Structure activity relationship (SAR) study of benzimidazole scaffold for different biological activities: A mini-review

European Journal of Medicinal Chemistry

Volumn 97, Issue 1, 2015, Pages 419-443

  Yadav, Geeta ^a   Ganguly, Swastika ^a  

^a BIRLA INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Anthelmintics; Benzimidazole; Heterocyclic ring systems; Pharmacological activities; SAR study

Indexed keywords

AGGRECANASE 2; ANALGESIC AGENT; ANTHELMINTIC AGENT; ANTIBIOTIC AGENT; ANTICONVULSIVE AGENT; ANTIDIABETIC AGENT; ANTIINFLAMMATORY AGENT; ANTIMYCOBACTERIAL AGENT; ANTINEOPLASTIC AGENT; ANTIOXIDANT; ANTIPROTOZOAL AGENT; ANTIVIRUS AGENT; ATYPICAL ANTIPSYCHOTIC AGENT; BENZIMIDAZOLE DERIVATIVE; METALLOPROTEINASE INHIBITOR; BENZIMIDAZOLE;

ANTHELMINTIC ACTIVITY; ANTICONVULSANT ACTIVITY; ANTIDIABETIC ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ANTIPROTOZOAL ACTIVITY; ANTIVIRAL ACTIVITY; BIOLOGICAL ACTIVITY; CHEMICAL ANALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; MEDICAL INFORMATION; MEDICINAL CHEMISTRY; MOLECULAR DOCKING; OXIDATIVE STRESS; PHYSICAL CHEMISTRY; REVIEW; STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DEVELOPMENT;

ANIMALS; BENZIMIDAZOLES; DRUG DISCOVERY; HUMANS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84937431709     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.11.053     Document Type: Short Survey

References (87)

1. R.M. Acheson, An Introduction to the Chemistry of Heterocyclic Compounds, third ed., Wiley India Pvt Ltd New Delhi, 2008, pp. 1-3.
2. C.M. Smith, History of benzimidazole use and resistance, in: C.J. Delp (Ed.), Fungicide Resistance in North America, American Phytopathological Society, St Paul MN, 1988, pp. 23-24.
3. T.D. Penning, G.D. Zhu, V.B. Gandhi, J. Gong, X. Liu, Y. Shi, V. Klinghofer, E.F. Johnson, C.K. Donawho, D.J. Frost, V.B. Diaz, J.J. Bouska, D.J. Osterling, A.M. Olson, K.C. Marsh, Y. Luo, V.L. Giranda, Discovery of the poly(ADP-ribose) polymerase (PARP) inhibitor 2-[(R)-2-methylpyrrolidin-2-yl]-1H-benzimidazole-4-carboxamide (ABT-888) for the treatment of cancer, J. Med. Chem. 52 (2009) 514-523.
4. H.M. Refaat, Synthesis and anticancer activity of some novel 2-substituted benzimidazole derivatives, Eur. J. Med. Chem. 45 (2010) 2949-2956.
5. A.R. Castro, I.L. Rivera, L.C. Rojas, G.N. Vazquez, A.N. Rodríguez, Synthesis and preliminary evaluation of selected 2-aryl-5(6)-nitro-1H-benzimidazole derivatives as potential anticancer agents, Arch. Pharm. Res. 34 (2011) 181-189.
6. R. Abonia, E. Cortes, B. Insuasty, J. Quiroga, M. Nogueras, J. Cobo, Synthesis of novel 125-trisubstituted benzimidazoles as potential antitumor agents, Eur. J. Med. Chem. 46 (2011) 4062-4070.
7. H.T.A. Mohsen, F.A.F. Ragab, M.M. Ramla, H.I.E. Diwani, Novel benzimidazole pyrimidine conjugates as potent anti-tumor agents, Eur. J. Med. Chem. 45 (2010) 2336-2344.
