Short cut to 1,2,3-triazole-based p38 MAP kinase inhibitors via [3+2]-cycloaddition chemistry

New Journal of Chemistry

Volumn 33, Issue 5, 2009, Pages 1010-1016

  Dinér, Peter ^a   Andersson, Terese ^a   Kjellén, Jimmy ^a   Elbing, Karin ^a   Hohmann, Stefan ^a   Grøtli, Morten ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

1 (CYCLOPROPYLMETHYL) 4 (4 FLUOROPHENYL) 5 (PYRIDIN 4 YL) 1H 1,2,3 TRIAZOLE; 1 BENZYL 4 (4 BROMOPHENYL) 5 (PYRIDIN 4 YL) 1H 1,2,3 TRIAZOLE; 1 BENZYL 4 (4 CHLOROPHENYL) 5 (PYRIDIN 4 YL) 1H 1,2,3 TRIAZOLE; 1 BENZYL 4 (4 FLUOROPHENYL) 5 (PYRIDIN 4 YL) 1H 1,2,3 TRIAZOLE; 1 BENZYL 4 PHENYL 5 (PYRIDIN 4 YL) 1H 1,2,3 TRIAZOLE; 1,2,3 TRIAZOLE DERIVATIVE; 2 [4 (4 FLUOROPHENYL) 5 (PYRIDIN 4 YL) 1H 1,2,3 TRIAZOL 1 YL] 3 (1H INDOL 3 YL)PROPANOIC ACID; 2 [4 (4 FLUOROPHENYL) 5 (PYRIDIN 4 YL) 1H 1,2,3 TRIAZOL 1 YL] 3 METHYLBUTAN 1 OL; 2 [4 (4 FLUOROPHENYL) 5 (PYRIDIN 4 YL) 1H 1,2,3 TRIAZOL 1 YL] 3 PHENYLPROPAN 1 OL; 4 (4 FLUOROPHENYL) 2 (4 METHYLSULFINYLPHENYL) 5 (4 PYRIDYL)IMIDAZOLE; 5 (2 AMINO 4 PYRIMIDINYL) 4 (4 FLUOROPHENYL) 1 (4 PIPERIDINYL)IMIDAZOLE; COPPER; MITOGEN ACTIVATED PROTEIN KINASE P38 INHIBITOR; SB 216995; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; DRUG DESIGN; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; PRIORITY JOURNAL; SUZUKI REACTION;

EID: 70349200262     PISSN: 11440546     EISSN: 13699261     Source Type: Journal    
DOI: 10.1039/b818909a     Document Type: Article

References (26)

1. Z. Chen T. B. Gibson F. Robinson L. Silvestro G. Pearson B. Xu A. Wright C. Vanderbilt M. H. Cobb Chem. Rev. 2001 101 2449 2476
2. R. Buijsman, in Chemogenomics in Drug Discovery: A Medicinal Chemistry Perspective, ed., H. Kubinyi, and, G. Müller, Wiley-VCH Verlag GmbH & Co, Weinheim, 2004
3. C. Dominguez N. Tamayo D. W. Zhang Expert Opin. Ther. Pat. 2005 15 801 816
4. J. Hynes K. Leftheris Curr. Top. Med. Chem. 2005 5 967 985
5. S. T. Wrobleski A. M. Doweyko Curr. Top. Med. Chem. 2005 5 1005 1016
6. A. Cuenda J. Rouse Y. N. Doza R. Meier P. Cohen T. F. Gallagher P. R. Young J. C. Lee FEBS Lett. 1995 364 229 233
7. P. R. Young M. M. McLaughlin S. Kumar S. Kassis M. L. Doyle D. McNulty T. F. Gallagher S. Fisher P. C. McDonnell S. A. Carr M. J. Huddleston G. Seibel T. G. Porter G. P. Livi J. L. Adams J. C. Lee J. Biol. Chem. 1997 272 12116 12121
8. C. W. Tornoe C. Christensen M. Meldal J. Org. Chem. 2002 67 3057 3064
9. V. V. Rostovtsev L. G. Green V. V. Fokin K. B. Sharpless Angew. Chem., Int. Ed. 2002 41 2596 2599
10. P. Wu V. V. Fokin Aldrichimica Acta 2007 40 7 17
11. L. V. Lee M. L. Mitchell S. J. Huang V. V. Fokin K. B. Sharpless C. H. Wong J. Am. Chem. Soc. 2003 125 9588 9589
12. Q. Wang T. R. Chan R. Hilgraf V. V. Fokin K. B. Sharpless M. G. Finn J. Am. Chem. Soc. 2003 125 3192 3193
13. A. Brik J. Muldoon Y. C. Lin J. H. Elder D. S. Goodsell A. J. Olson V. V. Fokin K. B. Sharpless C. H. Wong ChemBioChem 2003 4 1246 1248
14. Z. Wang B. J. Canagarajah J. C. Boehm S. Kassisa M. H. Cobb P. R. Young S. Abdel-Meguid J. L. Adams E. J. Goldsmith Structure 1998 6 1117 1128
15. Macromodel [9.1], Schrödinger, LLC., New York, 2007
16. Glide [4.0], Schrödinger, LLC., New York, 2005
17. M. M. Sá M. D. Ramos L. Fernandes Tetrahedron 2006 62 11652 11656
18. S. K. Ramanathan J. Keeler H. L. Lee D. S. Reddy G. Lushington J. Aube Org. Lett. 2005 7 1059 1062
19. A. Paul H. Bittermann P. Gmeiner Tetrahedron 2006 62 8919 8927
20. Y. M. Wu J. Deng Y. Li Q. Y. Chen Synthesis 2005 1314 1318
21. A. D. Becke J. Chem. Phys. 1993 98 1372 1377
22. C. Lee W. Yang R. G. Parr Phys. Rev. B: Condens. Matter Mater. Phys. 1988 37 785 789
23. P. J. Stephens F. J. Devlin C. F. Chabalowski M. J. Frisch J. Phys. Chem. 1994 98 11623 11627
24. P. C. Hariharan J. A. Pople Theor. Chim. Acta 1973 28 213 222
25. M. M. Francl W. J. Pietro W. J. Hehre J. S. Binkley M. S. Gordon D. J. DeFrees J. A. Pople J. Chem. Phys. 1982 77 3654 3665
26. Jaguar 7.0, Schrödinger, LLC., Portland, 2007