SCOPUS 정보 검색 플랫폼

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 1, 2014, Pages 277-284

Biphenyl derivatives incorporating urea unit as novel VEGFR-2 inhibitors: Design, synthesis and biological evaluation

(7) Wang, Chen a Gao, Hongping a Dong, Jinyun a Zhang, Yanmin a Su, Ping a Shi, Yaling a Zhang, Jie a

a XI'AN JIAOTONG UNIVERSITY (China)

Author keywords

Angiogenesis; Biphenyl scaffold; Urea moiety; VEGFR 2 inhibitor

Indexed keywords

BIPHENYL DERIVATIVE; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [2 METHYL 4 (2 MORPHOLIN 4 YLETHOXY)PHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [2 METHYL 4 (2 PIPERIDIN 1 YLETHOXY)PHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [2 METHYL 4 (2 PYRROLIDIN 1 YLETHOXY)PHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [2 METHYL 4 (3 MORPHOLIN 4 YLPROPOXY)PHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [2 METHYL 5 (2 MORPHOLIN 4 YLETHOXY)PHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [2 METHYL 5 (2 PIPERIDIN 1 YLETHOXY)PHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [2 METHYL 5 (3 MORPHOLIN 4 YLPROPOXY)PHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [4 (2 MORPHOLIN 4 YLETHOXY)PHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [4 (2 PIPERIDIN 1 YLETHOXY)PHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [4 (2 PYRROLIDIN 1 YLETHOXY)PHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [4 (3 MORPHOLIN 4 YLPROPOXY)PHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [4 [2 (DIETHYLAMINO)ETHOXY] 2 METHYLPHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [4 [2 (DIETHYLAMINO)ETHOXY]PHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [4 [2 (DIMETHYLAMINO)ETHOXY] 2 METHYLPHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [4 [2 (DIMETHYLAMINO)ETHOXY] PHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [4 [3 (DIMETHYLAMINO)PROPOXY] 2 METHYLPHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [4 [3 (DIMETHYLAMINO)PROPOXY]PHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [5 [2 (DIETHYLAMINO)ETHOXY] 2 METHYLPHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [5 [2 (DIMETHYLAMINO)ETOXY] 2 METHYLPHENYL]UREA; N (4' ACETYL 3',5,6 TRIMETHOXYBIPHENYL 3 YL) N' [5 [3 (DIMETHYLAMINO)PROPOXY] 2 METHYLPHENYL]UREA; N [4 [2 (DIETHYLAMINO)ETHOXY] 2 METHYLPHENYL] N' [4' [N HYDROXYETHANIMIDOYL] 3',5,6 TRIMETHOXYBIPHENYL 3 YL]UREA; N [4 [2 (DIMETHYLAMINO)ETHOXY] 2 METHYLPHENYL] N' [4' [N HYDROXYLETHANIMIDOYL] 3',5,6 TRIMETHOXYBIPHENYL 3 YL]UREA; N [4 [3 (DIMETHYLAMINO)PROPOXY] 2 METHYLPHENYL] N' [4' [N HYDROXYETHANIMIDOYL] 3',5,6 TRIMETHOXYBIPHENYL 3 YL]UREA; N [4' [N HYDROXYETHANIMIDOYL] 3',5,6 TRIMETHOXYBIPHENYL 3 YL] N' [2 METHYL 4 (2 PIPERIDIN 1 YLETHOXY)PHENYL]UREA; SORAFENIB; SUNITINIB; UNCLASSIFIED DRUG; UNINDEXED DRUG; UREA DERIVATIVE; VASCULOTROPIN RECEPTOR 2;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL; CONTROLLED STUDY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; HUMAN; HUMAN CELL; HYDROGEN BOND; IC 50; MOLECULAR DOCKING; STRUCTURE ACTIVITY RELATION;

ANGIOGENESIS; BIPHENYL SCAFFOLD; UREA MOIETY; VEGFR-2 INHIBITOR;

BIPHENYL COMPOUNDS; CELL PROLIFERATION; HUMANS; MODELS, MOLECULAR; NEOVASCULARIZATION, PATHOLOGIC; UREA; VASCULAR ENDOTHELIAL GROWTH FACTOR RECEPTOR-2;

EID: 84891492233 PISSN: 09680896 EISSN: 14643391 Source Type: Journal
DOI: 10.1016/j.bmc.2013.11.027 Document Type: Article

