Design, synthesis, and biological evaluation of novel 2-pyridinyl-[1,2,4] triazoles as inhibitors of transforming growth factor β1 type 1 receptor

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 9, 2004, Pages 2013-2020

  Kim, Dae Kee ^a   Kim, Joonseop ^a   Park, Hyun Ju ^b  

^a Ewha Womans University   (South Korea)

^b Sungkyunkwan University   (South Korea)

Author keywords

2 Pyridinyl 1,2,4 triazoles; ALK5; Inhibitors; TGF 1 type 1 receptor

Indexed keywords

4 (1 BENZO[1,3]DIOXOL 5 YL 5 PYRIDIN 2 YL 1H [1,2,4]TRIAZOL 3 YL)BENZAMIDE; 4 (1 BENZO[1,3]DIOXOL 5 YL 5 PYRIDIN 2 YL 1H [1,2,4]TRIAZOL 3 YL)BENZONITRILE; 4 (1 PYRIDIN 2 YL 5 QUINOXALIN 6 YL 1H [1,2,4]TRIAZOL 3 YL)BENZAMIDE; 4 (1 PYRIDIN 2 YL 5 QUINOXALIN 6 YL 1H [1,2,4]TRIAZOL 3 YL)BENZONITRILE; 4 (5 BENZO[1,3]DIOXOL 5 YL 1 PYRIDIN 2 YL 1H [1,2,4]TRIAZOL 3 YL)BENZAMIDE; 4 (5 BENZO[1,3]DIOXOL 5 YL 1 PYRIDIN 2 YL 1H [1,2,4]TRIAZOL 3 YL)BENZONITRILE; 4 [1 (4 METHOXYPHENYL) 5 (6 METHYLPYRIDIN 2 YL) 1H [1,2,4]TRIAZOL 3 YL]BENZAMIDE; 4 [1 (4 METHOXYPHENYL) 5 (6 METHYLPYRIDIN 2 YL) 1H [1,2,4]TRIAZOL 3 YL]BENZONITRILE; 4 [1 (4 METHOXYPHENYL) 5 PYRIDIN 2 YL 1H [1,2,4]TRIAZOL 3 YL]BENZAMIDE; 4 [1 (4 METHOXYPHENYL) 5 PYRIDIN 2 YL 1H [1,2,4]TRIAZOL 3 YL]BENZONITRILE; 4 [1 (6 METHYLPYRIDIN 2 YL) 5 QUINOXALIN 6 YL 1H [1,2,4]TRIAZOL 3 YL]BENZAMIDE; 4 [1 (6 METHYLPYRIDIN 2 YL) 5 QUINOXALIN 6 YL 1H [1,2,4]TRIAZOL 3 YL]BENZONITRILE; 4 [1 BENZO[1,3]DIOXOL 5 YL 5 (6 METHYLPYRIDIN 2 YL) 1H [1,2,4]TRIAZOL 3 YL]BENZAMIDE; 4 [1 BENZO[1,3]DIOXOL 5 YL 5 (6 METHYLPYRIDIN 2 YL) 1H [1,2,4]TRIAZOL 3 YL]BENZONITRILE; 4 [4 (1,3 BENZODIOXOL 5 YL) 5 (2 PYRIDINYL) 1H IMIDAZOL 2 YL]BENZAMIDE; 4 [5 (4 METHOXYPHENYL) 1 (6 METHYLPYRIDIN 2 YL) 1H [1,2,4]TRIAZOL 3 YL]BENZAMIDE; 4 [5 (4 METHOXYPHENYL) 1 (6 METHYLPYRIDIN 2 YL) 1H [1,2,4]TRIAZOL 3 YL]BENZONITRILE; 4 [5 (4 METHOXYPHENYL) 1 PYRIDIN 2 YL 1H [1,2,4]TRIAZOL 3 YL]BENZAMIDE; 4 [5 (4 METHOXYPHENYL) 1 PYRIDIN 2 YL 1H [1,2,4]TRIAZOL 3 YL]BENZONITRILE; 4 [5 BENZO[1,3]DIOXOL 5 YL 1 (6 METHYLPYRIDIN 2 YL) 1H [1,2,4]TRIAZOL 3 YL]BENZAMIDE; 4 [5 BENZO[1,3]DIOXOL 5 YL 1 (6 METHYLPYRIDIN 2 YL) 1H [1,2,4]TRIAZOL 3 YL]BENZONITRILE; MITOGEN ACTIVATED PROTEIN KINASE INHIBITOR; RECEPTOR BLOCKING AGENT; TRANSFORMING GROWTH FACTOR BETA RECEPTOR; TRANSFORMING GROWTH FACTOR BETA RECEPTOR BLOCKING AGENT; TRANSFORMING GROWTH FACTOR BETA1 RECEPTOR; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG EFFECT; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL;

MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; RECEPTORS, TRANSFORMING GROWTH FACTOR BETA; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TRIAZOLES;

EID: 1842636360     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.03.004     Document Type: Article

References (21)

1. Franklin T.J. Int. J. Biochem. Cell Biol. 29:1997;79.
2. Branton M.H., Kopp J.B. Microbes Infect. 1:1999;1349.
3. Sime P.J., O'Reilly K.M.A. Clin. Immunol. 99:2001;308.
4. Giri S.N. Annu. Rev. Pharmacol. Toxicol. 43:2003;73.
5. Massagué J. Annu. Rev. Biochem. 67:1998;753.
6. Lutz M., Knaus P. Cell. Signal. 14:2002;977.
7. Wang Z., Canagarajah B.J., Boehm J.C., Kassisa S., Cobb M.H., Young P.R., Abdel-Meguid S., Adams J.L., Goldsmith E.J. Structure (London). 6:1998;1117.
8. Gallagher T.F., Seibel G.L., Kassis S., Laydon J.T., Blumenthal M.J., Lee J.C., Lee D., Boehm J.C., Fier-Thompson S.M., Abt J.W., Sorenson M.E., Smietana J.M., Hall R.F., Garigipati R.S., Bender P.E., Erhard K.F., Krog A.J., Hofmann G.A., Sheldrake P.L., McDonnell P.C., Kumar S., Young P.R., Adams J.L. Bioorg. Med. Chem. 5:1997;49.
9. Eyers P.A., Craxton M., Morrice N., Cohen P., Goedert M. Chem. Biol. 5:1998;321.
10. Callahan J.F., Burgess J.L., Fornwald J.A., Gaster L.M., Harling J.D., Harrington F.P., Heer J., Kwon C., Lehr R., Mathur A., Olson B.A., Weinstock J., Laping N.J. J. Med. Chem. 45:2002;999.
11. Inman G.J., Nicoĺas F.J., Callahan J.F., Harling J.D., Gaster L.M., Reith A.D., Laping N.J., Hill C.S. Mol. Pharmacol. 62:2002;65.
12. Izawa, T.; Kashiwabara, T.; Nakajima, S.; Ogawa, N. Eur. Patent 388,528 A2, 1990
13. Freudenberg K., Fischer E. Chem. Ber. 89:1956;1230.
14. Harling, J. D.; Gaster, L.M. WO 2001072737 A1, 2001
15. Copp, F. C.; Caldwell, A. G.; Collard, D. Eur. Patent 55,418 A2, 1982
16. Baccar B.G., Barrans J. Compt. Rend. 259:1964;1340.
17. Dennler S., Itoh S., Vivien D., ten Dijke P., Huet S., Gauthier J.M. EMBO J. 17:1998;3091.
18. Wrana J.L., Attisano L., Carcamo J., Zentella A., Doody J., Laiho M., Wang X.F., Massagué J. Cell. 71:1992;1003.
19. Huse M., Muir T.W., Xu L., Chen Y.-G., Kuriyan J., Massagúe J. Mol. Cell. 8:2001;671.
20. Yakymovych I., Engström U., Grimsby S., Heldin C.-H., Souchelnytskyi S. Biochemistry. 41:2002;11000.
21. Jones T.A., Zou J.Y., Cowan S.W., Kjeldgaard M. Acta Crystallogr. A. 47:1991;110.