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Mini-Reviews in Medicinal Chemistry

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

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Review Article

Benzimidazole: A Milestone in the Field of Medicinal Chemistry

Author(s): Mahesh S. Vasava, Manoj N. Bhoi, Sanjay K. Rathwa, Divya J. Jethava, Prachi T. Acharya, Dhaval B. Patel and Hitesh D. Patel*

Volume 20, Issue 7, 2020

Page: [532 - 565] Pages: 34

DOI: 10.2174/1389557519666191122125453

Price: $65

Abstract

In the last 2-3 decades, the broad research in the application of benzimidazole derivatives made it important for mankind. Many scientists have worked on benzimidazole derivatives and they found that this compound has a diverse role in the field of medicinal chemistry. Few benzimidazole derivatives are currently in the market as a drug candidate against various diseases. Moreover, the benzimidazole derivatives exhibit pharmacological activities such as anti-tuberculosis, anti-malarial, antihistamine, antimicrobial, antiviral, antidiabetic, anticancer, anti-fungal, anti-inflammatory, analgesic, anti-HIV, etc. In this review, we have summarized various derivatives of benzimidazole which have been prepared by many researchers to understand the chemistry as well as diverse pharmacological activities. These findings may lead the scientists who are working in the field of medicinal chemistry to the development of benzimidazole based drug candidates in the future.

Keywords: Benzimidazole, biological activity, anti-tuberculosis activity, anti-HIV activity, anti-malarial activity, antidiabetic.

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[1]
Gupta, R.R.; Kumar, M.; Gupta, V. Heterocyclic Chemistry: Volume II; Five-Membered Heterocycles. Springer Science & Business Media.. , 2013.
[2]
Mohammad, A. A mini review: Biological significances of nitrogen hetero atom containing heterocyclic compounds. Int. J. Bioorg. Chem., 2017, 2, 146-152.
[3]
Chen, Z.Z.; Li, S.Q.; Liao, W.L.; Xie, Z.G.; Wang, M.S.; Cao, Y.; Zhang, J.; Xu, Z.G. Efficient method for the synthesis of fused benzimidazole-imidazoles via deprotection and cyclization reactions. Tetrahedron, 2015, 71(44), 8424-8427.
[4]
Wright, J.B. The chemistry of the benzimidazoles. Chem. Rev., 1951, 48(3), 397-541.
[PMID: 24541208]
[5]
Arrang, J.M.; Garbarg, M.; Lancelot, J.C.; Lecomte, J.M.; Pollard, H.; Robba, M.; Schunack, W.; Schwartz, J.C. Highly potent and selective ligands for a new class H3 of histamine receptor. Invest. Radiol., 1988, 23(Suppl. 1), S130-S132.
[PMID: 2848779]
[6]
Sugumaran, M.; Kumar, M.Y. Synthesis and biological activity of novel 2, 5-disubstituted benzimidazole derivatives. Int. J. Pharm. Sci. Drug Res., 2012, 4(1), 80-83.
[7]
Horton, D.A.; Bourne, G.T.; Smythe, M.L. The combinatorial synthesis of bicyclic privileged structures or privileged substructures. Chem. Rev., 2003, 103(3), 893-930.
[PMID: 12630855]
[8]
Rathee, P.S.; Dhankar, R.; Bhardwaj, S.; Gupta, M.; Kumar, R. Synthesis and antimicrobial studies of substituted 2-phenylbenzimidazole derivatives. J. Appl. Pharm. Sci., 2011, 1(10), 14.
[9]
Nakano, H.; Inoue, T.; Kawasaki, N.; Miyataka, H.; Matsumoto, H.; Taguchi, T.; Inagaki, N.; Nagai, H.; Satoh, T. Synthesis of benzimidazole derivatives as antiallergic agents with 5-lipoxygenase inhibiting action. Chem. Pharm. Bull. (Tokyo), 1999, 47(11), 1573-1578.
[PMID: 10605056]
[10]
Fonseca, T.; Gigante, B.; Gilchrist, T.L. A short synthesis of phenanthro [2, 3-d] imidazoles from dehydroabietic acid. Application of the methodology as a convenient route to benzimidazoles. Tetrahedron, 2001, 57(9), 1793-1799.
[11]
Serafin, B.; Borkowska, G.; Główczyk, J.; Kowalska, I.; Rump, S. Potential antihypertensive benzimidazole derivatives. Pol. J. Pharmacol. Pharm., 1989, 41(1), 89-96.
[PMID: 2587441]
[12]
Bethke, T.; Brunkhorst, D.; von der Leyen, H.; Meyer, W.; Nigbur, R.; Scholz, H. Mechanism of action and cardiotonic activity of a new phosphodiesterase inhibitor, the benzimidazole derivative adibendan (BM 14.478), in guinea-pig hearts. Naunyn Schmiedebergs Arch. Pharmacol., 1988, 337(5), 576-582.
[PMID: 2457816]
[13]
Khan, F.R.; Asnani, A.J. Synthesis and antiulcer, anti-secretory activity of some new substituted 2-(pyrimidinylsulfinyl) benzamidazoles derivatives. Int. J. Pharm. Biomed., 2011, 2(2), 695-700.
[14]
Al-Douh, M.H.; Sahib, H.B.; Osman, H.; Abd Hamid, S.; Salhimi, S.M. Anti-proliferation effects of benzimidazole derivatives on HCT-116 colon cancer and MCF-7 breast cancer cell lines. Asian Pac. J. Cancer Prev., 2012, 13(8), 4075-4079.
