Design, synthesis and antimicrobial evaluation of novel benzimidazole type of Fluconazole analogues and their synergistic effects with Chloromycin, Norfloxacin and Fluconazole

European Journal of Medicinal Chemistry

Volumn 64, Issue , 2013, Pages 329-344

  Zhang, Hui Zhen ^a   Damu, Guri L V ^a   Cai, Gui Xin ^a   Zhou, Cheng He ^a  

^a SOUTHWEST UNIVERSITY   (China)

Author keywords

Antibacterial; Antifungal; Benzimidazole; Chloromycin; Fluconazole; Norfloxacin

Indexed keywords

7 [6 [[(1H BENZO[D]IMIDAZOL 2YL)METHYL](4 FLUOROPHENYL)AMINO]HEXYLOXY] 4 METHYL 1H CHROMEN 2 ONE; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; BENZIMIDAZOLE DERIVATIVE; CHLOROMYCIN; FLUCONAZOLE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] 2 FLUOROANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] 2,4 DICHLOROANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] 2,4 DIFLUOROANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] 3 TRIFLUOROMETHYL)ANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] 3,5 BIS(TRIFLUOROMETHYL)ANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] 4 CHLOROANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] 4 FLUOROANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] 4 IODOANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] 4 METHYL N OCTADECYLANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] 4 METHYL N OCTYLANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] 4 METHYL N PROPYLANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] 4 METHYLANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] N (2 CHLOROBENZYL) 4 METHYLANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] N (2,4 DICHLOROBENZYL) 3 (TRIFLUOROMETHYL) ANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] N (2,4 DICHLOROBENZYL) 4 FLUOROANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] N (2,4 DIFLUOROBENZYL) 3,5 BIS (TRILFUOROMETHYL)ANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] N (3 CHLOROBENZYL) 4 METHYLANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] N (3,4 DICHLOROBENZYL) 2 FLUOROANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] N (4 CHLOROBENZYL) 4 METHYLANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] N DECYL 4 METHYLANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] N DODECYL 4 METHYLANILINE; N [(1H BENZO[D]IMIDAZOL 2 YL)METHYL)] N HEXYL 4 METHYLANILINE; NORFLOXACIN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS FLAVUS; BACILLUS SUBTILIS; CANDIDA ALBICANS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; COVALENT BOND; DRUG EFFICACY; DRUG POTENTIATION; DRUG SYNTHESIS; ESCHERICHIA COLI; HYDROPHILICITY; INFRARED SPECTROSCOPY; LIPOPHILICITY; MASS SPECTROMETRY; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MICROCOCCUS LUTEUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PROTEUS VULGARIS; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; SACCHAROMYCES CEREVISIAE; SALMONELLA TYPHI; STAPHYLOCOCCUS AUREUS;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; BACTERIA; BENZIMIDAZOLES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG SYNERGISM; FLUCONAZOLE; FUNGI; MICROBIAL SENSITIVITY TESTS; NORFLOXACIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84877021791     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.03.049     Document Type: Article

References (45)

