Click approach to the discovery of 1,2,3-triazolylsalicylamides as potent Aurora kinase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 17, 2014, Pages 4855-4866

  Song, Doohee ^a   Park, Yunjeong ^a   Yoon, Jieun ^a   Aman, Waqar ^b   Hah, Jung Mi ^b   Ryu, Jae Sang ^a  

^a Ewha Womans University   (South Korea)

^b Hanyang University   (South Korea)

Author keywords

1,2,3 Triazole; Anticancer; Aurora kinase; Click chemistry; Library

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; 1,2,3 TRIAZOLYLSALICYLAMIDE DERIVATIVE; 2 HYDROXY 5 [4 (1 METHYL 1H IMIDAZOL 5 YL) 1H 1,2,3 TRIAZOL 1 YL] N [3 (TRIFLUOROMETHYL)PHENYL]BENZAMIDE; 2 HYDROXY 5 [4 (4 TOLYL) 1H 1,2,3 TRIAZOL 1 YL] N [3 (TRIFLUOROMETHYL)PHENYL]BENZAMIDE; 2 HYDROXY 5 [4 (M TOLYL) 1H 1,2,3 TRIAZOL 1 YL] N [3 (TRIFLUOROMETHYL)PHENYL]BENZAMIDE; 2 HYDROXY 5 [4 (PYRIDIN 2 YL) 1H 1,2,3 TRIAZOL 1 YL] N [3 (TRIFLUOROMETHYL)PHENYL]BENZAMIDE; 2 HYDROXY 5 [4 (PYRIDIN 3 YL) 1H 1,2,3 TRIAZOL 1 YL] N [3 (TRIFLUOROMETHYL)PHENYL]BENZAMIDE; 2 HYDROXY 5 [4 (THIOPHEN 3 YL) 1H 1,2,3 TRIAZOL 1 YL] N [3 (TRIFLUOROMETHYL)PHENYL]BENZAMIDE; 3 [4 (3,5 DIMETHOXYPHENYL) 1H 1,2,3 TRIAZOL 1 YL] N [3 (TRIFLUOROMETHYL)PHENYL]BENZAMIDE; 5 [4 (3 ACETAMIDOPHENYL) 1H 1,2,3 TRIAZOL 1 YL] 2 HYDROXY N [3 (TRIFLUOROMETHYL)PHENYL]BENZAMIDE; 5 [4 (3 CHLOROPHENYL) 1H 1,2,3 TRIAZOL 1 YL] 2 HYDROXY N [3 (TRIFLUOROMETHYL)PHENYL]BENZAMIDE; 5 [4 (3,5 DIFLUOROPHENYL) 1H 1,2,3 TRIAZOL 1 YL] 2 HYDROXY N [3 (TRIFLUOROMETHYL)PHENYL]BENZAMIDE; 5 [4 (3,5 DIMETHOXYPHENYL) 1H 1,2,3 TRIAZOL 1 YL] 2 HYDROXY N (3 METHOXYPHENYL)BENZAMIDE; 5 [4 (3,5 DIMETHOXYPHENYL) 1H 1,2,3 TRIAZOL 1 YL] 2 HYDROXY N (M TOLYL)BENZAMIDE; 5 [4 (3,5 DIMETHOXYPHENYL) 1H 1,2,3 TRIAZOL 1 YL] 2 HYDROXY N PHENYLBENZAMIDE; 5 [4 (3,5 DIMETHOXYPHENYL) 1H 1,2,3 TRIAZOL 1 YL] 2 HYDROXY N [2 (TRIFLUOROMETHYL)PHENYL]BENZAMIDE; 5 [4 (4 CYANOPHENYL) 1H 1,2,3 TRIAZOL 1 YL] 2 HYDROXY N [3 (TRIFLUOROMETHYL)PHENYL]BENZAMIDE; 5 [4 (4 FLUOROPHENYL) 1H 1,2,3 TRIAZOL 1 YL] 2 HYDROXY N [3 (TRIFLUOROMETHYL)PHENYL]BENZAMIDE; 5 [4 (5 CHLORO 2,4 DIMETHOXYPHENYL) 1H 1,2,3 TRIAZOL 1 YL] 2 HYDROXY N [3 (TRIFLUOROMETHYL)PHENYL]BENZAMIDE; 5 [4 [3,5 BIS(TRIFLUOROMETHYL)PHENYL] 1H 1,2,3 TRIAZOL 1 YL] 2 HYDROXY N [3 (TRIFLUOROMETHYL)PHENYL]BENZAMIDE; 5 [4 [4 (DIMETHYLAMINO)PHENYL] 1H 1,2,3 TRIAZOL 1 YL] 2 HYDROXY N [3 (TRIFLUOROMETHYL)PHENYL]BENZAMIDE; AURORA A KINASE; AURORA KINASE INHIBITOR; METHYL 3 [1 [4 HYDROXY 3 [[3 (TRIFLUOROMETHYL)PHENYL]CARBAMOYL]PHENYL] 1H 1,2,3 TRIAZOL 4 YL]BENZOATE; METHYL 3 [5 [4 (3,5 DIMETHOXYPHENYL) 1H 1,2,3 TRIAZOL 1 YL] 2 HYDROXYBENZAMIDO]BENZOATE; METHYL 4 [1 [4 HYDROXY 3 [[3 (TRIFLUOROMETHYL)PHENYL]CARBAMOYL]PHENYL] 1H 1,2,3 TRIAZOL 4 YL]BENZOATE; N (3 CHLOROPHENYL) 5 [4 (3,5 DIMETHOXYPHENYL) 1H 1,2,3 TRIAZOL 1 YL] 2 HYDROXYBENZAMIDE; SALICYLAMIDE DERIVATIVE; STAUROSPORINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; AURKA PROTEIN, HUMAN; AURORA B KINASE; METHYL 3-(5-(4-(3,5-DIMETHOXYPHENYL)-1H-1,2,3-TRIAZOL-1-YL)-2-HYDROXYBENZAMIDO)BENZOATE; PROTEIN KINASE INHIBITOR; TRIAZOLE DERIVATIVE;