[PMID: 23098519]
[15]
Lazer, E.S.; Matteo, M.R.; Possanza, G.J. Benzimidazole derivatives with atypical antiinflammatory activity. J. Med. Chem., 1987, 30(4), 726-729.
[PMID: 3104589]
[16]
Aydin, S.; Beis, R.; Can, Ö.D. Analgesic and antispasmodic activities of 2-(2-nitro-phenyl)-1H-benzimidazole 5-carboxylic acid: Evidence for the importance of the 2-(o-substituted phenyl) group. Pharmazie, 2003, 58(6), 405-408.
[PMID: 12857004]
[17]
Ateş-Alagöz, Z.; Kuş, C.; Coban, 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.
[PMID: 16206826]
[18]
Kazimierczuk, Z.; Upcroft, J.A.; Upcroft, P.; Górska, A.; Starościak, B.; Laudy, A. Synthesis, antiprotozoal and antibacterial activity of nitro- and halogeno-substituted benzimidazole derivatives. Acta Biochim. Pol., 2002, 49(1), 185-195.
[PMID: 12136939]
[19]
Vinodkumar, R.; Vaidya, S.D.; Siva Kumar, B.V.; 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.
[PMID: 17825955]
[20]
Pashinskiĭ, V.G.; Romanova, T.V.; Mukhina, N.A.; Shkrabova, L.V.; Tetenchuk, K.P. Diuretic activity of benzimidazole urea derivatives. Farmakologiiai toksikologiia., 1978, 41(2), 196-199.
[21]
Ng, R.A.; Guan, J.; Alford, V.C., Jr; Lanter, J.C.; Allan, G.F.; Sbriscia, T.; Linton, O.; Lundeen, S.G.; Sui, Z. Synthesis and SAR of potent and selective androgen receptor antagonists: 5,6-Dichloro-benzimidazole derivatives. Bioorg. Med. Chem. Lett., 2007, 17(3), 784-788.
[PMID: 17095226]
[22]
Oya, U.; Ayla, B.; Cenk, A.; Berna, T.M.; Zafer, G. Synthesis and evaluation of the anticonvulsant activities of some 5-(4-substitutedbenzylidene)-6-methyl-4, 5-dihydropyridazine-3(2H)-ones. Fabad. J. Pharm. Sci., 2004, 29, 185-194.
[23]
Thakurdesai, P.A.; Wadodkar, S.G.; Chopade, C.T. Synthesis and anti-inflammatory activity of some benzimidazole-2-carboxylic acids. Pharmacologyonline, 2007, 1, 314-329.
[24]
Galal, S.A.; Hegab, K.H.; Kassab, A.S.; Rodriguez, M.L.; Kerwin, S.M.; el-Khamry, A.M.; el-Diwani, H.I. New transition metal ion complexes with benzimidazole-5-carboxylic acid hydrazides with antitumor activity. Eur. J. Med. Chem., 2009, 44(4), 1500-1508.
[PMID: 18752870]
[25]
Mederski, W.W.; Dorsch, D.; Anzali, S.; Gleitz, J.; Cezanne, B.; Tsaklakidis, C. Halothiophene benzimidazoles as P1 surrogates of inhibitors of blood coagulation factor Xa. Bioorg. Med. Chem. Lett., 2004, 14(14), 3763-3769.
[PMID: 15203158]
[26]
Rathod, C.P.; Rajurkar, R.M.; Thonte, S.S. Benzimidazole synthesis and biological evaluation: A review. Indo Am. J. Pharm. Res., 2013, 2323-2329.
[27]
Wright, J.B. The chemistry of the benzimidazoles. Chem. Rev., 1951, 48(3), 397-541.
[PMID: 24541208]
[28]
Bhatnagar, A.; Sharma, P.K.; Kumar, N. A review on “Imidazole’s”: Their chemistry and pharmacological potentials. Int. J. Pharm. Tech. Res., 2011, 3, 268-282.
[29]
Ingle, R.G.; Magar, D.D. Heterocyclic chemistry of benzimidazoles and potential activities of derivatives. Int. J. Drug. Res. Tech., 2011, 1, 26-32.
[30]
Gaba, M.; Singh, D.; Singh, S.; Sharma, V.; Gaba, P. Synthesis and pharmacological evaluation of novel 5-substituted-1-(phenylsulfonyl)-2-methylbenzimidazole derivatives as anti-inflammatory and analgesic agents. Eur. J. Med. Chem., 2010, 45(6), 2245-2249.
[PMID: 20172630]
[31]
Ingle, R.G.; Magar, D.D. Heterocyclic chemistry of benzimidazoles and potential activities of derivatives. Int. J. Pharm. Tech. Res., 2017, 1(1), 7.
[32]
Hanan, E.J.; Chan, B.K.; Estrada, A.A.; Shore, D.G.; Lyssikatos, J.P. Mild and general one-pot reduction and cyclization of aromatic and heteroaromatic 2-nitroamines to bicyclic 2h-imidazoles. Synlett, 2010, 18, 2759-2764.
[33]
Bahrami, K.; Khodaei, M.M.; Kavianinia, I. A simple and efficient one-pot synthesis of 2-substituted benzimidazoles. Synthesis, 2007, 04, 547-550.
