Design, synthesis and SAR exploration of tri-substituted 1,2,4-triazoles as inhibitors of the annexin A2-S100A10 protein interaction

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 19, 2014, Pages 5378-5391

  Reddy, Tummala R K ^a,b   Li, Chan ^a   Guo, Xiaoxia ^a   Fischer, Peter M ^a   Dekker, Lodewijk V ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b UNIVERSITY OF HERTFORDSHIRE   (United Kingdom)

Author keywords

Annexins; Docking; S100 proteins; Triazole

Indexed keywords

1,2,4 TRIAZOLE DERIVATIVE; 2 [4 (4 CHLOROPHENYL) 5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4H [1,2,4]TRIAZOL 3 YLSULFANYL] N (3,4 DIMETHYLPHENYL)ACETAMIDE; 2 [4 (4 CHLOROPHENYL) 5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4H [1,2,4]TRIAZOL 3 YLSULFANYL] N (4 ISOPROPYLPHENYL)ACETAMIDE; 2 [4 ALLYL 5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4H [1,2,4]TRIAZOL 3 YLSULFANYL] N (3,4 DIMETHYLPHENYL)ACETAMIDE; 2 [4 ALLYL 5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4H [1,2,4]TRIAZOL 3 YLSULFANYL] N (4 ISOPROPYLPHENYL)ACETAMIDE; 2 [4 ALLYL 5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4H [1,2,4]TRIAZOL 3 YLSULFANYL] N (4 TRIFLUOROMETHYLPHENYL)ACETAMIDE; 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 (3 METHOXYPROPYL) 4H [1,2,4]TRIAZOL 3 YLSULFANYL] N (4 ISOPROPYLPHENYL)ACETAMIDE; 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 (3 METHOXYPROPYL) 4H [1,2,4]TRIAZOL 3 YLSULFANYL] N (4 TRIFLUOROMETHYLPHENYL)ACETAMIDE; 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 (4 METHOXYPHENYL) 4H [1,2,4]TRIAZOL 3 YLSULFANYL] N (4 ISOPROPYLPHENYL)ACETAMIDE; 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 (4 METHOXYPHENYL) 4H [1,2,4]TRIAZOL 3 YLSULFANYL] N (4 TRIFLUOROMETHYLPHENYL)ACETAMIDE; 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 FURAN 2 YLMETHYL 4H [1,2,4]TRIAZOL 3 YLSULFANYL] N (4 ISOPROPYLPHENYL)ACETAMIDE; 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 FURAN 2 YLMETHYL 4H [1,2,4]TRIAZOL 3 YLSULFANYL] N (4 METHYLTHIAZOL 2 YL)ACETAMIDE; 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 FURAN 2 YLMETHYL 4H [1,2,4]TRIAZOL 3 YLSULFANYL] N (4 TRIFLUOROMETHYLPHENYL)ACETAMIDE; 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 FURAN 2 YLMETHYL 4H [1,2,4]TRIAZOL 3 YLSULFANYL] N (5 METHYLISOXAZOL 3 YL)ACETAMIDE; 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 FURAN 2 YLMETHYL 4H [1,2,4]TRIAZOL 3 YLSULFANYL] N PHENYLACETAMIDE; 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 FURAN 2 YLMETHYL 4H [1,2,4]TRIAZOL 3 YLSULFANYL] N THIAZOL 2 YLACETAMIDE; 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 FURAN 2 YLMETHYL 4H [1,2,4]TRIAZOL 3 YLSULFANYL]ACETAMIDE; LIPOCORTIN 2; N (2,4 DIMETHYLPHENYL) 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 FURAN 2 YLMETHYL 4H [1,2,4]TRIAZOL 3 YLSULFANYL]ACETAMIDE; N (2,5 DIMETHYLPHENYL) 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 FURAN 2 YLMETHYL 4H [1,2,4]TRIAZOL 3 YLSULFANYL]ACETAMIDE; N (3,4 DIMETHYLPHENYL) 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 (3 METHOXYPROPYL) 4H [1,2,4]TRIAZOL 3 YLSULFANYL]ACETAMIDE; N (3,4 DIMETHYLPHENYL) 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 (4 METHOXYPHENYL) 4H [1,2,4]TRIAZOL 3 YLSULFANYL]ACETAMIDE; N (3,4 DIMETHYLPHENYL) 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 FURAN 2 YLMETHYL 4H [1,2,4]TRIAZOL 3 YLSULFANYL]ACETAMIDE; N (3,4 DIMETHYLPHENYL) 3 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 FURAN 2 YLMETHYL 4H [1,2,4]TRIAZOL 3 YLSULFANYL]PROPIONAMIDE; N (3,5 BIS TRIFLUOROMETHYLPHENYL) 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 FURAN 2 YLMETHYL 4H [1,2,4]TRIAZOL 3 YLSULFANYL]ACETAMIDE; N (4 BROMOPHENYL) 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 FURAN 2 YLMETHYL 4H [1,2,4]TRIAZOL 3 YLSULFANYL]ACETAMIDE; N (4 CHLOROPHENYL) 2 [5 (4,6 DIMETHYLPYRIMIDIN 2 YLSULFANYLMETHYL) 4 FURAN 2 YLMETHYL 4H [1,2,4]TRIAZOL 3 YLSULFANYL]ACETAMIDE; PROTEIN S 100; S100A10 PROTEIN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; COMPETITIVE BINDING ASSAY; COMPLEX FORMATION; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOLECULAR DOCKING; PROTEIN PROTEIN INTERACTION; STRUCTURE ACTIVITY RELATION;

