Design, synthesis and biological evaluation of novel anti-cytokine 1,2,4-triazine derivatives

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 21, 2013, Pages 6708-6717

  Khoshneviszadeh, Mehdi ^a,b   Ghahremani, Mohammad H ^c   Foroumadi, Alireza ^a,d   Miri, Ramin ^b   Firuzi, Omidreza ^b   Madadkar Sobhani, Armin ^e   Edraki, Najmeh ^a,b   Parsa, Maliheh ^c   Shafiee, Abbas ^a  

^a TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b SHIRAZ UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^d KERMAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^e UNIVERSITY OF TEHRAN   (Iran)

Author keywords

Anti inflammatory activity; IL 1 ; MAPK 1,2,4 Triazine; TNF p38

Indexed keywords

1,2,4 TRIAZINE DERIVATIVE; 3 (2 BENZYLIDENEHYDRAZINYL) 5,6 BIS(4 METHOXYPHENYL)1,2,4 TRIAZINE; 3 [2 (1,2 DIHYDROXYBENZYLIDENE)HYDRAZINYL] 5,6 BIS(4 METHOXYPHENYL)1,2,4 TRIAZINE; 3 [2 (1,3 DIHYDROXYBENZYLIDENE)HYDRAZINYL] 5,6 BIS(4 METHOXYPHENYL)1,2,4 TRIAZINE; 3 [2 (2,3 DIMETHOXYBENZYLIDENE)HYDRAZINYL] 5,6 BIS(4 METHOXYPHENYL)1,2,4 TRIAZINE; 3 [2 (2,4 DICHLOROBENZYLIDENE)HYDRAZINYL] 5,6 BIS(4 METHOXYPHENYL)1,2,4 TRIAZINE; 3 [2 (3,4 DIMETHOXYBENZYLIDENE)HYDRAZINYL] 5,6 BIS(4 METHOXYPHENYL)1,2,4 TRIAZINE; 3 [2 (4 FLUOROBENZYLIDENE)HYDRAZINYL] 5,6 BIS(4 METHOXYPHENYL)1,2,4 TRIAZINE; 3 [2 (4 HYDROXY 3 METHOXYBENZYLIDENE)HYDRAZINYL] 5,6 BIS(4 METHOXYPHENYL)1,2,4 TRIAZINE; 3 [2 (4 METHOXYBENZYLIDENE)HYDRAZINYL] 5,6 BIS(4 METHOXYPHENYL)1,2,4 TRIAZINE; 3 [2 (BENZO[D][1,3]DIOXOL 5 YLMETHYLENE)HYDRAZINYL] 5,6 BIS(4 METHOXYPHENYL)1,2,4 TRIAZINE; 3 [2 (FURAN 2 YLMETHYLENE)HYDRAZINYL] 5,6 BIS(4 METHOXYPHENYL)1,2,4 TRIAZINE; 5,6 BIS(4 METHOXYPHENYL) 3 [2 (4 NITROBENZYLIDENE)HYDRAZINYL]1,2,4 TRIAZINE; 5,6 BIS(4 METHOXYPHENYL) 3 [2 (PYRIDIN 4 YLMETHYLENE)HYDRAZINYL]1,2,4 TRIAZINE; 5,6 BIS(4 METHOXYPHENYL) 3 [2 (THIOPHEN 2 YLMETHYLENE)HYDRAZINYL]1,2,4 TRIAZINE; 5,6 BIS(4 METHOXYPHENYL) 3 [2 [(1H INDOL 3 YL)METHYLENE]HYDRAZINYL]1,2,4 TRIAZINE; CARRAGEENAN; INDOMETACIN; INTERLEUKIN 1BETA; MITOGEN ACTIVATED PROTEIN KINASE P38; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; BINDING SITE; CELL STRAIN MCF 7; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; INHIBITION KINETICS; MOLECULAR DOCKING; NONHUMAN; PAW EDEMA; PERIPHERAL BLOOD MONONUCLEAR CELL; RAT; SIGNAL TRANSDUCTION; WESTERN BLOTTING;

RATTUS;