[34]
Klaehn, J.R.; Peterson, E.S.; Wertsching, A.K.; Orme, C.J.; Luther, T.A.; Jones, M.G. inventors Battelle Energy Alliance LLC, assignee. Polymeric media comprising polybenzimidazoles N-substituted with organic-inorganic hybrid moiety. United States patent US 7,632,898 , 2009.
[35]
Wray, B.C.; Stambuli, J.P. Synthesis of N-arylindazoles and benzimidazoles from a common intermediate. Org. Lett., 2010, 12(20), 4576-4579.
[PMID: 20849145]
[36]
Caron, S.; Jones, B.P.; Wei, L. Preparation of substituted benzimidazoles and imidazopyridines using 2, 2, 2-trichloroethyl imidates. Synthesis, 2012, 44(19), 3049-3054.
[37]
Peng, J.; Ye, M.; Zong, C.; Hu, F.; Feng, L.; Wang, X.; Wang, Y.; Chen, C. Copper-catalyzed intramolecular C-N bond formation: A straightforward synthesis of benzimidazole derivatives in water. J. Org. Chem., 2011, 76(2), 716-719.
[PMID: 21175149]
[38]
Saha, D.; Saha, A.; Ranu, B.C. Remarkable influence of substituent in ionic liquid in control of reaction: Simple, efficient and hazardous organic solvent free procedure for the synthesis of 2-aryl benzimidazoles promoted by ionic liquid,[pmim] BF 4. Green Chem., 2009, 11(5), 733-737.
[39]
Diao, X.; Wang, Y.; Jiang, Y.; Ma, D. Assembly of substituted 1H-benzimidazoles and 1,3-dihydrobenzimidazol-2-ones via CuI/L-proline catalyzed coupling of aqueous ammonia with 2-iodoacetanilides and 2-iodophenylcarbamates. J. Org. Chem., 2009, 74(20), 7974-7977.
[PMID: 19775088]
[40]
Venkatesh, C.; Sundaram, G.S.; Ila, H.; Junjappa, H. Palladium-catalyzed intramolecular N-arylation of heteroarenes: A novel and efficient route to benzimidazo[1,2-a]quinolines. J. Org. Chem., 2006, 71(3), 1280-1283.
[PMID: 16438556]
[41]
Devine, W.; Thomas, S.M.; Erath, J.; Bachovchin, K.A.; Lee, P.J.; Leed, S.E.; Rodriguez, A.; Sciotti, R.J.; Mensa-Wilmot, K.; Pollastri, M.P. Antiparasitic Lead Discovery: Toward optimization of a chemotype with activity against multiple protozoan parasites. ACS Med. Chem. Lett., 2017, 8(3), 350-354.
[PMID: 28337329]
[42]
Alp, M.; Göker, H.; Brun, R.; Yildiz, S. Synthesis and antiparasitic and antifungal evaluation of 2′-arylsubstituted-1H,1‘H-[2,5’]bisbenzimidazolyl-5-carboxamidines. Eur. J. Med. Chem., 2009, 44(5), 2002-2008.
[PMID: 19010569]
[43]
Valdez, J.; Cedillo, R.; Hernández-Campos, A.; Yépez, L.; Hernández-Luis, F.; Navarrete-Vázquez, G.; Tapia, A.; Cortés, R.; Hernández, M.; Castillo, R. Synthesis and antiparasitic activity of 1H-benzimidazole derivatives. Bioorg. Med. Chem. Lett., 2002, 12(16), 2221-2224.
[PMID: 12127542]
[44]
Rojas-Aguirre, Y.; Castillo, I.; Hernández, D.J.; Nogueda-Torres, B.; Márquez-Navarro, A.; Villalobos, J.C.; Sánchez-Bartéz, F.; Sánchez-Torres, L.; Gracia-Mora, I.; Castillo, R.; Hernández-Luis, F. Diversity in the supramolecular interactions of 5, 6-dichloro-2-(trifluoromethyl)-1H-benzimidazole with modified cyclodextrins: Implications for physicochemical properties and antiparasitic activity. Carbohydr. Polym., 2012, 87(1), 471-479.
[45]
Farahat, A.A.; Ismail, M.A.; Kumar, A.; Wenzler, T.; Brun, R.; Paul, A.; Wilson, W.D.; Boykin, D.W. Indole and benzimidazole bichalcophenes: Synthesis, DNA binding and antiparasitic activity. Eur. J. Med. Chem., 2018, 143, 1590-1596.
[PMID: 29126729]
[46]
Robbins, N.; Caplan, T.; Cowen, L.E. Molecular evolution of antifungal drug resistance. Annu. Rev. Microbl., 2017, 8(71), 753-775.
[47]
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, S1125-S1130.
[48]
Ramprasad, J.; Nayak, N.; Dalimba, U.; Yogeeswari, P.; Sriram, D.; Peethambar, S.K.; Achur, R.; Kumar, H.S. Synthesis and biological evaluation of new imidazo[2,1-b][1,3,4]thiadiazole-benzimidazole derivatives. Eur. J. Med. Chem., 2015, 95, 49-63.
[PMID: 25794789]
[49]
Liu, H.B.; Gao, W.W.; Tangadanchu, V.K.R.; Zhou, C.H.; Geng, R.X. Novel aminopyrimidinyl benzimidazoles as potentially antimicrobial agents: Design, synthesis and biological evaluation. Eur. J. Med. Chem., 2018, 143, 66-84.
[PMID: 29172083]
[50]
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.