ARTICLE; CLICK CHEMISTRY; CONTROLLED STUDY; CYCLOADDITION; DRUG DESIGN; DRUG SCREENING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HYDROGEN BOND; IC 50; MOLECULAR MODEL; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG DEVELOPMENT; HUMAN; METABOLISM; MOLECULAR DOCKING; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AURORA KINASE A; AURORA KINASE B; CLICK CHEMISTRY; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DISCOVERY; HUMANS; MOLECULAR DOCKING SIMULATION; MOLECULAR STRUCTURE; PROTEIN KINASE INHIBITORS; SALICYLAMIDES; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

EID: 84906935513     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.06.047     Document Type: Article

References (21)

1. M. Carmena, and W.C. Earnshaw Nat. Rev. Mol. Cell Biol. 4 2003 842
2. T. Marumoto, D. Zhang, and H. Saya Nat. Rev. Cancer 5 2005 42
3. N. Keen, and S. Taylor Nat. Rev. Cancer 4 2004 927
4. E.C.Y. Lee, A. Frolov, R. Li, G. Ayala, and N.M. Greenberg Cancer Res. 66 2006 4996
5. R.R. Adams, S.P. Wheatleya, A.M. Gouldsworthy, S.E. Kandels-Lewis, M. Carmena, C. Smythe, D.L. Gerloff, and W.C. Earnshaw Curr. Biol. 10 2000 1075
6. J.-Y. Hsu, Z.-W. Sun, X. Li, M. Reuben, K. Tatchell, D.K. Bishop, J.M. Grushcow, C.J. Brame, J.A. Caldwell, D.F. Hunt, R. Lin, M.M. Smith, and C.D. Allis Cell 102 2000 279
7. K. Sasai, H. Katayama, D.L. Stenoien, S. Fujii, R. Honda, M. Kimura, Y. Okano, M. Tatsuka, F. Suzuki, E.A. Nigg, W.C. Earnshaw, W.R. Brinkley, and S. Sen Cell Motil. Cytoskeleton 59 2004 249
8. R.D. Carvajal, A. Tse, and G.K. Schwartz Clin. Cancer Res. 12 2006 6869
9. O. Gautschi, J. Heighway, P.C. Mack, P.R. Purnell, P.N. Lara Jr., and D.R. Gandara Clin. Cancer Res. 14 2008 1639
10. F. Girdler, K.E. Gascoigne, P.A. Eyers, S. Hartmuth, C. Crafter, K.M. Foote, N.J. Keen, and S.S. Taylor J. Cell Sci. 119 2006 3664
11. E.A. Harrington, D. Bebbington, J. Moore, R.K. Rasmussen, A.O. Ajose-Adeogun, T. Nakayama, J.A. Graham, C. Demur, T. Hercend, A. Diu-Hercend, M. Su, J.M. Golec, and K.M. Miller Nat. Med. 10 2004 262
