Synthesis of benzimidazole derivatives as potent β-glucuronidase inhibitors

Bioorganic Chemistry

Volumn 61, Issue , 2015, Pages 36-44

  Taha, Muhammad ^a   Ismail, Nor Hadiani ^a   Imran, Syahrul ^a   Selvaraj, Manikandan ^a   Rashwan, Hesham ^a   Farhanah, Fatin Ummi ^a   Rahim, Fazal ^b   Kesavanarayanan, Krishnan Selvarajan ^c   Ali, Muhammad ^d  

^a UNIVERSITI TEKNOLOGI MARA   (Malaysia)

^b HAZARA UNIVERSITY   (Pakistan)

^c Pharmacology and Toxicology Research Laboratory Faculty of Pharmacy University Technology MARA (UiTM)   (Malaysia)

^d Faculty of Pharmacy Universiti Teknologi MARA ^*  (Pakistan)

Author keywords

Benzimidazole; Docking studies; Synthesis; Glucuronidase

Indexed keywords

2 (4,6 DICHLORO 1H BENZO[D]IMIDAZOL 2 YL) 4 METHOXYPHENOL; 2 (4,6 DICHLORO 1H BENZO[D]IMIDAZOL 2 YL) 5 METHOXYPHENOL; 2 (4,6 DICHLORO 1H BENZO[D]IMIDAZOL 2 YL)BENZENE 1,4 DIOL; 2 (4,6 DICHLORO 1H BENZO[D]IMIDAZOL 2 YL)PHENOL; 3 (4,6 DICHLORO 1H BENZO[D]IMIDAZOL 2 YL)BENZENE 1,2 DIOL; 3 (4,6 DICHLORO 1H BENZO[D]IMIDAZOL 2 YL)PHENOL; 4 (4,6 DICHLORO 1H BENZO[D]IMIDAZOL 2 YL)BENZENE 1,2 DIOL; 4 (4,6 DICHLORO 1H BENZO[D]IMIDAZOL 2 YL)BENZENE 1,3 DIOL; 4 (4,6 DICHLORO 1H BENZO[D]IMIDAZOL 2 YL)PHENOL; 4,6 DICHLORO 2 (2 FLUOROPHENYL) 1H BENZO[D]IMIDAZOLE; 4,6 DICHLORO 2 (2,6 DIMETHOXYPHENYL) 1H BENZO[D]IMIDAZOLE; 4,6 DICHLORO 2 (3 CHLOROPHENYL) 1H BENZO[D]IMIDAZOLE; 4,6 DICHLORO 2 (3 FLUOROPHENYL) 1H BENZO[D]IMIDAZOLE; 4,6 DICHLORO 2 (3 METHOXYPHENYL) 1H BENZO[D]IMIDAZOLE; 4,6 DICHLORO 2 (3,4 DIMETHOXYPHENYL) 1H BENZO[D]IMIDAZOLE; 4,6 DICHLORO 2 (4 CHLOROPHENYL) 1H BENZO[D]IMIDAZOLE; 4,6 DICHLORO 2 (4 FLUOROPHENYL) 1H BENZO[D]IMIDAZOLE; 4,6 DICHLORO 2 (4 NITROPHENYL) 1H BENZO[D]IMIDAZOLE; 4,6 DICHLORO 2 (PYRIDIN 2 YL) 1H BENZO[D]IMIDAZOLE; 4,6 DICHLORO 2 (PYRIDIN 3 YL) 1H BENZO[D]IMIDAZOLE; 4,6 DICHLORO 2 (PYRIDIN 4 YL) 1H BENZO[D]IMIDAZOLE; 4,6 DICHLORO 2 3 TOLYL 1H BENZO[D]IMIDAZOLE; 4,6 DICHLORO 2 4 TOLYL 1H BENZO[D]IMIDAZOLE; 4,6 DICHLORO 2 O TOLYL 1H BENZO[D]IMIDAZOLE; 5 (4,6 DICHLORO 1H BENZO[D]IMIDAZOL 2 YL) 2 METHOXYPHENOL; BENZIMIDAZOLE DERIVATIVE; BETA GLUCURONIDASE; GLYCOSIDASE INHIBITOR; UNCLASSIFIED DRUG; BETA-GLUCURONIDASE INHIBITOR; GLYCOPROTEIN; PROTEIN BINDING;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IC50; MOLECULAR DOCKING; MOLECULAR MODEL; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; ANTAGONISTS AND INHIBITORS; BINDING SITE; CHEMISTRY; HUMAN; METABOLISM; PROTEIN TERTIARY STRUCTURE; SYNTHESIS;