Times cited : (54)

References (24)

1
- 0028929803
- J. Folkman Nat. Med. 1 1995 27
- (1995) Nat. Med. , vol.1 , pp. 27
- Folkman, J.¹

2
- 0034648765
- P. Carmeliet, and R.K. Jain Nature 407 2000 249
- (2000) Nature , vol.407 , pp. 249
- Carmeliet, P.¹ Jain, R.K.²

3
- 34249294557
- H.M. Verheul, and H.M. Pinedo Nat. Rev. Cancer 7 2007 475
- (2007) Nat. Rev. Cancer , vol.7 , pp. 475
- Verheul, H.M.¹ Pinedo, H.M.²

4
- 33750286135
- F. Bertolini, Y. Shaked, P. Mancuso, and R.S. Kerbel Nat. Rev. Drug Dis. 5 2006 835
- (2006) Nat. Rev. Drug Dis. , vol.5 , pp. 835
- Bertolini, F.¹ Shaked, Y.² Mancuso, P.³ Kerbel, R.S.⁴

5
- 33646586669
- D.H. Albert, P. Tapang, T.J. Magoc, L.J. Pease, D.R. Reuter, R.Q. Wei, J. Li, J. Guo, P.F. Bousquet, N.S. Ghoreishi-Haack, B. Wang, G.T. Bukofzer, Y.C. Wang, J.A. Stavropoulos, K. Hartandi, A.L. Niquette, N. Soni, E.F. Johnson, J.O. McCall, J.J. Bouska, Y. Luo, C.K. Donawho, Y. Dai, P.A. Marcotte, K.B. Glaser, M.R. Michaelides, and S.K. Davidsen Mol. Cancer Ther. 5 2006 995
- (2006) Mol. Cancer Ther. , vol.5 , pp. 995
- Albert, D.H.¹ Tapang, P.² Magoc, T.J.³ Pease, L.J.⁴ Reuter, D.R.⁵ Wei, R.Q.⁶ Li, J.⁷ Guo, J.⁸ Bousquet, P.F.⁹ Ghoreishi-Haack, N.S.¹⁰ Wang, B.¹¹ Bukofzer, G.T.¹² Wang, Y.C.¹³ Stavropoulos, J.A.¹⁴ Hartandi, K.¹⁵ Niquette, A.L.¹⁶ Soni, N.¹⁷ Johnson, E.F.¹⁸ McCall, J.O.¹⁹ Bouska, J.J.²⁰ more..

6
- 0032893263
- T.A. Fong, L.K. Shawver, L. Sun, C. Tang, H. App, T.J. Powell, Y.H. Kim, R. Schreck, X. Wang, W. Risau, A. Ullrich, K.P. Hirth, and G. McMahon Cancer Res. 1 1999 99
- (1999) Cancer Res. , vol.1 , pp. 99
- Fong, T.A.¹ Shawver, L.K.² Sun, L.³ Tang, C.⁴ App, H.⁵ Powell, T.J.⁶ Kim, Y.H.⁷ Schreck, R.⁸ Wang, X.⁹ Risau, W.¹⁰ Ullrich, A.¹¹ Hirth, K.P.¹² McMahon, G.¹³

7
- 33748336510
- Q.D. Nguyen, S. Rodrigues, C.M. Rodrigue, C. Rivat, C. Grijelmo, E. Bruyneel, S. Emami, S. Attoub, and C. Gespach Mol. Cancer Ther. 5 2006 2070
- (2006) Mol. Cancer Ther. , vol.5 , pp. 2070
- Nguyen, Q.D.¹ Rodrigues, S.² Rodrigue, C.M.³ Rivat, C.⁴ Grijelmo, C.⁵ Bruyneel, E.⁶ Emami, S.⁷ Attoub, S.⁸ Gespach, C.⁹

8
- 77954348591
- J. Zhang, Y. Zhang, Y. Shan, N. Li, W. Ma, and L. He Eur. J. Med. Chem. 45 2010 2798
- (2010) Eur. J. Med. Chem. , vol.45 , pp. 2798
- Zhang, J.¹ Zhang, Y.² Shan, Y.³ Li, N.⁴ Ma, W.⁵ He, L.⁶