EID: 84907502804     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.07.043     Document Type: Article

References (35)

1. S. Shangary, and S. Wang Clin. Cancer Res. 14 2008 5318
2. S. Shangary, and S. Wang Annu. Rev. Pharmacol. Toxicol. 49 2009 223
3. L. Gandhi, D.R. Camidge, M. Ribeiro de Oliveira, P. Bonomi, D. Gandara, D. Khaira, C.L. Hann, E.M. McKeegan, E. Litvinovich, P.M. Hemken, C. Dive, S.H. Enschede, C. Nolan, Y.L. Chiu, T. Busman, H. Xiong, A.P. Krivoshik, R. Humerickhouse, G.I. Shapiro, and C.M. Rudin J. Clin. Oncol. 29 2011 909
4. I. Salama, P.S. Malone, F. Mihaimeed, and J.L. Jones Eur. J. Surg. Oncol. 34 2008 357
5. L. Santamaria-Kisiel, A.C. Rintala-Dempsey, and G.S. Shaw Biochem. J. 396 2006 201
6. V. Gerke, and K. Weber EMBO J. 4 1985 2917
7. N. Johnsson, G. Marriott, and K. Weber EMBO J. 7 1988 2435
8. S. Rety, J. Sopkova, M. Renouard, D. Osterloh, V. Gerke, S. Tabaries, F. Russo-Marie, and A. Lewit-Bentley Nat. Struct. Biol. 6 1999 89
9. Q. Ling, A.T. Jacovina, A. Deora, M. Febbraio, R. Simantov, R.L. Silverstein, B. Hempstead, W.H. Mark, and K.A. Hajjar J. Clin. Invest. 113 2004 38
10. A.P. Surette, P.A. Madureira, K.D. Phipps, V.A. Miller, P. Svenningsson, and D.M. Waisman Blood 118 2011 3172
11. H.K. Myrvang, X. Guo, C. Li, and L.V. Dekker FEBS Lett. 587 2013 3210
12. T. Andey, S. Marepally, A. Patel, T. Jackson, S. Sarkar, M. O'Connell, R.C. Reddy, S. Chellappan, P. Singh, and M. Singh J. Controlled Release 184 2014 67
13. T.R.K. Reddy, C. Li, X. Guo, H.K. Myrvang, P.M. Fischer, and L.V. Dekker J. Med. Chem. 54 2011 2080
14. T.R.K. Reddy, C. Li, P.M. Fischer, and L.V. Dekker ChemMedChem 7 2012 1435
15. M.L. Verdonk, J.C. Cole, M.J. Hartshorn, C.W. Murray, and R.D. Taylor Proteins 52 2003 609
16. Girardet, J.-L.; Zhang, Z.; Hamatake, R.; de la Rosa Hernandez, M. A.; Gunic, E.; Hong, Z.; Kim, H.; Koh, Y.-H.; Nilar, S.; Shaw, S.; Yao, N. WO2,004,030,611, 2004.
17. Zelle, R.; Galullo, V. P.; Baker, C. T.; Will, P.; Frazee, W. J. WO2,005,087,750, 2005.
18. M.O. Contour-Galcera, A. Sidhu, P. Plas, and P. Roubert Bioorg. Med. Chem. Lett. 15 2005 3555