8. S. Demirayak, I. Kayagil, L. Yurttas, Microwave supported synthesis of some novel 13-diarylpyrazino[12-a]benzimidazole derivatives and investigation of their anticancer activities, Eur. J. Med. Chem. 46 (2011) 411-416.
9. S. Demirayak, A. Usama, A.C. Mohsen, K. Agri, Synthesis and anticancer and anti-HIV testing of some pyrazino[12-a]benzimidazole derivatives, Eur. J. Med. Chem. 37 (2002) 255-260.
10. A.G. Shadia, H.H. Khaled, S.K. Ahmed, L.R. Mireya, M.K. Sean, M.A. Abdel, I.E. Hoda, New transition metal ion complexes with benzimidazole-5-carboxylic acid hydrazides with antitumor activity, Eur. J. Med. Chem. 44 (2009) 1500-1508.
11. A.G. Shadia, H.H. Khaled, M.H. Ahmed, S.Y. Nabil, Synthesis and antitumor activity of novel benzimidazole-5-carboxylic acid derivatives and their transition metal complexes as topoisomerease II inhibitors, Eur. J. Med. Chem. 45 (2010) 5685-5691.
12. A. Kamal, P. Praveen Kumar, K. Sreekanth, B.N. Seshadri, P. Ramulu, Synthesis of new benzimidazole linked pyrrolo [2 1-c][1 4] benzodiazepine conjugates with efficient DNA-binding affinity and potent cytotoxicity, Bioorg. Med. Chem. Lett. 18 (2008) 2594-2598.
13. N.R. Gowda, C.V. Kavitha, K.K. Chiruvella, O. Joy, K.S. Rangappa, S.C. Raghavan, Synthesis and biological evaluation of novel 1-(4-methoxyphenethyl)-1Hbenzimidazole-5-carboxylic acid derivatives and their precursors as antileukemic agents, Bioorg. Med. Chem. Lett. 19 (2009) 4594-4600.
14. E. Moriarty, M. Carr, S. Bonham, M.P. Carty, F. Aldabbagh, Synthesis and toxicity towards normal and cancer cell lines of benzimidazole quinones containing fused aromatic rings and 2-aromatic ring substituents, Eur. J. Med. Chem. 45 (2010) 3762-3769.
15. B.V.S. Kumar, S.D. Vaidya, R.V. Kumar, S.B. Bhirud, R.B. Mane, Synthesis and anti-bacterial activity of some novel 2-(6-fluorochroman-2-yl)-1-alkyl/acyl/aroyl-1H-benzimidazoles, Eur. J. Med. Chem. 41 (2006) 599-604.
16. K.M. Hosamani, H.R. Seetharamareddy, R.S. Keri, M.S. Hanamanthagouda, M.G. Moloney, Microwave assisted one-pot synthesis of 5-nitro-2-aryl substituted-1H-benzimidazole libraries: screening in vitro for antimicrobial activity, J. Enzy. Inhibi. Med. Chem. 24 (2009) 1095-1100.
17. G.A. Kilcig, N. Altanlar, Synthesis and antifungal activity of some benzimidazole derivatives, Turk. J. Chem. 30 (2006) 223-228.
18. I. Kerimov, A.G. Kilcgil, B.C. Eke, N. Altanlar, M.J. Iscan, Synthesis antifungal and antioxidant screening of some novel benzimidazole derivatives, Enzy. Inhibi. Med. Chem. 22 (2007) 696-701.
19. D. Sharma, B. Narasimhan, P. Kumar, V. Judge, R. Narang, E.D. Clercq, J.J. Balzarini, Synthesis antimicrobial and antiviral activity of substituted benzimidazoles, Enzy. Inhibi. Med. Chem. 24 (2009) 1161.
20. H. Goker, C. Kus, D.W. Boykin, S. Yildiz, N. Altanlar, Synthesis of some new 2-substituted-phenyl-1H-benzimidazole-5-carbonitriles and their potent activity against Candida species, Bioorg. Med. Chem. 10 (2002) 2589-2596.
