SCOPUS 정보 검색 플랫폼

Volumn 19, Issue 8, 2011, Pages 2633-2640

Synthesis and biological evaluation of 1-substituted-3(5)-(6-methylpyridin- 2-yl)-4-(quinolin-6-yl)pyrazoles as transforming growth factor-β type 1 receptor kinase inhibitors

(9) Jin, Cheng Hua a Krishnaiah, Maddeboina a Sreenu, Domalapally a Rao, Kota Sudhakar a Subrahmanyam, Vura Bala a Park, Chul Yong a Son, Jee Yeon a Sheen, Yhun Yhong a Kim, Dae Kee a

a Ewha Womans University (South Korea)

Author keywords

ALK5 inhibitor; Cancer; Cell based luciferase reporter assay; Fibrosis; Kinase assay; TGF

Indexed keywords

2 [3 (6 METHYLPYRIDIN 2 YL) 4 (QUINOLIN 6 YL) 1H PYRAZOL 1 YL] N PHENYLACETAMIDE; 2 [3 (6 METHYLPYRIDIN 2 YL) 4 (QUINOLIN 6 YL) 1H PYRAZOL 1 YL] N PHENYLETHANETHIOAMIDE; 2 [4 (4 METHOXYQUINOLIN 6 YL) 3 (6 METHYLPYRIDIN 2 YL) 1H PYRAZOL 1 YL] N PHENYLACETAMIDE; 2 [4 (4 METHOXYQUINOLIN 6 YL) 5 (6 METHYLPYRIDIN 2 YL) 1H PYRAZOL 1 YL] N PHENYLACETAMIDE; 2 [5 (6 METHYLPYRIDIN 2 YL) 4 (QUINOLIN 6 YL) 1H PYRAZOL 1 YL] N PHENYLACETAMIDE; 3 (3 CYANOPHENYL) 3 [3 (6 METHYLPYRIDIN 2 YL) 4 (QUINOLIN 6 YL) 1H PYRAZOL 1 YL]PROPANAMIDE; 3 [2 [3 (6 METHYLPYRIDIN 2 YL) 4 (QUINOLIN 6 YL) 1H PYRAZOL YL] 1H PYRAZOL ACETAMIDO]BENZAMIDE; 3 [2 [5 (6 METHYLPYRIDIN 2 YL) 4 (QUINOLIN 6 YL) 1H PYRAZOL 1 YL]ACETAMIDO]BENZAMIDE; 3 [3 (6 METHYLPYRIDIN 2 YL) 4 (QUINOLIN 6 YL) 1H PYRAZOL 1 YL] N PHENYLPROPANAMIDE; 3 [3 (6 METHYLPYRIDIN 2 YL) 4 (QUINOLIN 6 YL) 1H PYRAZOL 1 YL] N PHENYLPROPANETHIOAMIDE; 3(5) (6 METHYLPYRIDIN 2 YL) 4 (QUINOLIN 6 YL)PYRAZOLE DERIVATIVE; LUCIFERASE; N (3 CYANOPHENYL) 2 [3 (6 METHYLPYRIDIN 2 YL) 4 (QUINOLIN 6 YL) 1H PYRAZOL 1 YL]ACETAMIDE; N (3 CYANOPHENYL) 2 [3 (6 METHYLPYRIDIN 2 YL) 4 (QUINOLIN 6 YL) 1H PYRAZOL 1 YL]ETHANETHIOAMIDE; N (3 CYANOPHENYL) 2 [4 (4 METHOXYQUINOLIN 6 YL) 3 (6 METHYLPYRIDIN 2 YL) 1H PYRAZOL 1 YL]ACETAMIDE; N (3 CYANOPHENYL) 2 [4 (4 METHOXYQUINOLIN 6 YL) 5 (6 METHYLPYRIDIN 2 YL) 1H PYRAZOL 1 YL]ACETAMIDE; N (3 CYANOPHENYL) 2 [5 (6 METHYLPYRIDIN 2 YL) 4 (QUINOLIN 6 YL) 1H PYRAZOL 1 YL]ACETAMIDE; N (3 CYANOPHENYL) 3 [3 (6 METHYLPYRIDIN 2 YL) 4 (QUINOLIN 6 YL) 1H PYRAZOL 1 YL]PROPANAMIDE; N (3 CYANOPHENYL) 3 [3 (6 METHYLPYRIDIN 2 YL) 4 (QUINOLIN 6 YL) 1H PYRAZOL 1 YL]PROPANETHIOAMIDE; N (3 CYANOPHENYL) 3 [4 (4 METHOXYQUINOLIN 6 YL) 3 (6 METHYLPYRIDIN 2 YL) 1H PYRAZOL 1 YL]PROPANAMIDE; PROTEIN TYROSINE KINASE INHIBITOR; TRANSFORMING GROWTH FACTOR BETA RECEPTOR 1; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ASSAY; ENZYME INHIBITION; ENZYME PHOSPHORYLATION; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; IC 50; KERATINOCYTE; PROTON NUCLEAR MAGNETIC RESONANCE; REPORTER GENE;