12. J.D. Oslob, M.J. Romanowski, D.A. Allen, S. Baskaran, M. Bui, R.A. Elling, W.M. Flanagan, A.D. Fung, E.J. Hanan, S. Harris, S.A. Heumann, U. Hoch, J.W. Jacobs, J. Lam, C.E. Lawrence, R.S. McDowell, M.A. Nannini, W. Shen, J.A. Silverman, M.M. Sopko, B.T. Tangonan, J. Teague, J.C. Yoburn, C.H. Yu, M. Zhong, K.M. Zimmerman, T. O'Brien, and W. Lew Bioorg. Med. Chem. Lett. 18 2008 4880
13. D.A. Sloane, M.Z. Trikic, M.L. Chu, M.B. Lamers, C.S. Mason, I. Mueller, W.J. Savory, D.H. Williams, and P.A. Eyers ACS Chem. Biol. 5 2010 563
14. T. Shimomura, S. Hasako, Y. Nakatsuru, T. Mita, K. Ichikawa, T. Kodera, T. Sakai, T. Nambu, M. Miyamoto, I. Takahashi, S. Miki, N. Kawanishi, M. Ohkubo, H. Kotani, and Y. Iwasawa Mol. Cancer Ther. 9 2010 157
15. A.A. Mortlock, K.M. Foote, N.M. Heron, F.H. Jung, G. Pasquet, J.J. Lohmann, N. Warin, F. Renaud, C. De Savi, N.J. Roberts, T. Johnson, C.B. Dousson, G.B. Hill, D. Perkins, G. Hatter, R.W. Wilkinson, S.R. Wedge, S.P. Heaton, R. Odedra, N.J. Keen, C. Crafter, E. Brown, K. Thompson, S. Brightwell, L. Khatri, M.C. Brady, S. Kearney, D. McKillop, S. Rhead, T. Parry, and S. Green J. Med. Chem. 50 2007 2213
16. N.D. Adams, J.L. Adams, J.L. Burgess, A.M. Chaudhari, R.A. Copeland, C.A. Donatelli, D.H. Drewry, K.E. Fisher, T. Hamajima, M.A. Hardwicke, W.F. Huffman, K.K. Koretke-Brown, Z.V. Lai, O.B. McDonald, H. Nakamura, K.A. Newlander, C.A. Oleykowski, C.A. Parrish, D.R. Patrick, R. Plant, M.A. Sarpong, K. Sasaki, S.J. Schmidt, D.J. Silva, D. Sutton, J. Tang, C.S. Thompson, P.J. Tummino, J.C. Wang, H. Xiang, J. Yang, and D. Dhanak J. Med. Chem. 53 2010 3973
17. J. Yoon, and J.-S. Ryu Bioorg. Med. Chem. Lett. 20 2010 3930
18. T. Onoda, H. Iinuma, Y. Sasaki, M. Hamada, K. Isshiki, H. Naganawa, T. Takeuchi, K. Tatsuta, and K. Umezawa J. Nat. Prod. 52 1989 1252
19. Reaction Biology Corporation Web Site, www.reactionbiology.com.
20. S.G. Agalave, S.R. Maujan, and V.S. Pore Chem. Asian J. 6 2011 2696
21. D.K. Dalvie, A.S. Kalgutkar, S.C. Khojasteh-Bakht, R.S. Obach, and J.P. O'Donnell Chem. Res. Toxicol. 15 2002 269