21. C. Kus, A.G. Kilcgil, B.C. Eke, M. Iscan, Synthesis and antioxidant properties of some novel benzimidazole derivatives on lipid peroxidation in the rat liver, Arch. Pharm. Res. 27 (2004) 156-163.
22. G.A. Kilcgil, N. Altanlar, Synthesis and antimicrobial activities of some new benzimidazole derivatives, IL Farm. 58 (2003) 1345-1350.
23. C. Kus, G.A. Kilcgil, S. Ozbey, F.B. Kaynak, M. Kaya, T. Coban, B.C. Eke, Synthesis and antioxidant properties of novel N-methyl-134-thiadiazol-2-amine and 4-methyl-2H-124-triazole-3(4H)-thione derivatives of benzimidazole class, Bioorg. Med. Chem. 16 (2008) 4294-4303.
24. P. Francisca, J.C. Helgi, P.V. Jaime, C.P. Juan, R.M. Sergio, P.H. Guadalupe, L.B. Nayeli, H.C. Alicia, C. Rafael, H.L. Francisco, Synthesis and in vitro cysticidal activity of new benzimidazole derivatives, Eur. J. Med. Chem. 44 (2009) 1794-1800.
25. J.B. Wright, Chemistry of benzimidazoles, Chem. Rev. 48 (1951) 397.
26. T.B. Nguyen, L. Ermolenko, W.A. Dean, A. Al-Mourabit, Benzazoles from aliphatic amines and o-Amino/Mercaptan/Hydroxyanilines: elemental sulfur as a highly efficient and traceless oxidizing agent, Org. Lett. 4 (2012) 5948-5951.
27. E.J. Hanan, B.K. Chan, A.A. Estrada, D.G. Shore, J.P. Lyssikatos, Mild and general one-pot reduction and cyclization of aromatic and heteroaromatic 2-nitroamines to bicyclic 2H-imidazoles, Synlett 18 (2010) 2759-2764.
28. D. Yang, D. Fokas, J. Li, L. Yu, C.M. Baldino, A versatile method for the synthesis of benzimidazoles from o-nitroanilines and aldehydes in one step via a reductive cyclization, Synthesis 1 (2005) 47-56.
29. W. Cui, R.B. Kargbo, Z. Sajjadi-Hashemi, F. Ahmed, J.F. Gauuan, Efficient onepot synthesis of 2-substituted benzimidazoles from triacyloxyborane intermediates, Synlett 23 (2012) 247-250.
30. J. Sluiter, J. Christoffers, Synthesis of 1-methylbenzimidazoles from carbonitriles, Synlett 1 (2009) 63-66.
31. B.C. Wray, J.P. Stambuli, Synthesis of N-arylindazoles and benzimidazoles from a common intermediate, Org. Lett. 12 (2010) 4576-4579.
32. J. Peng, M. Ye, C. Zong, F. Hu, L. Feng, X. Wang, Y. Wang, C. Chen, Coppercatalyzed intramolecular c-N bond formation: a straightforward synthesis of benzimidazole derivatives in water, J. Org. Chem. 76 (2010) 716-719.
33. P. Saha, T. Ramana, N. Purkait, M.A. Ali, R. Paul, T. Punniyamurthy, Ligand-free copper-catalyzed synthesis of substituted benzimidazoles 2-aminobenzimidazoles 2-aminobenzothiazoles and benzoxazoles, J. Org. Chem. 74 (2009) 8719-8725.
34. X. Diao, Y. Wang, Y. Jiang, D. Ma, Assembly of substituted 1 H-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. 74 (2009) 7974-7977.
35. Y. Kim, M.R. Kumar, N. Park, Y. Heo, S. Lee, Copper-catalyzed one-pot threecomponent synthesis of benzimidazoles by condensation and C-N bond formation, J. Org. Chem. 76 (2011) 9577-9583.
36. K. Bahrami, M.M. Khodaei, I. Kavianinia, A simple and efficient one-pot synthesis of 2-substituted benzimidazoles, Synthesis (2007) 417-427.