[PMID: 19540630]
[51]
Fang, X.J.; Jeyakkumar, P.; Avula, S.R.; Zhou, Q.; Zhou, C.H. 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.
[PMID: 27117429]
[52]
Arika, W.M.; Abdirahman, Y.A.; Mawia, M.A.; Wambua, K.F.; Nyamai, D.M.; Ogola, P.E.; Kiboi, N.G.; Nyandoro, H.O.; Agyirifo, D.S.; Ngugi, M.P.; Njagi, E.N. In vivo antidiabetic activity of the aqueous leaf extract of Croton macrostachyus in alloxan induced diabetic mice. Pharm. Anal. Acta, 2015, 6, 447.
[53]
IDF Diabetes Atlas, 5th edition annual update,.. 2012.www.indiaenvironmentportal.org.in/files/file/diabetes%20atlas%202012.pdf
[54]
Dinparast, L.; Valizadeh, H.; Bahadori, M.B.; Soltani, S.; Asghari, B.; Rashidi, M.R. Design, synthesis, α-glucosidase inhibitory activity, molecular docking and QSAR studies of benzimidazole derivatives. J. Mol. Struct., 2016, 1114, 84-94.
[55]
Kwak, H.J.; Pyun, Y.M.; Kim, J.Y.; Pagire, H.S.; Kim, K.Y.; Kim, K.R.; Rhee, S.D.; Jung, W.H.; Song, J.S.; Bae, M.A.; Lee, D.H.; Ahn, J.H. Synthesis and biological evaluation of aminobenzimidazole derivatives with a phenylcyclohexyl acetic acid group as anti-obesity and anti-diabetic agents. Bioorg. Med. Chem. Lett., 2013, 23(16), 4713-4718.
[PMID: 23810496]
[56]
Patil, V.S.; Nandre, K.P.; Ghosh, S.; Rao, V.J.; Chopade, B.A.; Sridhar, B.; Bhosale, S.V.; Bhosale, S.V. Synthesis, crystal structure and antidiabetic activity of substituted (E)-3-(Benzo [d]thiazol-2-ylamino) phenylprop-2-en-1-one. Eur. J. Med. Chem., 2013, 59, 304-309.
[PMID: 23262035]
[57]
Vinodkumar, R.; Vaidya, S.D.; Siva Kumar, B.V.; 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.
[PMID: 17825955]
[58]
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.
[PMID: 20122763]
[59]
Minami, M.; Toya, T.; Katao, Y.; Maekawa, K.; Nakamura, S.; Onogi, T.; Kaneko, S.; Satoh, M. Cloning and expression of a cDNA for the rat kappa-opioid receptor. FEBS Lett., 1993, 329(3), 291-295.
[PMID: 8103466]
[60]
Kankala, S.; Kankala, R.K.; Gundepaka, P.; Thota, N.; Nerella, S.; Gangula, M.R.; Guguloth, H.; Kagga, M.; Vadde, R.; Vasam, C.S. Regioselective synthesis of isoxazole-mercaptobenzimidazole hybrids and their in vivo analgesic and anti-inflammatory activity studies. Bioorg. Med. Chem. Lett., 2013, 23(5), 1306-1309.
[PMID: 23357631]
[61]
Gaba, M.; Gaba, P.; Uppal, D.; Dhingra, N.; Bahia, M.S.; Silakari, O.; Mohan, C. Benzimidazole derivatives: Search for GI-friendly anti-inflammatory analgesic agents. Acta Pharm. Sin. B, 2015, 5(4), 337-342.
[PMID: 26579464]
[62]
Chhajed, S.S.; Upasani, C.D. Synthesis and in-silico molecular docking simulation of 3-chloro-4-substituted-1-(2-(1H-benzimidazol-2-yl) phenyl))-azetidin-2-ones as novel analgesic anti-inflammatory agent. Arab. J. Chem., 2016, 9, S1779-S1785.
[63]
Mariappan, G.; Hazarika, R.; Alam, F.; Karki, R.; Patangia, U.; Nath, S. Synthesis and biological evaluation of 2-substituted benzimidazole derivatives. Arab. J. Chem., 2015, 8(5), 715-719.
[64]
Achar, K.C.; Hosamani, K.M.; Seetharamareddy, H.R. In-vivo analgesic and anti-inflammatory activities of newly synthesized benzimidazole derivatives. Eur. J. Med. Chem., 2010, 45(5), 2048-2054.
[PMID: 20133024]
[65]
De Martino, J.K.; Boger, D.L. Glycinamide ribonucleotide transformylase (GAR TFase) as a target for cancer therapy. Drugs Future, 2008, 33, 969-979.
[66]
Curran, W.J. New chemotherapeutic agents: Update of major chemoradiation trials in solid tumors. Oncology, 2002, 63(Suppl. 2), 29-38.
[PMID: 12466642]
[67]
Cheng, J.; Xie, J.; Luo, X. Synthesis and antiviral activity against Coxsackie virus B3 of some novel benzimidazole derivatives. Bioorg. Med. Chem. Lett., 2005, 15(2), 267-269.
[PMID: 15603937]
[68]
Tonelli, M.; Novelli, F.; Tasso, B.; Vazzana, I.; Sparatore, A.; Boido, V.; Sparatore, F.; La Colla, P.; Sanna, G.; Giliberti, G.; Busonera, B.; Farci, P.; Ibba, C.; Loddo, R. Antiviral activity of benzimidazole derivatives. III. Novel anti-CVB-5, anti-RSV and anti-Sb-1 agents. Bioorg. Med. Chem., 2014, 22(17), 4893-4909.