BENZIMIDAZOLES; BINDING SITES; GLUCURONIDASE; GLYCOPROTEINS; HUMANS; MOLECULAR DOCKING SIMULATION; PROTEIN BINDING; PROTEIN STRUCTURE, TERTIARY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84930958744     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2015.05.010     Document Type: Article

References (56)

1. H.W. Fishman, β-Glucuronidase, in: H.U. (Ed.), Academic Press, New York, USA, 1983, pp. 929.
2. K.M. Khan, N. Ambreen, M. Taha, and S.A. Halim J. Comput. Aided Mol. Des. 28 2014 577
3. C. Kunert-Keil, C.A. Ritter, H.K. Kroemer, and B. Sperker Deconjugating enzymes: sulphatases and glucuronidases C. Ioannides, Enzyme Systems that Metabolise Drugs and Other Xenobiotics vol. 2 2002 John Wiley & Sons Michigan, USA 521 (Chapter 15)
4. H.C. Gonick, H.J. Kramer, and A.E. Schapiro Arch. Intern. Med. 132 1973 63
5. W.L. Dibb, and K.L. Bottolfsen Acta. Path. Micro. IM. B. 9 1984 261
6. J.L. Perez, C.I. Berrocal, and L. Berrocal J. Appl. Bacteriol. 6 1986 541
7. G. Jadot, H. Bussiere, E. Mesdjian, M. Valli, and J. Roger Therapie 45 1989 151
8. D. Haidukewych, E. Rodin, and S. Schmaltz Ther. Drug Mon. 6 1984 15
9. R. Pantscheva-Haschen, R. Schulze, J. Haerting, B. Langkopf, and Z. Med Lab. Diagn. 29 1988 179
10. R.F. Dyck, C.J. Cardella, and M.A. Sacks Clin. Chim. Acta 91 1979 111
11. K. Paigen, J. Peterson, and B. Paigen Cancer Res. 44 1984 3620
12. E. Boyland, J.E. Gasson, and D.C. Williams Br. J. Cancer 11 1957 120
13. L. Moro, B.D. Bernard, and F. Gonano Clin. Chim. Acta 65 1975 371
14. K. Bramwell, Y. Ma, J. Weis, C. Teuscher, J. Zachary, and J. Weis J. Immunol. 190 2013 131
15. H. Ohta, M. Ono, C. Sekiya, and M. Namiki Clin. Chim. Acta 208 1992 9
16. J. George Biochem. Cell Biol. 86 2008 235
17. D.H. Kim, and Y.H. Jin Arch. Pharm. Res. 24 2001 564
18. B.R. Goldin, and S.L. Gorbach J. Natl. Cancer Inst. 57 1976 371
19. M. Wakabayyashi W.H. Fishman, Metabolic Conjugation and Metabolic Hydrolysis 1970 Academic Press New York 519
20. Z.M. Nofal, E.A. Soliman, S.S. Abdelkarim, M.I. Elzahar, A.M. Srour, S.H. Sethumadhavan, and T.J. Maher Acta Pol. Pharm. 68 2011 519
21. R. Walia, H. Md, S.F. Naaz, K. Iqbal, and H.S. Lamba Int. J. Res. Pharm. Chem. 1 2011 565
22. E.S.A. Ibrahim, A.M.M.E. Omar, M.E. Mohsen, and M.A. Khalil J. Pharma. Sci. 69 1980 1348
23. M. Taha, N.H. Ismail, W. Jamil, H. Rashwan, S.M. Kashif, A.A. Sain, M.I. Adenan, E.H. Anouar, M. Ali, F. Rahim, and K.M. Khan Eur. J. Med. Chem. 84 2014 731
24. X.J. Wang, M.Y. Xi, J.H. Fu, F.R. Zhang, G.F. Cheng, D.L. Yin, and Q.D. You Chem. Lett. 23 2012 707
25. Z.S. Saify, A. Kamil, S. Akhtar, M. Taha, A. Khan, K.M. Khan, S. Jahan, F. Rahim, S. Perveen, and M.I. Choudhary Med. Chem. Res. 23 2014 4447
26. G. Chen, Z. Liu, Y. Zhang, X. Shan, L. Jiang, Y. Zhao, G. Liang, and A.C.S. Med Chem. Lett. 4 2012 69
27. E.S. Lazer, M.R. Matteo, and G.J. Possanza J. Med. Chem. 30 1987 726
28. E.I. Elnima, M.U. Zubair, and A.A. Al-Badr Antimicrob. Agents Chemother. 19 1981 29
29. V. Křížová-Forstová, J. Lamka, V. Cvilink, V. Hanušová, and L. Skálová Res. Vet. Sci. 91 2011 333
30. T. Iwahi, H. Satoh, M. Nakao, T. Iwasaki, T. Yamazaki, K. Kubo, and A. Imada Antimicrob. Agents Chemother. 35 1991 490
31. R.K. Ujjinamatada, A. Baier, P. Borowski, and R.S. Hosmane Bioorg. Med. Chem. Lett. 17 2007 2285
32. K.M. Khan, M. Khan, M. Saleem, M. Taha, S. Perveen, and M.I. Choudhary J. Pak. Chem. Soc. 35 2013 901
33. K.M. Khan Bioorg. Med. Chem. 20 2012 1521
34. J.R. Kumar, L. Jawahar, and D.P. Pathak J. Chem. 3 2006 278
35. H.L. Kuo, J.C. Lien, C.H. Chung, C.H. Chang, S.C. Lo, I.C. Tsai, and T.F. Huang Naunyn-Schmiedeberg's Arch. Pharmacol. 381 2010 495
36. K.M. Khan, F. Rahim, S.A. Halim, M. Taha, M. Khan, S. Perveen, Z. Haq, M.A. Mesaik, and M.I. Choudhary Bioorg. Med. Chem. 19 2011 4286
37. K.M. Khan, F. Rahim, A. Wadood, M. Taha, M. Khan, S. Naureen, and M.I. Choudhary Bioorg. Med. Chem. Lett. 24 2014 1825
38. K.M. Khan, F. Naz, M. Taha, A. Khan, S. Perveen, M.I. Choudhary, and W. Voelter Eur. J. Med. Chem. 74 2014 314
39. K.M. Khan, F. Rahim, A. Wadood, N. Kosar, M. Taha, S. Lalani, A. Khan, M.I. Fakhri, M. Junaid, W. Rehman, M. Khan, S. Perveen, M. Sajid, and M.I. Choudhary Eur. J. Med. Chem. 81 2014 245
40. F. Rahim, K. Ullah, H. Ullah, A. Wadood, M. Taha, A.U. Rehman, M. Ashraf, A. Shaukat, W. Rehman, S. Hussain, and K.M. Khan Bioorg. Chem. 58 2015 81
41. M. Taha, N.H. Ismail, S. Lalani, M.Q. Fatmi, Atia-tul-Wahab, S. Siddiqui, K.M. Khan, S. Imran, and M.I. Choudhary Eur. J. Med. Chem. 92 2015 387
42. S. Imran, M. Taha, N.H. Ismail, K.M. Khan, F. Naz, M. Hussain, and S. Tauseef Molecules 19 2014 11722
43. M. Taha, N.H. Ismail, S. Imran, and K.M. Khan Molbank 2014 M826
44. K.M. Khan, M. Ali, M. Taha, S. Perveen, M.I. Choudhary, and W. Voelter Lett. Org. Chem. 5 2008 432
45. K.M. Khan, M. Taha, M. Ali, and S. Perveen Lett. Org. Chem. 6 2009 319
46. S. Jain, W.B. Drendel, Z.W. Chen, F.S. Mathews, W.S. Sly, and J.H. Grubb Nat. Struct. Biol. 3 1996 375
47. E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, and E.C. Meng J. Comput. Chem. 13 2004 1605
48. MarvinSketch V 5.2.6, ChemAxon Ltd, copyright, 1998-2009.
49. G. Jones, P. Willett, R.C. Glen, A.R. Leach, and R.J. Taylor Mol. Biol. 267 1997 727
50. G.T. Costakes eJournal 1 2006 1 4
51. PyMOL Molecular Graphics System, Schrçdinger L, NY, USA, 2010.
52. O. Trott, and A.J.J. Olson Comput. Chem. 31 2010 455
53. G.M. Morris, R. Huey, W. Lindstrom, M.F. Sanner, R.K. Belew, D.S. Goodsell, and A.J.J. Olson Comput. Chem. 30 2009 2785
54. M.F.J. Sanner Mol. Graphics Modell. 17 1999 57
55. W. Jamil, S. Perveen, S.A.A. Shah, M. Taha, N.H. Ismail, S. Perveen, N. Ambreen, K.M. Khan, and M.I. Choudhary Molecules 19 2014 8788
56. N.K.N.Z. Abdullah, M. Taha, N. Ahmat, A. Wadood, N.H. Ismail, F. Rahim, M. Ali, N. Abdullah, K.M. Khan, Bioorg. Med. Chem. (2015), http://dx.doi.org/10.1016/j.bmc.2015.04.081 (in press).