CELL LINE; ENZYME ASSAYS; HUMANS; PHOSPHORYLATION; PROTEIN KINASE INHIBITORS; PROTEIN-SERINE-THREONINE KINASES; PYRAZOLES; RECEPTORS, TRANSFORMING GROWTH FACTOR BETA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79954425264 PISSN: 09680896 EISSN: None Source Type: Journal
DOI: 10.1016/j.bmc.2011.03.008 Document Type: Article

Times cited : (31)

References (40)

1
- 0031438047
- C.H. Heldin, K. Miyazono, and P. Ten Dijke Nature 390 1997 465
- (1997) Nature , vol.390 , pp. 465
- Heldin, C.H.¹ Miyazono, K.² Ten Dijke, P.³

2
- 0038682002
- J. Shi, and J. Massague Cell 113 2003 685
- (2003) Cell , vol.113 , pp. 685
- Shi, J.¹ Massague, J.²

3
- 0034574298
- J. Massague Nat. Rev. Mol. Cell Biol. 1 2000 169
- (2000) Nat. Rev. Mol. Cell Biol. , vol.1 , pp. 169
- Massague, J.¹

4
- 0142104985
- R. Derynck, and Y.E. Zhang Nature 425 2003 577
- (2003) Nature , vol.425 , pp. 577
- Derynck, R.¹ Zhang, Y.E.²

5
- 14844337071
- W. Wang, V. Koka, and H.Y. Lan Nephrology 10 2005 48
- (2005) Nephrology , vol.10 , pp. 48
- Wang, W.¹ Koka, V.² Lan, H.Y.³

6
- 33751302009
- H. Lim, and Y.Z. Zhu Cell. Mol. Life Sci. 63 2006 2584
- (2006) Cell. Mol. Life Sci. , vol.63 , pp. 2584
- Lim, H.¹ Zhu, Y.Z.²

7
- 33847210725
- L. Gu, Y.-J. Zhu, X. Yang, Z.-J. Guo, W.-B. Xu, and X.-L. Tian Acta Pharmacol. Sin. 28 2007 382
- (2007) Acta Pharmacol. Sin. , vol.28 , pp. 382
- Gu, L.¹ Zhu, Y.-J.² Yang, X.³ Guo, Z.-J.⁴ Xu, W.-B.⁵ Tian, X.-L.⁶

8
- 2642585736
- F.W. Shek, and R.C. Benyon Eur. J. Gastroenterol. Hepatol. 16 2004 123
- (2004) Eur. J. Gastroenterol. Hepatol. , vol.16 , pp. 123
- Shek, F.W.¹ Benyon, R.C.²

9
- 33745515023
- B. Bierie, and H.L. Moses Nat. Rev. Cancer 6 2006 506
- (2006) Nat. Rev. Cancer , vol.6 , pp. 506
- Bierie, B.¹ Moses, H.L.²

10
- 30944441065
- S.G. Rane, J.-H. Lee, and H.-M. Lin Cytokine Growth Factor Rev. 17 2006 107
- (2006) Cytokine Growth Factor Rev. , vol.17 , pp. 107
- Rane, S.G.¹ Lee, J.-H.² Lin, H.-M.³

11
- 33745082823
- M. Dong, and G.C. Blobe Blood 107 2006 4589
- (2006) Blood , vol.107 , pp. 4589
- Dong, M.¹ Blobe, G.C.²

12
- 20344385003
- S.K. Halder, R.D. Beauchamp, and P.K. Datta Neoplasia 7 2005 509
- (2005) Neoplasia , vol.7 , pp. 509
- Halder, S.K.¹ Beauchamp, R.D.² Datta, P.K.³