[PMID: 25082514]
[69]
Porcari, A.R.; Devivar, R.V.; Kucera, L.S.; Drach, J.C.; Townsend, L.B. Design, synthesis, and antiviral evaluations of 1-(substituted benzyl)-2-substituted-5,6-dichlorobenzimidazoles as nonnucleoside analogues of 2,5,6-trichloro-1-(β-D-ribofuranosyl)benzimidazole. J. Med. Chem., 1998, 41(8), 1252-1262.
[PMID: 9548815]
[70]
Husain, A.; Rashid, M.; Shaharyar, M.; Siddiqui, A.A.; Mishra, R. Benzimidazole clubbed with triazolo-thiadiazoles and triazolo-thiadiazines: New anticancer agents. Eur. J. Med. Chem., 2013, 62, 785-798.
[PMID: 23333063]
[71]
Sharma, A.; Luxami, V.; Paul, K. Synthesis, single crystal and antitumor activities of benzimidazole-quinazoline hybrids. Bioorg. Med. Chem. Lett., 2013, 23(11), 3288-3294.
[PMID: 23611732]
[72]
Paul, K.; Sharma, A.; Luxami, V. Synthesis and in vitro antitumor evaluation of primary amine substituted quinazoline linked benzimidazole. Bioorg. Med. Chem. Lett., 2014, 24(2), 624-629.
[PMID: 24360999]
[73]
El-Gohary, N.S.; Shaaban, M.I. Synthesis and biological evaluation of a new series of benzimidazole derivatives as antimicrobial, antiquorum-sensing and antitumor agents. Eur. J. Med. Chem., 2017, 131, 255-262.
[PMID: 28334654]
[74]
Olbe, L.; Carlsson, E.; Lindberg, P. A proton-pump inhibitor expedition: The case histories of omeprazole and esomeprazole. Nat. Rev. Drug Discov., 2003, 2(2), 132-139.
[PMID: 12563304]
[75]
Sachs, G.; Wallmark, B. The gastric H+, K+-ATPase: The site of action of omeprazole. Scand. J. Gastroenterol., 1989, 24(Suppl. 166), 3-11.
[76]
Sharma, R.; Bali, A.; Chaudhari, B.B. Synthesis of methanesulphonamido-benzimidazole derivatives as gastro-sparing antiinflammatory agents with antioxidant effect. Bioorg. Med. Chem. Lett., 2017, 27(13), 3007-3013.
[PMID: 28512025]
[77]
Kubo, K.; Oda, K.; Kaneko, T.; Satoh, H.; Nohara, A. Synthesis of 2-[[(4-fluoroalkoxy-2-pyridyl)methyl]sulfinyl]-1H- benzimidazoles as antiulcer agents. Chem. Pharm. Bull. (Tokyo), 1990, 38(10), 2853-2858.
[PMID: 2076571]
[78]
Cereda, E.; Turconi, M.; Ezhaya, A.; Bellora, E.; Brambilla, A.; Pagani, F.; Donetti, A. Anti-secretory and anti-ulcer activities of some new 2-(2-pyridylmethyl-sulfinyl)-benzimidazoles. Eur. J. Med. Chem., 1987, 22(6), 527-537.
[79]
Hough, L.B. Genomics meets histamine receptors: New subtypes, new receptors. Mol. Pharmacol., 2001, 59(3), 415-419.
[PMID: 11179433]
[80]
Geyer, R.; Buschauer, A. Synthesis and histamine H(3) and H(4) receptor activity of conformationally restricted cyanoguanidines related to UR-PI376. Arch. Pharm. (Weinheim), 2011, 344(12), 775-785.
[PMID: 21987304]
[81]
Lavrador-Erb, K.; Ravula, S.B.; Yu, J.; Zamani-Kord, S.; Moree, W.J.; Petroski, R.E.; Wen, J.; Malany, S.; Hoare, S.R.; Madan, A.; Crowe, P.D.; Beaton, G. The discovery and structure-activity relationships of 2-(piperidin-3-yl)-1H-benzimidazoles as selective, CNS penetrating H1-antihistamines for insomnia. Bioorg. Med. Chem. Lett., 2010, 20(9), 2916-2919.
[PMID: 20347297]
[82]
Ravula, S.B.; Yu, J.; Tran, J.A.; Arellano, M.; Tucci, F.C.; Moree, W.J.; Li, B-F.; Petroski, R.E.; Wen, J.; Malany, S.; Hoare, S.R.; Madan, A.; Crowe, P.D.; Beaton, G. Lead optimization of 2-(piperidin-3-yl)-1H-benzimidazoles: Identification of 2-morpholin- and 2-thiomorpholin-2-yl-1H-benzimidazoles as selective and CNS penetrating H1-antihistamines for insomnia. Bioorg. Med. Chem. Lett., 2012, 22(1), 421-426.
[PMID: 22153347]
[83]
Coon, T.; Moree, W.J.; Li, B.; Yu, J.; Zamani-Kord, S.; Malany, S.; Santos, M.A.; Hernandez, L.M.; Petroski, R.E.; Sun, A.; Wen, J.; Sullivan, S.; Haelewyn, J.; Hedrick, M.; Hoare, S.J.; Bradbury, M.J.; Crowe, P.D.; Beaton, G. Brain-penetrating 2-aminobenzimidazole H(1)-antihistamines for the treatment of insomnia. Bioorg. Med. Chem. Lett., 2009, 19(15), 4380-4384.