37. L.H. Du, Y.G. Wang, A rapid and efficient synthesis of benzimidazoles using hypervalent iodine as oxidant, Synthesis 5 (2007) 675-678.
38. P.L. Beaulieu, B. Haché, E. Von Moos, A practical oxone®-mediated highthroughput solution-phase synthesis of benzimidazoles from 1 2-phenylenediamines and aldehydes and its application to preparative scale synthesis, Synthesis 11 (2003) 1683-1692.
39. B.C. Venkatesh, C. Premakumari, A. Padmaja, V. Padmavathi, Polarized ketene dithiolates-versatile synthons for different heterocycles, Chin. J. Chem. 30 (2012) 1886-1892.
40. G. Bastug, C. Eviolitte, I.E. Markó, Functionalized orthoesters as powerful building blocks for the efficient preparation of heteroaromatic bicycles, Org. Lett. 14 (2012) 3502-3505.
41. S. Caron, B.P. Jones, L. Wei, Preparation of substituted benzimidazoles and imidazopyridines using 2 2 2-trichloroethyl imidates, Synthesis (2012) 3049-3054.
42. K. Bahrami, M.M. Khodaei, F. Naali, Mildand highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles, J. Org. Chem. 73 (2008) 6835-6837.
43. J. She, Z. Jiang, Y. Wang, One-pot synthesis of functionalized benzimidazoles and 1H-pyrimidines via cascade reactions of o-amino anilines or naphthalene-18-diamine with alkynes and p-tolylsulfonyl azide, Synlett (2009) 2023-2027.
44. X. Lv, W. Bao, Copper-catalyzed cascade addition/cyclization: an efficient and versatile synthesis of N-substituted 2-heterobenzimidazoles, J. Org. Chem. 74 (2009) 5618-5621.
45. Y. Luo, J.P. Yao, L. Yang, C.L. Feng, W. Tang, G.F. Wang, W. Lu, Design and synthesis of novel benzimidazole derivatives as inhibitors of hepatitis B virus, Bioorg. Med. Chem. 18 (2010) 5048-5055.
46. K.S. Gudmundsson, P.R. Sebahar, L.D. Richardson, J.F. Miller, E.M. Turner, J.G. Catalano, A. Spaltenstein, W. Lawrence, M. Thomson, S. Jenkinson, Amine substituted N-(1H-benzimidazol-2ylmethyl)-5678-tetrahydro-8-quinolinamines as CXCR4 antagonists with potent activity against HIV-1, Bioorg. Med. Chem. Lett. 19 (2009) 5048-5052.
47. J.E. Miller, E.M. Turner, A.S. Gudmundsson, S. Jenkinson, A. Spaltenstein, N. Thomsan, P. Wheelan, Bioorg. Med. Chem. Lett. 20 (2010) 2125-2128.
48. P.L. Beaulieu, N. Dansereau, J. Duan, M. Garneau, J. Gillard, G. McKercher, S. LaPlante, L. Lagacee, L. Thauvette, G. Kukolj, Bioorg. Med. Chem. Lett. 20 (2010) 1825-1829.
49. M. Tonelli, M. Simone, B. Tasso, F. Novelli, V. Boido, F. Sparatore, G. Paglietti, S. Prici, G. Giliberti, S. Blois, C. Ibba, G. Sanna, R. Laddo, P.L. Colla, Antiviral activity of benzimidazole derivatives II antiviral activity of 2-phenylbenzimidazole derivatives, Bioorg. Med. Chem. 18 (2010) 2937-2953.
50. R. Wubulikasimu, Y. Yang, F. Xue, X. Luo, D. Shao, Y. Li, W. Ye, Synthesis and biological evaluation of novel benzimidazole derivatives bearing a heterocyclic ring at 4/5 position, Bull. Korean Chem. Soc. 34 (2013) 2297-2304.