13
- 1342265719
- S.D. Byfield, C. Major, N.J. Laping, and A.B. Roberts Mol. Pharmacol. 65 2004 744
- (2004) Mol. Pharmacol. , vol.65 , pp. 744
- Byfield, S.D.¹ Major, C.² Laping, N.J.³ Roberts, A.B.⁴

14
- 19944421105
- A.C. De Gouville, V. Boullay, G. Krysa, J. Pilot, J.M. Brusq, F. Loriolle, J.M. Gauthier, S.A. Papworth, A. Laroze, F. Gellibert, and S. Huet Br. J. Pharmacol. 145 2005 166
- (2005) Br. J. Pharmacol. , vol.145 , pp. 166
- De Gouville, A.C.¹ Boullay, V.² Krysa, G.³ Pilot, J.⁴ Brusq, J.M.⁵ Loriolle, F.⁶ Gauthier, J.M.⁷ Papworth, S.A.⁸ Laroze, A.⁹ Gellibert, F.¹⁰ Huet, S.¹¹

15
- 33751320565
- R. Ge, V. Rajeev, P. Ray, E. Lattime, S. Rittling, S. Medicherla, A. Protter, A. Murphy, J. Chakravarty, S. Dugar, G. Schreiner, N. Barnard, and M. Reiss Clin. Cancer Res. 12 2006 4315
- (2006) Clin. Cancer Res. , vol.12 , pp. 4315
- Ge, R.¹ Rajeev, V.² Ray, P.³ Lattime, E.⁴ Rittling, S.⁵ Medicherla, S.⁶ Protter, A.⁷ Murphy, A.⁸ Chakravarty, J.⁹ Dugar, S.¹⁰ Schreiner, G.¹¹ Barnard, N.¹² Reiss, M.¹³

16
- 33746265817
- A.M. Kapoun, N.J. Gaspar, Y. Wang, D. Damm, Y.-W. Liu, G. O'Young, D. Quon, A. Lam, K. Munson, T.-T. Tran, J.Y. Ma, A. Murphy, S. Dugar, S. Chakravarty, A.A. Protter, F.-Q. Wen, X. Liu, S.I. Rennard, and L.S. Higgins Mol. Pharmacol. 70 2006 518
- (2006) Mol. Pharmacol. , vol.70 , pp. 518
- Kapoun, A.M.¹ Gaspar, N.J.² Wang, Y.³ Damm, D.⁴ Liu, Y.-W.⁵ O'Young, G.⁶ Quon, D.⁷ Lam, A.⁸ Munson, K.⁹ Tran, T.-T.¹⁰ Ma, J.Y.¹¹ Murphy, A.¹² Dugar, S.¹³ Chakravarty, S.¹⁴ Protter, A.A.¹⁵ Wen, F.-Q.¹⁶ Liu, X.¹⁷ Rennard, S.I.¹⁸ Higgins, L.S.¹⁹

17
- 79954425621
- Mundla, S. R. PCT Int. Appl. WO 2007018818 A1, 2007.
- (2007) PCT Int. Appl. WO 2007018818 A1
- Mundla, S.R.¹

18
- 1942534588
- D.-K. Kim, J. Kim, and H.-J. Park Bioorg. Med. Chem. Lett. 14 2004 2401
- (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 2401
- Kim, D.-K.¹ Kim, J.² Park, H.-J.³

19
- 1842636360
- D.-K. Kim, J. Kim, and H.-J. Park Bioorg. Med. Chem. 12 2004 2013
- (2004) Bioorg. Med. Chem. , vol.12 , pp. 2013
- Kim, D.-K.¹ Kim, J.² Park, H.-J.³

20
- 34347242484
- D.-K. Kim, Y. Jang, H.S. Lee, H.-J. Park, and J. Yoo J. Med. Chem. 50 2007 3143
- (2007) J. Med. Chem. , vol.50 , pp. 3143
- Kim, D.-K.¹ Jang, Y.² Lee, H.S.³ Park, H.-J.⁴ Yoo, J.⁵

21
- 40849097867
- D.-K. Kim, J.H. Choi, Y.J. An, and H.S. Lee Bioorg. Med. Chem. Lett. 18 2008 2122
- (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 2122
- Kim, D.-K.¹ Choi, J.H.² An, Y.J.³ Lee, H.S.⁴

22
- 60349088674
- D.-K. Kim, S.H. Jung, H.S. Lee, and P.M. Dewang Eur. J. Med. Chem. 44 2009 568
- (2009) Eur. J. Med. Chem. , vol.44 , pp. 568
- Kim, D.-K.¹ Jung, S.H.² Lee, H.S.³ Dewang, P.M.⁴