[PMID: 19553115]
[84]
Wang, X.J.; Xi, M.Y.; Fu, J.H.; Zhang, F.R.; Cheng, G.F.; You, Q.D. Synthesis, biological evaluation and SAR studies of benzimidazole derivatives as H1-antihistamine agents. Chin. Chem. Lett., 2012, 23(6), 707-710.
[85]
Vasava, M.S.; Bhoi, M.N.; Rathwa, S.K.; Borad, M.A.; Nair, S.G.; Patel, H.D. Drug development against tuberculosis: Past, present and future. Indian J. Tuberc., 2017, 64(4), 252-275.
[PMID: 28941848]
[86]
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.
[87]
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.
[PMID: 19482384]
[88]
Soni, B.; Ranawat, M.S.; Sharma, R.; Bhandari, A.; Sharma, S. Synthesis and evaluation of some new benzothiazole derivatives as potential antimicrobial agents. Eur. J. Med. Chem., 2010, 45(7), 2938-2942.
[PMID: 20413186]
[89]
Zhang, H-Z.; He, S-C.; Peng, Y-J.; Zhang, H-J.; Gopala, L.; Tangadanchu, V.K.R.; Gan, L-L.; Zhou, C-H. Design, synthesis and antimicrobial evaluation of novel benzimidazole-incorporated sulfonamide analogues. Eur. J. Med. Chem., 2017, 136, 165-183.
[PMID: 28494254]
[90]
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.
[PMID: 19540630]
[91]
Camacho, J.; Barazarte, A.; Gamboa, N.; Rodrigues, J.; Rojas, R.; Vaisberg, A.; Gilman, R.; Charris, J. Synthesis and biological evaluation of benzimidazole-5-carbohydrazide derivatives as antimalarial, cytotoxic and antitubercular agents. Bioorg. Med. Chem., 2011, 19(6), 2023-2029.
[PMID: 21334900]
[92]
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, S1125-S1130.
[93]
Soni, B.; Ranawat, M.S.; Bhandari, A.; Verma, R.; Sharma, R.; Prajapat, R.P. Synthesis and Antimicrobial activity of some novel N-substituted-2-substituted benzimidazole derivatives. J. Pharm. Res., 2012, 5(7), 3523-3526.
[94]
White, N.J. Determinants of relapse periodicity in Plasmodium vivax malaria. Malar. J., 2011, 10(1), 297.
[PMID: 21989376]
[95]
Mikolajczak, S.A.; Vaughan, A.M.; Kangwanrangsan, N.; Roobsoong, W.; Fishbaugher, M.; Yimamnuaychok, N.; Rezakhani, N.; Lakshmanan, V.; Singh, N.; Kaushansky, A.; Camargo, N.; Baldwin, M.; Lindner, S.E.; Adams, J.H.; Sattabongkot, J.; Kappe, S.H. Plasmodium vivax liver stage development and hypnozoite persistence in human liver-chimeric mice. Cell Host Microbe, 2015, 17(4), 526-535.
[PMID: 25800544]
[96]
Krotoski, W.A.; Collins, W.E.; Bray, R.S.; Garnham, P.C.; Cogswell, F.B.; Gwadz, R.W.; Killick-Kendrick, R.; Wolf, R.; Sinden, R.; Koontz, L.C.; Stanfill, P.S. Demonstration of hypnozoites in sporozoite-transmitted Plasmodium vivax infection. Am. J. Trop. Med. Hyg., 1982, 31(6), 1291-1293.
[PMID: 6816080]
[97]
Amaratunga, C.; Lim, P.; Suon, S.; Sreng, S.; Mao, S.; Sopha, C.; Sam, B.; Dek, D.; Try, V.; Amato, R.; Blessborn, D.; Song, L.; Tullo, G.S.; Fay, M.P.; Anderson, J.M.; Tarning, J.; Fairhurst, R.M. Dihydroartemisinin-piperaquine resistance in Plasmodium falciparum malaria in Cambodia: A multisite prospective cohort study. Lancet Infect. Dis., 2016, 16(3), 357-365.
[PMID: 26774243]
[98]
Toro, P.; Klahn, A.H.; Pradines, B.; Lahoz, F.; Pascual, A.; Biot, C.; Arancibia, R. Organometallic benzimidazoles: Synthesis, characterization and antimalarial activity. norg. Chem. Commun. (Camb.), 2013, 35, 126-129.
[99]
Farahat, A.A.; Ismail, M.A.; Kumar, A.; Wenzler, T.; Brun, R.; Paul, A.; Wilson, W.D.; Boykin, D.W. Indole and benzimidazole bichalcophenes: Synthesis, DNA binding and antiparasitic activity. Eur. J. Med. Chem., 2018, 143, 1590-1596.
[PMID: 29126729]
[100]
Alpan, A.S.; Sarıkaya, G.; Çoban, G.; Parlar, S.; Armagan, G.; Alptüzün, V. Mannich-Benzimidazole derivatives as antioxidant and anticholinesterase inhibitors: Synthesis, biological evaluations, and molecular docking study. Arch. Pharm. (Weinheim), 2017, 350(7)e1600351
[PMID: 28379621]
[101]
Coban, G.; Carlino, L.; Tarikogullari, A.H.; Parlar, S.; Sarıkaya, G.; Alptüzün, V.; Alpan, A.S.; Güneş, H.S.; Erciyas, E. 1H-benzimidazole derivatives as butyrylcholinesterase inhibitors: Synthesis and molecular modeling studies. Med. Chem. Res., 2016, 25, 2005-2014.