51. A-M. Monforte, S. Ferro, L.D. Luca, G. L. Surdo, F. Morreale, C. Pannecouque, J. Balzarini and A. Chimirri, Design and synthesis of N1-aryl-benzimidazoles 2-substituted as novel HIV-1 nonnucleoside reverse transcriptase inhibitors. Accepted manuscript http://dxdoiorg/101016/jbmc201312045.
52. P. Xiang, T. Zhou, L. Wang, C.Y. Sun, J. Hu, Y.L. Zhao, L. Yang, Novel benzothiazole benzimidazole and benzoxazole derivatives as potential antitumor agents: synthesis and preliminary in vitro biological evaluation, Molecules 17 (2012) 873-883.
53. M.A. Omar, Y.M. Shaker, S.A. Galal, M.M. Ali, S.M. Kerwin, J. Li, H.I. El Diwani, Synthesis and docking studies of novel antitumor benzimidazoles, Bioorg. Med. Chem. 20 (2012) 6989-7001.
54. T. Liu, C. Sun, X. Xing, L. Jing, R. Tan, Y. Luo, Y. Zhao, Synthesis and evaluation of 2-[2-(phenylthiomethyl)-1H-benzo [d] imidazol-1-yl) acetohydrazide derivatives as antitumor agents, Bioorg. Med. Chem. Lett. 22 (2012) 3122-3125.
55. C. Karthikeyan, V.R. Solomon, H. Lee, P. Trivedi, Synthesis and biological evaluation of 2-(phenyl)-3H-benzo [d] imidazole-5-carboxylic acids and its methyl esters as potent anti-breast cancer agents, Arab. J. Chem. (2013) xxx xxx-xxx Article in press.
56. Y.K. Yoon, M.A. Ali, A.C. Wei, T.S. Choon, H. Osman, K. Parang, A.N. Shirazi, Synthesis and evaluation of novel benzimidazole derivatives as sirtuin inhibitors with antitumor activities, Bioorg. Chem. Med. 22 (2014) 703-710.
57. H.B. El-Nassan, Synthesis antitumor activity and SAR study of novel [1 2 4] triazino [4 5-a] benzimidazole derivatives, Eur. J. Med. Chem. 53 (2012) 22-27.
58. M. Singh, V. Tandon, Synthesis and biological activity of novel inhibitors of topoisomerase I: 2-Aryl-substituted 2-bis-1H-benzimidazoles, Eur. J. Med. Chem. 46 (2011) 659-669.
59. R. Sawant, D. Kawade, Synthesis and biological evaluation of some novel 2-phenyl benzimidazole-1-acetamide derivatives as potential anthelmintic agents, Acta Pharm. 61 (2011) 353-361.
60. Y.K. Yoon, M.A. Ali, T.S. Choon, R. Ismail, A.C. Wei, R.S. Kumar, H. Osman, F. Beevi, Antituberculosis: synthesis and antimycobacterial activity of novel benzimidazole derivatives, Biomed. Res. Inter. (2013) 6. Article ID 926309.
61. K. Gobis, H. Foks, K. Bojanowski, E. Augustynowicz-Kopeć, A. Napiórkowska, Synthesis of novel 3-cyclohexylpropanoic acid-derived nitrogen heterocyclic compounds and their evaluation for tuberculostatic activity, Bioorg. Med. Chem. 20 (2012) 137-144.
62. B. Zhou, B. Li, W. Yi, X. Bu, L. Ma, Synthesis antioxidant and antimicrobial evaluation of some 2-arylbenzimidazole derivatives, Bioorg. Med. Chem. Lett. 23 (2013) 3759-3763.
63. D. Joshi, K. Parikh, Synthesis and evaluation of novel benzimidazole derivatives as antimicrobial agents, Med. Chem. Res. 23 (2014) 1290-1299.
64. H.H. Jardosh, C.B. Sangani, M.P. Patel, R.G. Patel, One step synthesis of pyrido 1 2-a benzimidazole derivatives of aryloxypyrazole and their antimicrobial evaluation, Chin. Chem. Lett. 24 (2013) 123-126.