23
- 77953873137
- P.M. Dewang, and D.-K. Kim Bioorg. Med. Chem. Lett. 20 2010 4228
- (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 4228
- Dewang, P.M.¹ Kim, D.-K.²

24
- 77953231559
- D.-K. Kim, Y.-I. Lee, Y.W. Lee, P.M. Dewang, Y.Y. Sheen, Y.W. Kim, H.-J. Park, J. Yoo, H.S. Lee, and Y.-K. Kim Bioorg. Med. Chem. 18 2010 4459
- (2010) Bioorg. Med. Chem. , vol.18 , pp. 4459
- Kim, D.-K.¹ Lee, Y.-I.² Lee, Y.W.³ Dewang, P.M.⁴ Sheen, Y.Y.⁵ Kim, Y.W.⁶ Park, H.-J.⁷ Yoo, J.⁸ Lee, H.S.⁹ Kim, Y.-K.¹⁰

25
- 39349112853
- Y.W. Kim, Y.K. Kim, J.Y. Lee, K.T. Chang, H.J. Lee, D.-K. Kim, and Y.Y. Sheen Xenobiotica 38 2008 325
- (2008) Xenobiotica , vol.38 , pp. 325
- Kim, Y.W.¹ Kim, Y.K.² Lee, J.Y.³ Chang, K.T.⁴ Lee, H.J.⁵ Kim, D.-K.⁶ Sheen, Y.Y.⁷

26
- 42249101381
- Y.W. Kim, Y.K. Kim, D.-K. Kim, and Y.Y. Sheen Xenobiotica 38 2008 451 23
- (2008) Xenobiotica , vol.38 , pp. 451
- Kim, Y.W.¹ Kim, Y.K.² Kim, D.-K.³ Sheen, Y.Y.⁴

27
- 33748939751
- J.-A. Moon, H.-T. Kim, I.-S. Cho, Y.Y. Sheen, and D.-K. Kim Kidney Int. 70 2006 1234
- (2006) Kidney Int. , vol.70 , pp. 1234
- Moon, J.-A.¹ Kim, H.-T.² Cho, I.-S.³ Sheen, Y.Y.⁴ Kim, D.-K.⁵

28
- 36049051243
- J. Luo, P.P. Ho, M.S. Buckwalter, T. Hsu, L.Y. Lee, H. Zhang, D.-K. Kim, S.-J. Kim, S.S. Gambhir, L. Steinman, and T. Wyss-Coray J. Clin. Invest. 117 2007 3306
- (2007) J. Clin. Invest. , vol.117 , pp. 3306
- Luo, J.¹ Ho, P.P.² Buckwalter, M.S.³ Hsu, T.⁴ Lee, L.Y.⁵ Zhang, H.⁶ Kim, D.-K.⁷ Kim, S.-J.⁸ Gambhir, S.S.⁹ Steinman, L.¹⁰ Wyss-Coray, T.¹¹

29
- 65149083193
- J.-K. Ryu, S. Piao, H.-Y. Shin, M.J. Choi, L.W. Zhang, H.-R. Jin, W.J. Kim, J.-Y. Han, S.S. Hong, S.H. Park, S.-J. Lee, I.-H. Kim, C.R. Lee, D.-K. Kim, M. Mamura, S.-J. Kim, and J.-K. Suh J. Sex. Med. 6 2009 1284
- (2009) J. Sex. Med. , vol.6 , pp. 1284
- Ryu, J.-K.¹ Piao, S.² Shin, H.-Y.³ Choi, M.J.⁴ Zhang, L.W.⁵ Jin, H.-R.⁶ Kim, W.J.⁷ Han, J.-Y.⁸ Hong, S.S.⁹ Park, S.H.¹⁰ Lee, S.-J.¹¹ Kim, I.-H.¹² Lee, C.R.¹³ Kim, D.-K.¹⁴ Mamura, M.¹⁵ Kim, S.-J.¹⁶ Suh, J.-K.¹⁷

30
- 55649112720
- G.T. Lee, J.H. Hong, T.J. Mueller, J.A. Watson, C. Kwak, Y.Y. Sheen, D.-K. Kim, S.J. Kim, and I.Y. Kim J. Urol. 180 2008 2660
- (2008) J. Urol. , vol.180 , pp. 2660
- Lee, G.T.¹ Hong, J.H.² Mueller, T.J.³ Watson, J.A.⁴ Kwak, C.⁵ Sheen, Y.Y.⁶ Kim, D.-K.⁷ Kim, S.J.⁸ Kim, I.Y.⁹

