Goker, H.; Ertan, R.; Eryigit, R.; Kendi, E.; Altanlar, N. Synthesis and antimicrobial activity of some new anilino benzimidazoles. Arch. Der. Pharm., 1997, 330(12), 372-376.
[90]
Zhou, B.; Li, B.; Yi, W.; Bu, X.; Ma, L. Synthesis, antioxidant, and antimicrobial evaluation of some 2-arylbenzimidazole derivatives. Bioorg. Med. Chem. Lett., 2013, 23(13), 3759-3763.
[91]
Desai, N.C.; Dodiya, A.M.; Makwana, A.H. Antimicrobial screening of novel synthesized benzimidazole nucleus containing 4-oxo-thiazolidine derivatives. Med. Chem. Res., 2012, 21(9), 2320-2328.
[92]
Goker, H.; Boykin, D.W.; Yildiz, S. Synthesis and potent antimicrobial activity of some novel 2-phenyl or methyl-4H-1-benzopyran-4-ones carrying amidinobenzimidazoles. Bioorg. Med. Chem., 2005, 13(5), 1707-1714.
[93]
Mungra, D.C.; Patel, M.P.; Patel, R.G. Microwave-assisted synthesis of some new tetrazolo [1, 5-a] quinoline-based benzimidazoles catalyzed by p-TsOH and investigation of their antimicrobial activity. Med. Chem. Res., 2011, 20(6), 782-789.
[94]
Bishop, B.C.; Chelton, E.T.J.; Jones, A.S. The antibacterial activity of some fluorine-containing benzimidazoles. Biochem. Pharmacol., 1964, 13(5), 751-754.
[95]
Goker, H.; Tunçbilek, M.; Ayhan, G.; Altanlar, N. Synthesis of some new benzimidazolecarboxamides and evaluation of their antimicrobial activity. Il Farmaco, 1998, 53(6), 415-420.
[96]
Ayhan-Kilcigil, G.; Tunçbilek, M.; Altanlar, N.; Goker, H. Synthesis and antimicrobial activity of some new benzimidazole carboxylates and carboxamides. Il Farmaco, 1999, 54(8), 562-565.
[97]
Goker, H.; Tunçbilek, M.; Suzen, S.; Kus, C.; Altanlar, N. Synthesis and antimicrobial activity of some new 2-Phenyl-N-substituted carboxamido-1H-benzimidazole derivatives. Arch. Der. Pharm., 2001, 334(5), 148-152.
[98]
Ozden, S.; Atabey, D.; Yildiz, S.; Goker, H. Synthesis and potent antimicrobial activity of some novel methyl or ethyl 1H-benzimidazole-5-carboxylates derivatives carrying amide or amidine groups. Bioorg. Med. Chem., 2005, 13(5), 1587-1597.
[99]
Goker, H.; Ozden, S.; Yildiz, S.; Boykin, D.W. Synthesis and potent antibacterial activity against MRSA of some novel 1, 2-disubstituted-1H-benzimidazole-N-alkylated-5-carboxamidines. Eur. J. Med. Chem., 2005, 40(10), 1062-1069.
[100]
Goker, H.; Alp, M.; Yildiz, S. Synthesis and potent antimicrobial activity of some novel N-(alkyl)-2-phenyl-1H-benzimidazole-5-carboxamidines. Molecules, 2005, 10(11), 1377-1386.
[101]
Dhakad, A.; Sharma, M.C.; Chaturvedi, S.C.; Sharma, S. 3DQSAR studies, biological evaluation studies on some substituted 3-chloro-1-[5-(5-chloro-2-phenyl-benzimidazole-1-ylmethyl)-[1, 3, 4] thiadiazole-2-yl]-azetidin-2-one as potential antimicrobial activity. Dig. J. Nanomater. Biostruct., 2009, 4(2), 275-279.
[102]
Ranjith, P.K.; Rajeesh, P.; Haridas, K.R.; Susanta, N.K.; Row, T.N.G.; Rishikesan, R.; Kumari, N.S. Design and synthesis of positional isomers of 5 and 6-bromo-1-[(phenyl) sulfonyl]-2-[(4-nitrophenoxy) methyl]-1H-benzimidazoles as possible antimicrobial and antitubercular agents. Bioorg. Med. Chem. Lett., 2013, 23(18), 5228-5234.
[103]
Kuçukbay, H.; Durmaz, R.; Orhan, E.; Gunal, S. Synthesis, antibacterial and antifungal activities of electron-rich olefins derived benzimidazole compounds. Il Farmaco, 2003, 58(6), 431-437.