[102]
Mohsen, U.A. Synthesis and biological evaluation of some new benzimidazole derivatives bearing dithiocarbamate moiety as potential cholinesterase inhibitors. Cukurova Med. J., 2014, 39, 729-735.
[103]
Faraji, L.; Shahkarami, S.; Nadri, H.; Moradi, A.; Saeedi, M.; Foroumadi, A.; Ramazani, A.; Haririan, I.; Ganjali, M.R.; Shafiee, A.; Khoobi, M. Synthesis of novel benzimidazole and benzothiazole derivatives bearing a 1, 2, 3-triazole ring system and their acetylcholinesterase inhibitory activity. J. Chem. Res., 2017, 41, 30-35.
[104]
Yoon, Y.K.; Ali, M.A.; Wei, A.C.; Choon, T.S.; Khaw, K.Y.; Murugaiyah, V.; Osman, H.; Masand, V.H. Synthesis, characterization, and molecular docking analysis of novel benzimidazole derivatives as cholinesterase inhibitors. Bioorg. Chem., 2013, 49, 33-39.
[PMID: 23886696]
[105]
El-Gohary, N.S.; Shaaban, M.I. Synthesis, antimicrobial, antiquorum-sensing, and cytotoxic activities of new series of isoindoline-1,3-dione, pyrazolo[5,1a]isoindole and pyridine derivatives. Arch. Pharm. (Weinheim), 2015, 348(9), 666-680.
[PMID: 26081038]
[106]
El-Gohary, N.S.; Shaaban, M.I. Antimicrobial and antiquorum-sensing studies. Part 3: Synthesis and biological evaluation of new series of [1,3,4]thiadiazoles and fused [1,3,4]thiadiazoles. Arch. Pharm. (Weinheim), 2015, 348(4), 283-297.
[PMID: 25773477]
[107]
McClean, K.H.; Winson, M.K.; Fish, L.; Taylor, A.; Chhabra, S.R.; Camara, M.; Daykin, M.; Lamb, J.H.; Swift, S.; Bycroft, B.W.; Stewart, G.S.; Williams, P. Quorum sensing and Chromobacterium violaceum: Exploitation of violacein production and inhibition for the detection of N-acylhomoserine lactones. Microbiology, 1997, 143(Pt 12), 3703-3711.
[PMID: 9421896]
[108]
McLean, R.J.; Pierson, L.S., III; Fuqua, C. A simple screening protocol for the identification of quorum signal antagonists. J. Microbiol. Methods, 2004, 58(3), 351-360.
[PMID: 15279939]
[109]
Chu, W.; Vattem, D.A.; Maitin, V.; Barnes, M.B.; McLean, R.J. Bioassays of quorum sensing compounds using Agrobacterium tumefaciens and Chromobacterium violaceum. Methods Mol. Biol., 2011, 692, 3-19.
[PMID: 21031300]
[110]
El-Gohary, N.S.; Shaaban, M.I. New pyrazolopyridine analogs: Synthesis, antimicrobial, antiquorum-sensing and antitumor screening. Eur. J. Med. Chem., 2018, 152, 126-136.
[PMID: 29702448]
[111]
El-Gohary, N.S.; Shaaban, M.I. Synthesis and biological evaluation of a new series of benzimidazole derivatives as antimicrobial, antiquorum-sensing and antitumor agents. Eur. J. Med. Chem., 2017, 131, 255-262.
[PMID: 28334654]
[112]
El-Gohary, N.S.; Shaaban, M.I. Synthesis, antimicrobial, antiquorum-sensing and antitumor activities of new benzimidazole analogs. Eur. J. Med. Chem., 2017, 137, 439-449.
[PMID: 28623814]
[113]
Parmar, S.S. Symposium on CNS Drugs. CSIR Publication, Hyderabad, India.. 1966, p. 198.
[114]
Parmar, S.S. Antagonism between stereoisomeric amphetamines, amphetamine derivatives and other monoamine oxidase inhibitors. Biochem. Pharmacol., 1966, 15(10), 1497-1505.
[PMID: 4382014]
[115]
Mitra, C.; Guha, S.R. Serotonin oxidation by type B MAO of rat brain. Biochem. Pharmacol., 1980, 29(9), 1213-1216.
[PMID: 6772194]
[116]
Taylor, R.J.; Markley, E.; Ellenbogen, L. The inhibition of monoamine oxidase by styrylquinoliniums. Biochem. Pharmacol., 1967, 16, 79-86.
[117]
Can, Ö.D.; Osmaniye, D.; Demir Özkay, Ü.; Sağlık, B.N.; Levent, S.; Ilgın, S.; Baysal, M.; Özkay, Y.; Kaplancıklı, Z.A. MAO enzymes inhibitory activity of new benzimidazole derivatives including hydrazone and propargyl side chains. Eur. J. Med. Chem., 2017, 131, 92-106.
[PMID: 28301816]
[118]
Mathew, B.; Suresh, J.; Anbazhagan, S. Development of novel (1-H) benzimidazole bearing pyrimidine-trione based MAO-A inhibitors: Synthesis, docking studies and antidepressant activity. J. Saudi Chem. Soc., 2016, 20, S132-S1329.