65. B. Garudachari, M.N. Satyanarayana, B. Thippeswamy, C.K. Shivakumar, K.N. Shivananda, G. Hegde, A.M. Isloor, Synthesis characterization and antimicrobial studies of some new quinoline incorporated benzimidazole derivatives, Eur. J. Med. Chem. 54 (2012) 900-906.
66. P.K. Ranjith, P. Rajeesh, K.R. Haridas, N.K. Susanta, T.N. Guru Row, R. Rishikesan, N. Suchetha Kumari, Design and synthesis of positional isomers of 5 and 6-bromo-1-[(phenyl) sulfonyl]-2-[(4-nitrophenoxy) methyl]-1Hbenzimidazoles as possible antimicrobial and antitubercular agents, Bioorg. Med. Chem. 23 (2013) 5228-5234.
67. D. Zhang, Z. Wang, W. Xu, F. Sun, L. Tang, J. Wang, Design synthesis and antibacterial activity of novel actinonin derivatives containing benzimidazole heterocycles, Eur. J. Med. Chem. 44 (2009) 2202-2210.
68. Y. Özkay, Y. Tunali, H. Karaca, I. Iş ikdaʇ, Antimicrobial activity and a SAR study of some novel benzimidazole derivatives bearing hydrazone moiety, Eur. J. Med. Chem. 45 (2010) 3293-3298.
69. D. Seenaiah, P. Ramachandra Reddy, G. Mallikarjuna Reddy, A. Padmaja, V. Padmavathi, N. Siva krishna, Synthesis, antimicrobial and cytotoxic activities of pyrimidinyl benzoxazole, benzothiazole and benzimidazole, Eur. J. Med. Chem. 77 (2014) 1-7.
70. S. Ganguly, G. Yadav, Molecular docking studies of novel benzimidazole analogs as HIV-1-RT inhibitors with broad spectrum chemotherapeutic properties, Int. J. Drug Des. Dis 4 (2013).
71. G. Yadav, S. Ganguly, S. Murugesan, A. Dev, Synthesis, Anti-HIV, Antimicrobial Evaluation and Structure Activity Relationship Studies of Some Novel Benzimidazole Derivatives Anti-Infective Agents, 2014 (Accepted).
72. R.V. Shingalapur, K.M. Hosamani, R.S. Keri, M.H. Hugar, Derivatives of benzimidazole pharmacophore: synthesis anticonvulsant antidiabetic and DNA cleavage studies, Eur. J. Med. Chem. 45 (2010) 1753-1759.
73. K. Achar, K.M. Hosamani, H.R. Seetharamareddy, In-vivo analgesic and antiinflammatory activities of newly synthesized benzimidazole derivatives, Eur. J. Med. Chem. 45 (2010) 2048-2054.
74. A.O. El-Nezhawy, A.R. Biuomy, F.S. Hassan, A.K. Ismaiel, H.A. Omar, Design synthesis and pharmacological evaluation of omeprazole-like agents with anti-inflammatory activity, Bioorg. Med. Chem. 21 (2013) 1661-1670.
75. M. Ishikawa, K. Nonoshita, Y. Ogino, Y. Nagae, D. Tsukahara, H. Hosaka, H. Hosaka, H. Maruki, S. Ohyama, R. Yoshimoto, K. Sasaki, Y. Nagata, T. Nishimura, Discovery of novel 2-(pyridine-2-yl)-1H-benzimidazole derivatives as potent glucokinase activators, Bioorg. Med. Chem. Lett. 19 (2009) 4450-4454.
76. H.J. Kwak, Y.M. Pyun, J.Y. Kim, H.S. Pagire, K.Y. Kim, K.R. Kim, S.D. Rhee, W.H. Jung, J.S. Song, M.A. Bae, D.H. Lee, J.H. Ahn, Synthesis and biological evaluation of aminobenzimidazole derivatives with a phenylcyclohexyl acetic acid group as anti-obesity and anti-diabetic agents, Bioorg. Med. Chem. Lett. 23 (2013) 4713-4718.