1,2,4-TRIAZINE; ANTI-INFLAMMATORY ACTIVITY; IL-1Β; P38 MAPK; TNF-Α;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BINDING SITES; CARRAGEENAN; CELL SURVIVAL; CELLS, CULTURED; DRUG DESIGN; EDEMA; HUMANS; HYDRAZONES; INTERLEUKIN-1BETA; LEUKOCYTES, MONONUCLEAR; MCF-7 CELLS; MOLECULAR DOCKING SIMULATION; P38 MITOGEN-ACTIVATED PROTEIN KINASES; PROTEIN STRUCTURE, TERTIARY; RATS; SIGNAL TRANSDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZINES; TUMOR NECROSIS FACTOR-ALPHA;

EID: 84885172184     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.08.009     Document Type: Article

References (47)

1. A.A. Abdel-Aziz, K.E. ElTahir, and Y.A. Asiri Eur. J. Med. Chem. 46 2011 1648
2. M.R. Shaaban, T.S. Saleh, A.S. Mayhoub, A. Mansour, and A.M. Farag Bioorg. Med. Chem. 16 2008 6344
3. A. Uzgoren-Baran, B.C. Tel, D. Sarigol, E.I. Ozturk, I. Kazkayasi, G. Okay, M. Ertan, and B. Tozkoparan Eur. J. Med. Chem. 57 2012 398
4. R.B. Lacerda, C.K. de Lima, L.L. da Silva, N.C. Romeiro, A.L. Miranda, E.J. Barreiro, and C.A. Fraga Bioorg. Med. Chem. 17 2009 74
5. D. Williams, and T. Lemke Foye's Princ. Med. Chem. 2002 751
6. J. Bolos Mini-Rev. Med. Chem. 5 2005 857
7. M. Feldmann, and R.N. Maini Rheumatology (Oxford) 38 1999 3
8. S. Kuiper, L.A. Joosten, A.M. Bendele, C.K. Edwards 3rd, O.J. Arntz, M.M. Helsen, F.A. Van de Loo, and W.B. Van den Berg Cytokine 10 1998 690
9. D.M. Goldstein, and T. Gabriel Curr. Top. Med. Chem. 5 2005 1017
10. S.L. Colletti, J.L. Frie, E.C. Dixon, S.B. Singh, B.K. Choi, G. Scapin, C.E. Fitzgerald, S. Kumar, E.A. Nichols, S.J. O'Keefe, E.A. O'Neill, G. Porter, K. Samuel, D.M. Schmatz, C.D. Schwartz, W.L. Shoop, C.M. Thompson, J.E. Thompson, R. Wang, A. Woods, D.M. Zaller, and J.B. Doherty J. Med. Chem. 46 2003 349
11. D.A. Cogan, R. Aungst, E.C. Breinlinger, T. Fadra, D.R. Goldberg, M.H. Hao, R. Kroe, N. Moss, C. Pargellis, K.C. Qian, and A.D. Swinamer Bioorg. Med. Chem. Lett. 18 2008 3251
12. R. Soliva, J.L. Gelpi, C. Almansa, M. Virgili, and M. Orozco J. Med. Chem. 50 2007 283
13. R.J. Mayer, and J.F. Callahan Drug Discovery Today 3 2006 49
14. M. Kikuchi, L. Tenneti, and S.A. Lipton J. Neurosci. 20 2000 5037
15. S.A. Laufer, D.R. Hauser, D.M. Domeyer, K. Kinkel, and A.J. Liedtke J. Med. Chem. 51 2008 4122
16. S.A. Laufer, G.M. Ahrens, S.C. Karcher, J.S. Hering, and R. Niess J. Med. Chem. 49 2006 7912
17. N.C. Romeiro, M.G. Albuquerque, R.B. de Alencastro, M. Ravi, and A.J. Hopfinger J. Comput. Aided Mol. Des. 19 2005 385
18. G. Wagner, and S. Laufer Med. Res. Rev. 26 2005 1
19. A. Rineh, N. Mahmoodi, M. Abdollahi, A. Foroumadi, M. Sorkhi, and A. Shafiee Arch. Pharm. 340 2007 409
20. A. Almasirad, M. Tajik, D. Bakhtiari, A. Shafiee, M. Abdollahi, M. Zamani, R. Khorasani, and H. Esmaily J. Pharm. Pharm. Sci. 8 2005 419