[119]
Ndakala, A.J.; Gessner, R.K.; Gitari, P.W.; October, N.; White, K.L.; Hudson, A.; Fakorede, F.; Shackleford, D.M.; Kaiser, M.; Yeates, C.; Charman, S.A.; Chibale, K. Antimalarial pyrido[1,2-a] benzimidazoles. J. Med. Chem., 2011, 54(13), 4581-4589.
[PMID: 21644541]
[120]
Barrier Therapeutics, Inc.; Barrier Therapeutics granted European orphan drug status for liarozole, 2003. Available at: . http://www.prnewswire.com/news-releases/71303547.html
[121]
Barrier Therapeutics, Inc. Barrier Therapeutics' liarozole receives FDA orphan drug status,; 2004.Available at:. . http://www.prnewswire.com/news-releases/barrier-therapeutics-liarozole-receives-fda-orphan-drug-status-75105912.html
[122]
Verfaille, C.J.; Borgers, M.; van Steensel, M.A. Retinoic acid metabolism blocking agents (RAMBAs): A new paradigm in the treatment of hyperkeratotic disorders. J. Dtsch. Dermatol. Ges., 2008, 6(5), 355-364.
[PMID: 17941881]
[123]
Wouters, W.; van Dun, J.; Dillen, A.; Coene, M-C.; Cools, W.; De Coster, R. Effects of liarozole, a new antitumoral compound, on retinoic acid-induced inhibition of cell growth and on retinoic acid metabolism in MCF-7 human breast cancer cells. Cancer Res., 1992, 52(10), 2841-2846.
[PMID: 1581897]
[124]
Gordon, S.G.; Miller, M.W.; Saunders, A.B. Pimobendan in heart failure therapy--a silver bullet? J. Am. Anim. Hosp. Assoc., 2006, 42(2), 90-93.
[PMID: 16527909]
[125]
Summerfield, N.J.; Boswood, A.; O’Grady, M.R.; Gordon, S.G.; Dukes-McEwan, J.; Oyama, M.A.; Smith, S.; Patteson, M.; French, A.T.; Culshaw, G.J.; Braz-Ruivo, L.; Estrada, A.; O’Sullivan, M.L.; Loureiro, J.; Willis, R.; Watson, P. Efficacy of pimobendan in the prevention of congestive heart failure or sudden death in Doberman Pinschers with preclinical dilated cardiomyopathy (the PROTECT Study). J. Vet. Intern. Med., 2012, 26(6), 1337-1349.
[PMID: 23078651]
[126]
Lubsen, J.; Just, H.; Hjalmarsson, A.C.; La Framboise, D.; Remme, W.J.; Heinrich-Nols, J.; Dumont, J.M.; Seed, P. Effect of pimobendan on exercise capacity in patients with heart failure: Main results from the Pimobendan in Congestive Heart Failure (PICO) trial. Heart, 1996, 76(3), 223-231.
[PMID: 8868980]
[127]
Ganetsky, M.; Babu, K.M.; Salhanick, S.D.; Brown, R.S.; Boyer, E.W. Dabigatran: Review of pharmacology and management of bleeding complications of this novel oral anticoagulant. J. Med. Toxicol., 2011, 7(4), 281-287.
[PMID: 21887485]
[128]
Pragst, I.; Zeitler, S.H.; Doerr, B.; Kaspereit, F.J.; Herzog, E.; Dickneite, G.; van Ryn, J. Reversal of dabigatran anticoagulation by prothrombin complex concentrate (Beriplex P/N) in a rabbit model. J. Thromb. Haemost., 2012, 10(9), 1841-1848.
[PMID: 22812619]
[129]
Glund, S.; Stangier, J.; Schmohl, M.; Moschetti, V.; Haazen, W.; De Smet, M.; Gansser, D.; Norris, S.; Lang, B.; Reilly, P. Idarucizumab, a specific antidote for dabigatran: Immediate, complete and sustained reversal of dabigatran induced anticoagulation in elderly and renally impaired subjects. Am. Soc. Hematology, 2014, 344.
[130]
Meijer, D.K.; Hovinga, G.; Versluis, A.; Bröring, J.; van Aken, K.; Moolenaar, F.; Wesseling, H. Pharmacokinetics of the oral narcotic analgesic bezitramide and preliminary observations on its effect on experimentally induced pain. Eur. J. Clin. Pharmacol., 1984, 27(5), 615-618.
[PMID: 6519169]
[131]
Karim, A.; Heykants, J. Metabolism of synthetic antidiarrheal drugs diphenoxylate, difenoxine, and loperamide. Synthetic Antidiarrheal Drugs; M. Dekker, Inc: New York, 1976, pp. 132-154.
[132]
Janssen, P.A.; Niemegeers, C.J.; Schellekens, K.H.; Marsboom, R.H.; Herin, V.V.; Amery, W.K.; Admiraal, P.V.; Bosker, J.T.; Crul, J.F.; Pearce, C.; Zegveld, C. Bezitramide (R 4845), a new potent and orally long-acting analgesic compound. Arzneimittelforschung, 1971, 21(6), 862-867.
[PMID: 5109278]
[133]
Meijer, D.K.; Hovinga, G.; Versluis, A.; Bröring, J.; van Aken, K.; Moolenaar, F.; Wesseling, H. Pharmacokinetics of the oral narcotic analgesic bezitramide and preliminary observations on its effect on experimentally induced pain. Eur. J. Clin. Pharmacol., 1984, 27(5), 615-618.
[PMID: 6519169]

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