19. M.C. Sarva, G. Romeo, F. Guerrera, M. Siracusa, L. Salerno, F. Russo, A. Cagnotto, M. Goegan, and T. Mennini Bioorg. Med. Chem. 10 2002 313
20. J.P. Marino Jr., P.W. Fisher, G.A. Hofmann, R.B. Kirkpatrick, C.A. Janson, R.K. Johnson, C. Ma, M. Mattern, T.D. Meek, M.D. Ryan, C. Schulz, W.W. Smith, D.G. Tew, T.A. Tomazek Jr., D.F. Veber, W.C. Xiong, Y. Yamamoto, K. Yamashita, G. Yang, and S.K. Thompson J. Med. Chem. 50 2007 3777
21. M. Lazarevic, V. Dimova, D.M. Gabor, V. Kakurinov, and K.C. Ragenovic Heterocycl. Commun. 7 2001 577
22. E. Bednarek, B. Modzelewska-Banachiewicz, M.K. Cyranski, J. Sitkowski, and I. Wawer J. Mol. Struct. 562 2001 167
23. Z. Wang, B. Wu, K.L. Kuhen, B. Bursulaya, T.N. Nguyen, D.G. Nguyen, and Y. He Bioorg. Med. Chem. Lett. 16 2006 4174
24. J.M. Kane, M.A. Staeger, C.R. Dalton, F.P. Miller, M.W. Dudley, A.M. Ogden, J.H. Kehne, H.J. Ketteler, T.C. McCloskey, and Y. Senyah J. Med. Chem. 37 1994 125
25. M. De La Rosa, H.W. Kim, E. Gunic, C. Jenket, U. Boyle, Y.H. Koh, I. Korboukh, M. Allan, W. Zhang, H. Chen, W. Xu, S. Nilar, N. Yao, R. Hamatake, S.A. Lang, Z. Hong, Z. Zhang, and J.L. Girardet Bioorg. Med. Chem. Lett. 16 2006 4444
26. L. Navidpour, H. Shafaroodi, K. Abdi, M. Amini, M.H. Ghahremani, A.R. Dehpour, and A. Shafiee Bioorg. Med. Chem. 14 2006 2507
27. I. Kucukguzel, E. Tatar, S.G. Kucukguzel, S. Rollas, and E. De Clercq Eur. J. Med. Chem. 43 2008 381
28. H.L. Sham, D.A. Betebenner, X. Chen, A. Saldivar, S. Vasavanonda, D.J. Kempf, J.J. Plattner, and D.W. Norbeck Bioorg. Med. Chem. Lett. 12 2002 1185
29. I.R. Ezabadi, C. Camoutsis, P. Zoumpoulakis, A. Geronikaki, M. Sokovic, J. Glamocilija, and A. Ciric Bioorg. Med. Chem. 16 2008 1150
30. M.D. Mullican, M.W. Wilson, D.T. Connor, C.R. Kostlan, D.J. Schrier, and R.D. Dyer J. Med. Chem. 36 1993 1090
31. M.E. Theoclitou, N.G. Delaet, and L.A. Robinson J. Comb. Chem. 4 2002 315
32. X. Collin, A. Sauleau, and J. Coulon Bioorg. Med. Chem. Lett. 13 2003 2601
33. G. Turan-Zitouni, Z.A. Kaplancikli, M.T. Yildiz, P. Chevallet, and D. Kaya Eur. J. Med. Chem. 40 2005 607
34. T. Becker, K. Weber, and N. Johnsson EMBO J. 9 1990 4207
35. C. Li, T.R.K. Reddy, P.M. Fischer, and L.V. Dekker Assay Drug Dev. Technol. 8 2010 85