[104]
Braun, S.; Botzki, A.; Salmen, S.; Textor, C.; Bernhardt, G.; Dove, S.; Buschauer, A. Design of benzimidazole-and benzoxazole-2-thione derivatives as inhibitors of bacterial hyaluronan lyase. Eur. J. Med. Chem., 2011, 46(9), 4419-4429.
[105]
Tuncbilek, M.; Kiper, T.; Altanlar, N. Synthesis and in vitro antimicrobial activity of some novel substituted benzimidazole derivatives having potent activity against MRSA. Eur. J. Med. Chem., 2009, 44(3), 1024-1033.
[106]
Kus, C.; Sozudonmez, F.; Altanlar, N. Synthesis and antimicrobial activity of some novel 2-[4-(substituted piperazin-/piperidin-1-ylcarbonyl) phenyl]-1H-benzimidazole derivatives. Arch. Pharm. Chem. Life Sci., 2009, 342, 54-60.
[107]
He, Y.; Yang, J.; Wu, B.; Risen, L.; Swayze, E.E. Synthesis and biological evaluations of novel benzimidazoles as potential antibacterial agents. Bioorg. Med. Chem. Lett., 2004, 14(5), 1217-1220.
[108]
Ozden, S.; Karataş, H.; Yildiz, S.; Goeker, H. Synthesis and potent antimicrobial activity of some novel 4-(5, 6-Dichloro-1H-benzimidazol-2-yl)-N-substituted benzamides. Arch. Der. Pharm., 2004, 337(10), 556-562.
[109]
Kucukbay, H.; Durmaz, R.; Okyucu, N.; Gunal, S. Antifungal activity of some bis-5-methylbenzimidazole compounds. Folia Microbiol., 2003, 48(5), 679-681.
[110]
Bassyouni, F.A.; Saleh, T.S. EL-Hefnawi, M.M.; EL-Moez, S.I.A.; EL-Senousy, W.M.; Abdel-Rehim, M.E. Synthesis, pharmacological activity evaluation and molecular modeling of new polynuclear heterocyclic compounds containing benzimidazole derivatives. Arch. Pharm. Res., 2012, 35(12), 2063-2075.
[111]
Hu, L.; Kully, M.L.; Boykin, D.W.; Abood, N. Synthesis and in vitro activity of dicationic bisbenzimidazoles as a new class of anti-MRSA and anti-VRE agents. Bioorg. Med. Chem. Lett., 2009, 19(5), 1292-1295.
[112]
Hu, L.; Kully, M.L.; Boykin, D.W.; Abood, N. Optimization of the central linker of dicationic bis-benzimidazole anti-MRSA and anti-VRE agents. Bioorg. Med. Chem. Lett., 2009, 19(13), 3374-3377.
[113]
Padalkar, V.S.; Gupta, V.D.; Phatangare, K.R.; Patil, V.S.; Umape, P.G.; Sekar, N. Synthesis of novel dipole-benzimidazole, benzoxazole and benzthiazole from cyanuric chloride: Structural, photophysical and antimicrobial studies. J. Saudi Chem. Soc., 2014, 18, 262-268.
[114]
Zhang, S.L.; Damu, G.L.; Zhang, L.; Geng, R.X.; Zhou, C.H. Synthesis and biological evaluation of novel benzimidazole derivatives and their binding behavior with bovine serum albumin. Eur. J. Med. Chem., 2012, 55, 164-175.
[115]
Seenaiah, D.; Reddy, P.R.; Reddy, G.M.; Padmaja, A.; Padmavathi, V. Synthesis, antimicrobial and cytotoxic activities of pyrimidinyl benzoxazole, benzothiazole and benzimidazole. Eur. J. Med. Chem., 2014, 77, 1-7.
[116]
Moreira, J.B.; Mann, J.; Neidle, S.; McHugh, T.D.; Taylor, P.W. Antibacterial activity of head-to-head bis-benzimidazoles. Int. J. Antimicrob. Agents, 2013, 42(4), 361-366.
[117]
Rohini, R.; Shanker, K.; Reddy, P.M.; Ho, Y.P.; Ravinder, V. Mono and bis-6-arylbenzimidazo[1, 2-c[quinazolines: A new class of antimicrobial agents. Eur. J. Med. Chem., 2009, 44(8), 3330-3339.