21. L. Navidpour, H. Shafaroodi, K. Abdi, M. Amini, M.H. Ghahremani, A.R. Dehpour, and A. Shafiee Bioorg. Med. Chem. 14 2006 2507
22. A. Moradi, L. Navidpour, M. Amini, H. Sadeghian, H. Shadnia, O. Firouzi, R. Miri, S.E.S. Ebrahimi, M. Abdollahi, and M.H. Zahmatkesh Arch. Pharm. 343 2010 509
23. O. Bekircan, M. Kuxuk, B. Kahveci, and S. Kolayli Arch. Pharm. 338 2005 365
24. W.A. Creasey, M.E. Fink, R.E. Handschumacher, and P. Calabresi Cancer Res. 23 1963 444
25. T.R. Walters, R.J. Aur, K. Hernandez, T. Vietti, and D. Pinkel Cancer 29 1972 1057
26. Z. Brzozowski, and F. Saczewski Eur. J. Med. Chem. 37 2002 709
27. A. Iwashita, T. Maemoto, H. Nakada, I. Shima, N. Matsuoka, and H. Hisajima J. Pharm. Exp. Ther. 307 2003 961
28. W. Kim, Y. Kim, J. Min, D.J. Kim, Y.T. Chang, and M.H. Hecht ACS Chem. Biol. 1 2006 461
29. J.C. Hunt, E. Briggs, E.D. Clarke, and W.G. Whittingham Bioorg. Med. Chem. Lett. 17 2007 5222
30. R.J. Hill, K. Dabbagh, D. Phippard, C. Li, R.T. Suttmann, M. Welch, E. Papp, K.W. Song, K. Chang, and D. Leaffer J. Pharm. Exp. Ther. 327 2008 610
31. T. Matsuda, T. Aoki, T. Ohgiya, T. Koshi, M. Ohkuchi, and H. Shigyo Bioorg. Med. Chem. Lett. 11 2001 2369
32. T. Matsuda, T. Aoki, T. Koshi, M. Ohkuchi, and H. Shigyo Bioorg. Med. Chem. Lett. 11 2001 2373
33. A. Almasirad, R. Hosseini, H. Jalalizadeh, Z. Rahimi-Moghaddam, N. Abaeian, M. Janafrooz, M. Abbaspour, V. Ziaee, A. Dalvandi, and A. Shafiee Biol. Pharm. Bull. 29 2006 1180
34. Mantlo, N. B.; Hwang, C.-K.; Spohr, U. D.; China Patent 98813653, 2001.
35. J. Hynes Jr., and K. Leftheri Curr. Top. Med. Chem. 5 2005 967
36. S. Bag, V.V. Vaze, and M.S. Degani J. Chem. Res. 2006 2006 267
37. H. Irannejad, M. Amini, F. Khodagholi, N. Ansari, S.K. Tusi, M. Sharifzadeh, and A. Shafiee Bioorg. Med. Chem. 18 2010 4224
38. S.V. Saxena, M. Verma, A.K. Saxena, and K. Shanker Arzneim.-Forsch./Drug Res. 44 1994 766
39. J. Thomas, C.E. Berkoff, W.B. Flagg, J.J. Gallo, R.F. Haff, and C.A. Pinto J. Med. Chem. 18 1975 245
40. E.R. Ottosen, M.D. Sørensen, F. Björkling, T. Skak-Nielsen, M.S. Fjording, H. Aaes, and L. Binderup J. Med. Chem. 46 2003 5651
41. C. Zhao, J. Yang, Y. Wang, D. Liang, X. Yang, X. Li, J. Wu, X. Wu, S. Yang, and G. Liang Bioorg. Med. Chem. 18 2010 2388
42. F. Mir Mohammadrezaei, H. Mohseni kouchesfehani, H. Montazeri, M. Gharghabi, S.N. Ostad, and M.H. Ghahremani Cell. Signal. 25 2013 126
43. G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, and A.J. Olson J. Comput. Chem. 19 1998 1639
44. Lacefield, W. B.; US 3979516, 1976.
45. C.A. Winter, E.A. Risley, and G.W. Nuss Proc. Soc. Exp. Biol. Med. 111 1962 544
46. M. Shekarchi, L. Navidpour, A. Rajabi Khorami, A. Partoazar, H. Shafaroodi, N. Rahmanipour, A. Shafiee, and M. Shekarchi Iran. J. Pharm. Res. 10 2011 369
47. N. Edraki, O. Firuzi, A. Foroumadi, R. Miri, A. Madadkar-Sobhani, M. Khoshneviszadeh, and A. Shafiee Bioorg. Med. Chem. 21 2013 2396