9
- 84870557260
- Y.M. Zhang, B.L. Dai, L. Zheng, Y.Z. Zhan, J. Zhang, W.W. Smith, X.L. Wang, Y.N. Chen, and L.C. He Cell Death Dis. 3 2012 406
- (2012) Cell Death Dis. , vol.3 , pp. 406
- Zhang, Y.M.¹ Dai, B.L.² Zheng, L.³ Zhan, Y.Z.⁴ Zhang, J.⁵ Smith, W.W.⁶ Wang, X.L.⁷ Chen, Y.N.⁸ He, L.C.⁹

10
- 72549112083
- J. Zhang, Y. Zhang, S. Zhang, S. Wang, and L. He Bioorg. Med. Chem. Lett. 20 2010 718
- (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 718
- Zhang, J.¹ Zhang, Y.² Zhang, S.³ Wang, S.⁴ He, L.⁵

11
- 0034618541
- P.J. Hajduk, M. Bures, J. Praestgaard, and S.W. Fesik J. Med. Chem. 43 2000 3443
- (2000) J. Med. Chem. , vol.43 , pp. 3443
- Hajduk, P.J.¹ Bures, M.² Praestgaard, J.³ Fesik, S.W.⁴

12
- 33745298429
- Y. Liu, and N.S. Gray Nat. Chem. Biol. 2 2006 358
- (2006) Nat. Chem. Biol. , vol.2 , pp. 358
- Liu, Y.¹ Gray, N.S.²

13
- 33748423744
- J.Q. Wang, M. Gao, K.D. Miller, G.W. Sledge, and Q.H. Zheng Bioorg. Med. Chem. Lett. 16 2006 4102
- (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 4102
- Wang, J.Q.¹ Gao, M.² Miller, K.D.³ Sledge, G.W.⁴ Zheng, Q.H.⁵

14
- 84891489024
- V. Somepalli, K.P. Gopala, B.G. Mothukuri, and V.S. Gottumukkala Tetrahedron 61 2005 3013
- (2005) Tetrahedron , vol.61 , pp. 3013
- Somepalli, V.¹ Gopala, K.P.² Mothukuri, B.G.³ Gottumukkala, V.S.⁴

15
- 79956145676
- L.S. Green, L.E. Chun, A.K. Patton, X. Sun, G.J. Rosenthal, and J.P. Richards ACS Med. Chem. Lett. 2 2011 402
- (2011) ACS Med. Chem. Lett. , vol.2 , pp. 402
- Green, L.S.¹ Chun, L.E.² Patton, A.K.³ Sun, X.⁴ Rosenthal, G.J.⁵ Richards, J.P.⁶

16
- 33750434862
- J.K. Lynch, J.C. Freeman, A.S. Judd, R. Iyengar, M. Mulhern, G. Zhao, J.J. Napier, D. Wodka, S. Brodjian, B.D. Dayton, D. Falls, C. Ogiela, R.M. Reilly, T.J. Campbell, J.S. Polakowski, L. Hernandez, K.C. Marsh, R. Shapiro, V. Knourek-Segel, B. Droz, E. Bush, M. Brune, L.C. Preusser, R.M. Fryer, G.A. Reinhart, K. Houseman, G. Diaz, A. Mikhail, J.T. Limberis, H.L. Sham, C.A. Collins, and P.R. Kym J. Med. Chem. 49 2006 6569
- (2006) J. Med. Chem. , vol.49 , pp. 6569
- Lynch, J.K.¹ Freeman, J.C.² Judd, A.S.³ Iyengar, R.⁴ Mulhern, M.⁵ Zhao, G.⁶ Napier, J.J.⁷ Wodka, D.⁸ Brodjian, S.⁹ Dayton, B.D.¹⁰ Falls, D.¹¹ Ogiela, C.¹² Reilly, R.M.¹³ Campbell, T.J.¹⁴ Polakowski, J.S.¹⁵ Hernandez, L.¹⁶ Marsh, K.C.¹⁷ Shapiro, R.¹⁸ Knourek-Segel, V.¹⁹ Droz, B.²⁰ more..