[118]
Mohamed, B.G.; Hussein, M.A.; Abdel-Alim, A.A.M.; Hashem, M. Synthesis and antimicrobial activity of some new 1-alkyl-2-alkylthio-1, 2, 4-triazolobenzimidazole derivatives. Arch. Pharm. Res., 2006, 29(1), 26-33.
[119]
Sangani, C.B.; Jardosh, H.H.; Patel, M.P.; Patel, R.G. Microwave-assisted synthesis of pyrido [1, 2-a] benzimidazole derivatives of β-aryloxyquinoline and their antimicrobial and antituberculosis activities. Med. Chem. Res., 2013, 22(6), 3035-3047.
[120]
Jardosh, H.H.; Sangani, C.B.; Patel, M.P.; Patel, R.G. One step synthesis of pyrido[1, 2-a]benzimidazole derivatives of aryloxypyrazole and their antimicrobial evaluation. Chin. Chem. Lett., 2013, 24(2), 123-126.
[121]
Bharti, N.; Garza, M.G.; Cruz-Vega, D.E.; Castro-Garza, J.; Saleem, K.; Naqvi, F.; Azam, A. Synthesis, characterization and antiamoebic activity of benzimidazole derivatives and their vanadium and molybdenum complexes. Bioorg. Med. Chem. Lett., 2002, 12(6), 869-871.
[122]
Ozden, S.; Atabey, D.; Yıldız, S.; Goker, H. Synthesis and potent antimicrobial activity of some novel methyl or ethyl 1H-benzimidazole-5-carboxylates derivatives carrying amide or amidine groups. Bioorg. Med. Chem., 2005, 13(5), 1587-1597.
[123]
Kathrotiya, H.G.; Patel, M.P. An efficient synthesis of 3′-indolyl substituted pyrido [1,2-a] benzimidazoles as potential antimicrobial and antioxidant agents. J. Chem. Sci., 2013, 125(5), 993-1001.
[124]
Navarrete-Vazquez, G.; Cedillo, R.; Hernandez-Campos, A.; Yepez, J.; Hernndez-Luis, F.; Valldez, J.; Morales, R.; Cortes, R.; Hernandez, M.; Castillo, R. Bioorg. Med. Chem. Lett., 2001, 11, 187-190.
[125]
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(5), 232-243.
[126]
Bahri, U.; Aydin, T.; Gulten, O. Synthesis, Characterization and Antimicrobial Activity of d 8-10 Metal Complexes of some 2-Substituted-1H-Benzimidazoles. Met. Based Drugs, 1900, 6(3), 163-167.
[127]
Gunal, S.; Kaloglu, N.; Ozdemir, I.; Demir, S.; Ozdemir, I. Novel benzimidazolium salts and their silver complexes: Synthesis and antibacterial properties. Inorg. Chem. Commun., 2012, 21, 142-146.
[128]
Gumuş, F.; Pamuk, I.; Ozden, T.; Yıldız, S.; Diril, N.; Oksuzoglu, E.; Ozkul, A. Synthesis, characterization and in vitro cytotoxic, mutagenic and antimicrobial activity of platinum (II) complexes with substituted benzimidazole ligands. J. Inorg. Biochem., 2003, 94(3), 255-262.
[129]
Arjmand, F.; Mohani, B.; Ahmad, S. Synthesis, antibacterial, antifungal activity and interaction of CT-DNA with a new benzimidazole derived Cu (II) complex. Eur. J. Med. Chem., 2005, 40(11), 1103-1110.
[130]
Arjmand, F.; Parveen, S.; Afzal, M.; Shahid, M. Synthesis, characterization, biological studies (DNA binding, cleavage, antibacterial and topoisomerase I) and molecular docking of copper (II) benzimidazole complexes. J. Photochem. Photobiol. B Bio, 2012, 114, 15-26.
[131]
Siddiqi, Z.A.; Shahid, A.M.; Khalid, M.; Sharma, P.K.; Siddique, A. Spectroscopic, luminescence, electrochemical and antimicrobial studies of lanthanide complexes of bis-benzimidazole derived ligands. J. Mol. St., 2013, 1037, 402-411.
[132]
Kalinowska-Lis, U.; Felczak, A.; Chęcinska, L.; Lisowska, K.; Ochocki, J. Synthesis, characterization and antimicrobial activity of silver (I) complexes of hydroxymethyl derivatives of pyridine and benzimidazole. J. Organomet. Chem., 2014, 749, 394-399.

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