SCOPUS 정보 검색 플랫폼

Bioorganic and Medicinal Chemistry Letters

Volumn 24, Issue 15, 2014, Pages 3486-3492

Five-membered heteroaromatic ring fused-pyrimidine derivatives: Design, synthesis, and hedgehog signaling pathway inhibition study

(8) Zhang, Liandi a,b Xin, Minhang c Shen, Han b Wen, Jun b Tang, Feng b Tu, Chongxing b Zhao, Xinge b Wei, Ping a

a NANJING TECH UNIVERSITY (China)

b Jiangsu Simcere Pharmaceutical RandD Co Ltd (China)

c XI'AN JIAOTONG UNIVERSITY (China)

Author keywords

Five membered heteroaromatic ring fused pyrimidine; Hedgehog signaling pathway; Inhibitors; Synthesis

Indexed keywords

FUSED HETEROCYCLIC RINGS; PROTEIN INHIBITOR; PURINE DERIVATIVE; PYRIMIDINE DERIVATIVE; PYRROLO[2,3 D]PYRIMIDINE DERIVATIVE; PYRROLO[3,2 D]PYRIMIDINE DERIVATIVE; SONIC HEDGEHOG PROTEIN; THIENO[2,3 D]PYRIMIDINE DERIVATIVE; THIENO[3,2 D]PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; VISMODEGIB; FURO[3,2 D]PYRIMIDINE DERIVATIVE; PYRIMIDINE;

ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; LIPOPHILICITY; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION; ANIMAL; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; METABOLISM; SYNTHESIS;

ERINACEIDAE;

ANIMALS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; HEDGEHOG PROTEINS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MOLECULAR STRUCTURE; PYRIMIDINES; SIGNAL TRANSDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84904060981 PISSN: 0960894X EISSN: 14643405 Source Type: Journal
DOI: 10.1016/j.bmcl.2014.05.066 Document Type: Article

Times cited : (23)

References (33)

1
- 0035822098
- X. Zeng, J.A. Goetz, L.M. Suber, W.J. Scott Jr., C.M. Schreiner, and D.J. Robbins Nature 411 2001 716
- (2001) Nature , vol.411 , pp. 716
- Zeng, X.¹ Goetz, J.A.² Suber, L.M.³ Scott, Jr.W.J.⁴ Schreiner, C.M.⁵ Robbins, D.J.⁶

2
- 63149124772
- H. Tian, C.A. Callahan, K.J. DuPree, W.C. Darbonne, C.P. Ahn, S.J. Scales, and F. Sauvage Proc. Natl. Acad. Sci. U.S.A. 106 2009 4254
- (2009) Proc. Natl. Acad. Sci. U.S.A. , vol.106 , pp. 4254
- Tian, H.¹ Callahan, C.A.² Dupree, K.J.³ Darbonne, W.C.⁴ Ahn, C.P.⁵ Scales, S.J.⁶ Sauvage, F.⁷

3
- 84855888693
- H. Onishi, and M. