Synthesis, biological evaluation and molecular docking studies of 1,3,4-oxadiazole derivatives as potential immunosuppressive agents

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 10, 2012, Pages 3359-3367

  Zhang, Zhi Ming ^a   Zhang, Xue Wei ^a   Zhao, Zong Zheng ^a   Yan, Ru ^a   Xu, Rui ^a   Gong, Hai Bin ^b   Zhu, Hai Liang ^a  

^a NANJING UNIVERSITY   (China)

^b XUZHOU CENTRAL HOSPITAL   (China)

Author keywords

1,3,4 Oxadiazole derivatives; Immunosuppressive activities; Molecular docking; PI3K inhibitor

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; 2 [5 (BENZYLTHIO) 1,3,4 OXADIAZOL 2 YL] 5 METHOXYPHENOL; 2 [5 (BENZYLTHIO) 1,3,4 OXADIAZOL 2 YL] 5 METHYLPHENOL; 2 [5 [(2 CHLOROBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL] 5 METHOXYPHENOL; 2 [5 [(2 CHLOROBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL] 5 METHYLPHENOL; 2 [5 [(2 FLUOROBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL] 5 METHOXYPHENOL; 2 [5 [(2 FLUOROBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL] 5 METHYLPHENOL; 2 [5 [(3 CHLOROBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL] 5 METHOXYPHENOL; 2 [5 [(3 CHLOROBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL] 5 METHYLPHENOL; 2 [5 [(3 METHOXYBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL] 5 METHYLPHENOL; 2 [5 [(3 METHOXYBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL]PHENOL; 2 [5 [(4 CHLOROBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL] 5 METHOXYPHENOL; 2 [5 [(4 CHLOROBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL] 5 METHYLPHENOL; 2 [5 [(4 FLUOROBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL] 5 METHOXYPHENOL; 2 [5 [(4 FLUOROBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL] 5 METHYLPHENOL; 2 [5 [(4 METHOXYBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL] 5 METHYLPHENOL; 2 MORPHOLINO 8 PHENYLCHROMONE; 4 METHOXYSALICYLIC ACID; 5 METHOXY 2 [5 [(2 NITROBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL]PHENOL; 5 METHOXY 2 [5 [(3 METHYLBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL]PHENOL; 5 METHOXY 2 [5 [(3 NITROBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL]PHENOL; 5 METHOXY 2 [5 [(4 METHYLBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL]PHENOL; 5 METHOXY 2 [5 [(4 NITROBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL]PHENOL; 5 METHYL 2 [5 [(3 METHYLBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL] 5 METHYLPHENOL; 5 METHYL 2 [5 [(4 METHYLBENZYL)THIO] 1,3,4 OXADIAZOL 2 YL] 5 METHYLPHENOL; CYCLOSPORIN A; IMMUNOSUPPRESSIVE AGENT; PHOSPHATIDYLINOSITOL 3 KINASE GAMMA; SALICYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; APOPTOSIS; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVE SITE; FLOW CYTOMETRY; HYDROGEN BOND; IC 50; LYMPH NODE CELL; LYMPHOCYTE PROLIFERATION; MOLECULAR DOCKING; NONHUMAN; T LYMPHOCYTE;

ANIMALS; APOPTOSIS; CATALYTIC DOMAIN; CELL PROLIFERATION; FLOW CYTOMETRY; IMMUNOSUPPRESSIVE AGENTS; INHIBITORY CONCENTRATION 50; MICE; MICE, INBRED BALB C; MODELS, MOLECULAR; OXADIAZOLES; T-LYMPHOCYTES;

EID: 84860427360     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.03.064     Document Type: Article

References (40)

1. H. Hackstein, and A.W. Thomson Nat. Rev. Immunol. 4 2004 24
2. B.D. Kahan Nat. Rev. Immunol. 3 2003 831
3. S. De Jonghe, A. Marchand, L.J. Gao, A. Calleja, E. Cuveliers, I. Sienaert, J. Herman, G. Clydesdale, H. Sefrioui, Y. Lin, W. Pfleiderer, M. Waer, and P. Herdewijn Bioorg. Med. Chem. Lett. 21 2011 145
4. Y.R. Wang Chin. J. New Drugs. 11 2002 512
5. X.L. Wang, F. Tang, and H.M. Li J. Chin. Phys. 4 2002 1291
6. D. Sheikh-Hamad, V. Nadkarni, Y.J. Choi, L.D. Truong, C. Wideman, R. Hodjati, and K.H. Gabbay J. Am. Soc. Nephrol. 12 2001 2732
7. L.W. Miller Am. J. Tranplant. 2 2002 807
8. J.M. Smith, T.L. Nemeth, and R.A. McDonald Pedratr. Clin. North Am. 50 2003 1283
9. L.C. Cantley Science 296 2002 1655
10. S.G. Ward, and P. Finan Curr. Opin. Pharmacol. 3 2003 426
11. J.A. Engelman, J. Luo, and L.C. Cantley Nat. Rev. Genet. 7 2006 606
12. C. Rommel, M. Camps, and H. Ji Nat. Rev. Immunol. 7 2007 191
13. R. Marone, V. Cmiljanovic, B. Giese, and M.P. Wymann Biochim. Biophys. Acta 1784 2008 159
14. A. Fougerat, S. Gayral, P. Gourdy, A. Schambourg, T. Rückle, M.K. Schwarz, C. Rommel, E. Hirsch, J.F. Arnal, J.P. Salles, B. Perret, M. Breton-Douillon, M.P. Wymann, and M. Laffargue Circulation 117 2008 1310
15. M. Camps, T. Rückle, H. Ji, V. Ardissone, F. Rintelen, J. Shaw, C. Ferrandi, C. Chabert, C. Gillieron, B. Françon, T. Martin, D. Gretener, D. Perrin, D. Leroy, P.A. Vitte, E. Hirsch, M.P. Wymann, R. Cirillo, M.K. Schwarz, and C. Rommel Nat. Med. 11 2005 936
16. T. Rückle, M.K. Schwarz, and C. Rommel Nat. Rev. Drug. Disc. 5 2006 903
17. C. Ferrandi, V. Ardissone, P. Ferro, T. Rückle, P. Zaratin, E. Ammannati, E. Hauben, C. Rommel, and R. Cirillo J. Pharmacol. Exp. Ther. 322 2007 923
18. S.J. Dolman, F. Gosselin, P.D. OShea, and I.W. Davies J. Org. Chem. 71 2006 9548
19. C.J. Chen, B.A. Song, S. Yang, G.F. Xu, P.S. Bhadury, L.H. Jin, D.Y. Hu, Q.Z. Li, F. Liu, W. Xue, P. Lu, and Z. Chen Bioorg. Med. Chem. 15 2007 3981
20. A. Zarghi, S.A. Tabatabai, M. Faizi, A. Ahadian, P. Navabi, V. Zanganeh, and A. Shafiee Bioorg. Med. Chem. Lett. 2005 1863 15
21. Y.P. Luo, and G.F. Yang Bioorg. Med. Chem. 15 2007 1716
22. M.T. Khan, M.I. Choudhary, K.M. Khan, M. Rani, and A.U. Rahman Bioorg. Med. Chem. 13 2005 3385
23. J.T. Palmer, B.L. Hirschbein, H. Cheung, J. McCarter, J.W. Janc, W.Z. Yu, and G. Wesolowski Bioorg. Med. Chem. Lett. 16 2006 2909
24. K. Manjunatha, B. Poojary, L.L. Prajwal, J. Fernandes, and N.S. Kumari Eur. J. Med. Chem. 45 2010 5225
25. H. Kumar, S.A. Javed, and S.A. Khan Eur. J. Med. Chem. 43 2008 2688
26. T. Chandra, N. Garg, S. Lata, and K.K. Saxena Eur. J. Med. Chem. 45 2010 1772
27. C.R.W. Guimaraes, D.L. Boger, and W.L. Jorgensen J. Am. Chem. Soc. 127 2005 17377
28. B. Frantz, and E.A. O'Neill Science 2017 1995 270
29. K.K. Wu Circulation 102 2000 2022
30. D.E. Marra, T. Simoncini, and J.K. Liao Circulation 102 2000 2124
31. R.H. Cao, Q. Chen, X.R. Hou, H.S. Chen, H.J. Guan, Y. Ma, W.L. Peng, and A.L. Xu Bioorg. Med. Chem. 12 2004 4613
32. L. Chen, M. Hainrichson, D. Bourdetsky, A. Mor, S. Yaron, and T. Baasov Bioorg. Med. Chem. 16 2008 8940
33. L. Racané, M. Kralj, L. Šuman, R. Stojkovic, T.V. Kulenovic, and K.Z. Grace Bioorg. Med. Chem. 1038 2010 18
34. V. Pomel, J. Klicic, D. Covini, D.D. Church, J.P. Shaw, K. Roulin, F. Burgat-Charvillon, D. Valognes, M. Camps, C. Chabert, C. Gillieron, B. Francon, D. Perrin, D. Leroy, D. Gretener, A. Nichols, P.A. Vitte, S. Carboni, C. Rommel, M.K. Schwarz, and T. Ruckle J. Med. Chem. 49 2006 3857
35. C.J. Vlahos, W.F. Matter, K.Y. Hui, and R.F. Brown J. Biol. Chem. 269 1994 5241
36. J.D. Kendall, G.W. Rewcastle, R. Frederick, C. Mawson, W.A. Denny, E.S. Marshall, B.C. Baguley, C. Chaussade, S.P. Jackson, and P.R. Shepherd Bioorg. Med. Chem. 15 2007 7677
37. C. Chaussade, G.W. Rewcastle, J.D. Kendall, W.A. Denny, K. Cho, L.M. Gronning, M.L. Chong, S.H. Anagnostou, S.P. Jackson, N. Daniele, and P.R. Shepherd Biochem. J. 404 2007 44
38. S.D. Knight, N.D. Adams, J.L. Burgess, A.M. Chaudhari, M.G. Darcy, C.A. Donatelli, J.I. Luengo, K.A. Newlander, C.A. Parrish, L.H. Ridgers, M.A. Sarpong, S.J. Schmidt, G.S. Van Aller, J.D. Carson, M.A. Diamond, P.A. Elkins, C.M. Gardiner, E. Garver, S.A. Gilbert, R.R. Gontarek, J.R. Jackson, K.L. Kershner, L. Luo, K. Raha, C.S. Sherk, C.-M. Sung, D. Sutton, P.J. Tummino, R.J. Wegrzyn, K.R. Auger, and D. Dhanak ACS Med. Chem. Lett. 1 2010 39
39. V. Pomel, J. Klicic, D. Covini, D.D. Church, J.P. Shaw, K. Roulin, F. Burgat-Charvillon, D. Valognes, M. Camps, C. Chabert, C. Gillieron, B. Francon, D. Perrin, D. Leroy, D. Gretener, A. Nichols, P.A. Vitte, S. Carboni, C. Rommel, M.K. Schwarz, and T. Ruckle J. Med. Chem. 49 2006 3857
40. C. Chaussade, G.W. Rewcastle, J.D. Kendall, W.A. Denny, K. Cho, L.M. Gronning, M.L. Chong, S.H. Anagnostou, S.P. Jackson, N. Daniele, and P.R. Shepherd Biochem. J. 404 2007 449