77. D. Valdez-Padilla, S. Rodríguez-Morales, A. Hernández-Campos, F. Hernández-Luis, L. Yépez-Mulia, A. Tapia-Contreras, R. Castillo, Synthesis and antiprotozoal activity of novel 1-methylbenzimidazole derivatives, Bioorg. Med. Chem. 17 (2009) 1724-1730.
78. Z.S. Saify, M.K. Azim, W. Ahmad, M. Nisa, D.E. Goldberg, S.A. Hussain, S. Akhtar, A. Akram, A. Arayne, A. Oksman, I.A. Khan, New benzimidazole derivatives as antiplasmodial agents and plasmepsin inhibitors: synthesis and analysis of structure-activity relationships, Bioorg. Med. Chem. Lett. 22 (2012) 1282-1286.
79. R. Aguayo-Ortiz, J. Pérez-Villanueva, A. Hernández-Campos, R. Castillo, N. Meurice, J.L. Medina-Franco, Chemoinformatic characterization of activity and selectivity switches of antiprotozoal compounds, Future Med. Chem. 6 (2014) 281-294.
80. J. Pérez-Villanueva, A. Hernández-Campos, L. Yépez-Mulia, C. Méndez-Cuest, O. Méndez-Lucio, F. Hernández-Luis, R. Castillo, Synthesis and antiprotozoal activity of novel 2-{[2-(1H-imidazol-1-yl)ethyl]sulfanyl}-1H-benzimidazole derivatives, Bioorg. Med. Chem. Lett. 23 (2013) 4221-4224.
81. S. Sogame, Y. Suenaga, M. Atobe, M. Kawanishi, E. Tanaka, S. Miyoshi, Discovery of a benzimidazole series of ADAMTS-5 (aggrecanase-2) inhibitors by scaffold hopping, Eur. J. Med. Chem. 71 (2014) 250-258.
82. W. Hamaguchi, N. Masuda, M. Isomura, S. Miyamoto, S. Kikuchi, Y. Amano, K. Honbou, T. Mihara, T. Watanabe, Design and synthesis of novel benzimidazole derivatives as phosphodiesterase 10A inhibitors with reduced CYP1A2 inhibition, Bioorg. Med. Chem. 21 (2013) 7612-7623.
83. J. Zhu, C.F. Wu, X. Li, G.S. Wu, S. Xie, Q.N. Hu, Z. Deng, M.X. Zhu, H. Luo, X. Hong, Synthesis biological evaluation and molecular modeling of substituted 2-aminobenzimidazoles as novel inhibitors of acetylcholinesterase and butyrylcholinesterase, Bioorg. Med. Chem. Lett. 21 (2013) 4218-4224.
84. Y. Tamura, N. Omori, N. Kouyama, Y. Nishiura, K. Hayashi, K. Watanabe, Y. Tanaka, T. Chiba, H. Yukioka, H. Sato, T. Okuno, Design synthesis and identification of novel benzimidazole derivatives as highly potent NPY Y5 receptor antagonists with attractive in vitro ADME profiles, Bioorg. Med. Chem. Lett. 22 (2012) 5498-5502.
85. V. Padmavathi, B.C. Venkatesh, A. Muralikrishna, A. Padmaja, The reactivity of Gem cyanoester ketene dithiolates towards the development of potent antioxidant heterocycles, Chem. Pharm. Bull. 60 (2012) 449-458.
86. S. Durgamma, A. Muralikrishna, V. Padmavathi, A. Padmaja, Synthesis and antioxidant activity of amido-linked benzoxazolyl/benzothiazolyl/benzimidazolyl-pyrroles and pyrazoles, Med. Chem. Res. 23 (2014) 2916-2929.
87. V. Padmavathi, B.C. Venkatesh, A. Muralikrishna, A. Padmaja, Synthesis and antioxidant activity of a new class of bis and tris heterocycles, Arch. Pharm. Chem. Life Sci. 0 (2012) 1-8.