31
- 61349100681
- L. Long, A. Crosby, X. Yang, M. Southwood, P.D. Upton, D.-K. Kim, and N.W. Morrell Circulation 119 2009 566
- (2009) Circulation , vol.119 , pp. 566
- Long, L.¹ Crosby, A.² Yang, X.³ Southwood, M.⁴ Upton, P.D.⁵ Kim, D.-K.⁶ Morrell, N.W.⁷

32
- 77950415363
- J.H. Kim, H.-Y. Song, J.-H. Park, H.-J. Yoon, H.G. Park, and D.-K. Kim Radiology 255 2010 75
- (2010) Radiology , vol.255 , pp. 75
- Kim, J.H.¹ Song, H.-Y.² Park, J.-H.³ Yoon, H.-J.⁴ Park, H.G.⁵ Kim, D.-K.⁶

33
- 29644443725
- M. Tojo, Y. Hamashima, A. Hanyu, T. Kajimoto, M. Saitoh, K. Miyazono, M. Node, and T. Imamura Cancer Sci. 96 2005 791
- (2005) Cancer Sci. , vol.96 , pp. 791
- Tojo, M.¹ Hamashima, Y.² Hanyu, A.³ Kajimoto, T.⁴ Saitoh, M.⁵ Miyazono, K.⁶ Node, M.⁷ Imamura, T.⁸

34
- 71849097295
- WO 2004/026306 A2
- Munchhof, M. J.; Blumberg, L. C. PCT Int. Appl. WO 2004/026306 A2, 2004.
- (2004) PCT Int. Appl.
- Munchhof, M.J.¹ Blumberg, L.C.²

35
- 79954415025
- G.B. Pier, P. Delia, A.T. Mojgan, F. Francesca, S. Giulia, B. Stefania, R. Romeo, R.M. Allan, G. Stefania, V. Katia, and A.B. Pier Bioorg. Med. Chem. 15 2007 2514
- (2007) Bioorg. Med. Chem. , vol.15 , pp. 2514
- Pier, G.B.¹ Delia, P.² Mojgan, A.T.³ Francesca, F.⁴ Giulia, S.⁵ Stefania, B.⁶ Romeo, R.⁷ Allan, R.M.⁸ Stefania, G.⁹ Katia, V.¹⁰ Pier, A.B.¹¹

36
- 71749089240
- L. Zhang, H. Li, Q. Zhu, J. Liu, L. Chen, Y. Leng, H. Jiang, and H. Liu Bioorg. Med. Chem. 17 2009 7301
- (2009) Bioorg. Med. Chem. , vol.17 , pp. 7301
- Zhang, L.¹ Li, H.² Zhu, Q.³ Liu, J.⁴ Chen, L.⁵ Leng, Y.⁶ Jiang, H.⁷ Liu, H.⁸

37
- 0347059108
- W.A. Jacobs, and M. Heidelberger J. Am. Chem. Soc. 39 1917 1439
- (1917) J. Am. Chem. Soc. , vol.39 , pp. 1439
- Jacobs, W.A.¹ Heidelberger, M.²

38
- 33644759169
- R. Rajavel, U. Mahesh, and Q.Y. Shao Org. Lett. 8 2006 713
- (2006) Org. Lett. , vol.8 , pp. 713
- Rajavel, R.¹ Mahesh, U.² Shao, Q.Y.³

39
- 0026496172
- J.L. Wrana, L. Attisano, J. Carcamo, A. Zentella, J. Doody, M. Laiho, X.F. Wang, and J. Massague Cell 71 1992 1003
- (1992) Cell , vol.71 , pp. 1003
- Wrana, J.L.¹ Attisano, L.² Carcamo, J.³ Zentella, A.⁴ Doody, J.⁵ Laiho, M.⁶ Wang, X.F.⁷ Massague, J.⁸

40
- 0032102902
- P.A. Eyers, M. Craxton, N. Morrice, P. Cohen, and M. Goedert Chem. Biol. 5 1998 321
- (1998) Chem. Biol. , vol.5 , pp. 321
- Eyers, P.A.¹ Craxton, M.² Morrice, N.³ Cohen, P.⁴ Goedert, M.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.