17
- 3142514770
- I. Tatsuo, M. Miki, and M. Norio J. Org. Chem. 60 1995 7508
- (1995) J. Org. Chem. , vol.60 , pp. 7508
- Tatsuo, I.¹ Miki, M.² Norio, M.³

18
- 0025816845
- B.I. Alo, A. Kandil, and P.A. Patil J. Org. Chem. 56 1991 3763
- (1991) J. Org. Chem. , vol.56 , pp. 3763
- Alo, B.I.¹ Kandil, A.² Patil, P.A.³

19
- 78649671753
- E. Heiner, and A. Johann Org. Process Res. Dev. 14 2010 1501
- (2010) Org. Process Res. Dev. , vol.14 , pp. 1501
- Heiner, E.¹ Johann, A.²

20
- 33746587317
- P.A. Shawn, J.C. McWilliams, A.S. Elizabeth, R.M. Dale, D.N. Todd, and H.K. Michael Tetrahedron Lett. 47 2006 6409
- (2006) Tetrahedron Lett. , vol.47 , pp. 6409
- Shawn, P.A.¹ McWilliams, J.C.² Elizabeth, A.S.³ Dale, R.M.⁴ Todd, D.N.⁵ Michael, H.K.⁶

21
- 3843140692
- M.L. Curtin, R.R. Frey, H.R. Heyman, K.A. Sarris, D.H. Steinman, J.H. Holmes, P.F. Bousquet, G.A. Cunha, M.D. Moskey, A.A. Ahmed, L.J. Pease, K.B. Glaser, K.D. Stewart, S.K. Davidsen, and M.R. Michaelides Bioorg. Med. Chem. Lett. 14 2004 4505
- (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 4505
- Curtin, M.L.¹ Frey, R.R.² Heyman, H.R.³ Sarris, K.A.⁴ Steinman, D.H.⁵ Holmes, J.H.⁶ Bousquet, P.F.⁷ Cunha, G.A.⁸ Moskey, M.D.⁹ Ahmed, A.A.¹⁰ Pease, L.J.¹¹ Glaser, K.B.¹² Stewart, K.D.¹³ Davidsen, S.K.¹⁴ Michaelides, M.R.¹⁵

22
- 33748313108
- N.C. Becknell, A.L. Zulli, T.S. Angeles, S. Yang, M.S. Albom, L.D. Aimone, C. Robinson, H. Chang, and R.L. Hudkins Bioorg. Med. Chem. Lett. 16 2006 5368
- (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 5368
- Becknell, N.C.¹ Zulli, A.L.² Angeles, T.S.³ Yang, S.⁴ Albom, M.S.⁵ Aimone, L.D.⁶ Robinson, C.⁷ Chang, H.⁸ Hudkins, R.L.⁹

23
- 33748851665
- E.F. DiMauro, J. Newcomb, J.J. Nunes, J.E. Bemis, C. Boucher, J.L. Buchanan, W.H. Buckner, V.J. Cee, L. Chai, H.L. Deak, L.F. Epstein, T. Faust, P. Gallant, S.D. Geuns-Meyer, A. Gore, Y. Gu, B. Henkle, B.L. Hodous, F. Hsieh, X. Huang, J.L. Kim, J.H. Lee, M.W. Martin, C.E. Masse, D.C. McGowan, D. Metz, D. Mohn, K.A. Morgenstern, A. Oliveira-dos-Santos, V.F. Patel, D. Powers, P.E. Rose, S. Schneider, S.A. Tomlinson, Y.Y. Tudor, S.M. Turci, A.A. Welcher, R.D. White, H. Zhao, L. Zhu, and X. Zhu J. Med. Chem. 49 2006 5671
- (2006) J. Med. Chem. , vol.49 , pp. 5671
- Dimauro, E.F.¹ Newcomb, J.² Nunes, J.J.³ Bemis, J.E.⁴ Boucher, C.⁵ Buchanan, J.L.⁶ Buckner, W.H.⁷ Cee, V.J.⁸ Chai, L.⁹ Deak, H.L.¹⁰ Epstein, L.F.¹¹ Faust, T.¹² Gallant, P.¹³ Geuns-Meyer, S.D.¹⁴ Gore, A.¹⁵ Gu, Y.¹⁶ Henkle, B.¹⁷ Hodous, B.L.¹⁸ Hsieh, F.¹⁹ Huang, X.²⁰ more..

24
- 84866099909
- W. Lu, B. Dai, W. Ma, and Y. Zhang Oncol. Lett. 4 2012 1109
- (2012) Oncol. Lett. , vol.4 , pp. 1109
- Lu, W.¹ Dai, B.² Ma, W.³ Zhang, Y.⁴

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.