1. H.T. Ji, W.N. Zhang, M. Zhang, M. Kudo, Y. Aoyama, Y. Yoshida, C.Q. Sheng, Y.L. Song, S. Yang, Y.J. Zhou, J.G. Lv, and J. Zhu J. Med. Chem. 46 2003 474 485
2. K. Wan, Y.Y. Zhang, C.H. Zhou, X.D. Zhou, R.X. Geng, and Q.G. Ji Chin. J. Antibiot. 37 2012 8 15 (in Chinese)
3. Y. Wang, and C.H. Zhou Sci. Sin. Chim. 41 2011 1429 1456 (in Chinese)
4. C.H. Zhou, and Y. Wang Curr. Med. Chem. 19 2012 239 280
5. Y.Y. Zhang, J.L. Mi, C.H. Zhou, and X.D. Zhou Eur. J. Med. Chem. 46 2011 4391 4402
6. Y. Wang, G.L.V. Damu, J.S. Lv, R.X. Geng, D.C. Yang, and C.H. Zhou Bioorg. Med. Chem. Lett. 22 2012 5363 5366
7. C.Q. Sheng, and W.N. Zhang Curr. Med. Chem. 18 2011 733 766
8. A.C. Pasqualotto, K.O. Thiele, and L.Z. Goldani Curr. Opin. Invest. Drugs 11 2010 165 174
9. M.T. Fera, E. La Camera, and A. De Sarro Expert Rev. Anti Infect. Ther. 7 2009 981 998
10. G. Thomas Medicinal Chemistry: an Introduction second ed. 2008 John Wiley & Sons New York
11. B. Fang, C.H. Zhou, and X.C. Rao Eur. J. Med. Chem. 45 2010 4388 4398
12. H.T. Ji, W.N. Zhang, Y.J. Zhou, M. Zhang, J. Zhu, Y.L. Song, J.G. Lv, and J. Zhu J. Med. Chem. 43 2000 2493 2505
13. H. Bendaha, L. Yu, R. Touzani, R. Souane, G. Giaever, C. Nislow, C. Boone, S.E. Kadiri, G.W. Brown, and M. Benllaoui Eur. J. Med. Chem. 46 2011 4117 4121
14. S.L. Zhang, J.J. Chang, G.L.V. Damu, B. Fang, X.D. Zhou, R.X. Geng, and C.H. Zhou Bioorg. Med. Chem. Lett. 23 2013 1008 1012
15. M.S. Kedar, N.S. Dighe, S.R. Pattan, D.S. Musmade, D. Thakur, M. Bhosale, and V.M. Gaware Der Pharm. Chem. 2 2010 249 256
16. R. Sivakumar, R. Pradeepchandran, K.N. Jayaveera, P. Kumarnallasivan, P.R. Vijaianand, and R. Venkatnarayanan Int. J. Pharm. Res. 3 2011 19 31
17. J.P. Meng, R.X. Geng, C.H. Zhou, and L.L. Gan Chin. J. New Drugs 18 2009 1505 1514 (in Chinese)
18. J.P. Meng, Y.H. Lu, I. Halqam, and C.H. Zhou Chin. J. Biochem. Pharm. 29 2008 418 421 (in Chinese)
19. S.L. Zhang, G.L.V. Damu, L. Zhang, R.X. Geng, and C.H. Zhou Eur. J. Med. Chem. 55 2012 164 175
20. L. Srikanth, V.V. Raj, N. Raghunandan, and L. Venkateshwerlu Pharma Chem. 3 2011 172 193
21. S. Jubie, R. Rajeshkumar, B. Yellareddy, G. Siddhartha, M. Sandeep, K. Surendrareddy, H.S. Dushyanth, and K. Elango J. Pharm. Sci. Res. 2 2010 69 76
22. B. Narasimhan, D. Sharma, and P. Kumar Med. Chem. Res. 21 2012 269 283
23. D.T. Zhang, Z.H. Wang, W.R. Xu, F.G. Sun, L.D. Tang, and J.W. Wang Eur. J. Med. Chem. 44 2009 2202 2221
24. Y.Y. Zhang, and C.H. Zhou Bioorg. Med. Chem. Lett. 21 2011 4349 4352
25. Q.P. Wang, J.Q. Zhang, G.L.V. Damu, K. Wan, H.Z. Zhang, and C.H. Zhou Sci. China Chem. 55 2012 2134 2153
26. Y. Luo, Y.H. Lu, L.L. Gan, C.H. Zhou, J. Wu, R.X. Geng, and Y.Y. Zhang Arch. Pharm. (Weinheim) 342 2009 386 393
27. X.L. Wang, K. Wan, and C.H. Zhou Eur. J. Med. Chem. 45 2010 4631 4639
28. L.L. Gan, B. Fang, and C.H. Zhou Bull. Korean Chem. Soc. 31 2010 3684 3692
29. K. Wan, and C.H. Zhou Bull. Korean Chem. Soc. 31 2010 2003 2010
30. F.F. Zhang, C.H. Zhou, and J.P. Yan Chin. J. Org. Chem. 30 2010 783 796 (in Chinese)
31. F.F. Zhang, L.L. Gan, and C.H. Zhou Bioorg. Med. Chem. Lett. 20 2010 1881 1884
32. Y. Shi, and C.H. Zhou Bioorg. Med. Chem. Lett. 21 2011 956 960
33. Y. Shi, C.H. Zhou, X.D. Zhou, R.X. Geng, and Q.G. Ji Acta Pharm. Sin. 46 2011 798 810 (in Chinese)
34. A. Rosato, M. Piarulli, F. Corbo, M. Muraglia, A. Carone, M.E. Vitali, and C. Vitali Curr. Med. Chem. 17 2010 3289 3295
35. J.P. Demchok, J. Meletiadis, E. Roilides, and T.J. Walsh Mycoses 53 2010 239 245
36. National Committee for Clinical Laboratory Standards Approved standard Document M27-A2, Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts 2002 National Committee for Clinical Laboratory Standards Wayne, PA
37. A. Bhattacharya, L.C. Mishra, M. Sharma, S.K. Awasthi, and V.K. Bhasin Eur. J. Med. Chem. 44 2009 3388 3393
38. L.C. Mishra, A. Bhattacharya, and V.K. Bhasin Am. J. Trop. Med. Hyg. 76 2007 497 501
39. A. Bhattacharya, L.C. Mishra, and V.K. Bhasin Am. J. Trop. Med. Hyg. 78 2008 721 728
40. D. Hunziker, P.C. Wyss, P. Angehrn, A. Mueller, H.P. Marty, R. Halm, L. Kellenberger, V. Bitsch, G. Biringer, W. Arnold, A. Stämpfli, A. Schmitt-Hoffmannb, and D. Cousot Bioorg. Med. Chem. 12 2004 3503 3519
41. L. Huang, M. Terakawa, T. Zhiyentayev, Y.Y. Huang, Y. Sawayama, A. Jahnke, G.P. Tegos, T. Wharton, and M.R. Hamblin Nanomedicine: NBM 6 2010 442 452
42. M.M. Ramla, M.A. Omar, H. Tokuda, and H.I. Ei-Diwani Bioorg. Med. Chem. 15 2007 6489 6496
43. K.C.S. Achar, K.M. Hosamani, and H.R. Seetharamareddy Eur. J. Med. Chem. 45 2010 2043 2054
44. N. Özbek, H. KatIrcIoglu, N. Karacan, and T. Baykal Bioorg. Med. Chem. 15 2007 5105 5109
45. A.A. Kadi, N.R. El-Brollosy, O.A. Al-Deeb, E.E. Habib, T.M. Ibrahim, and A.A. El-Emam Eur. J. Med. Chem. 42 2007 235 242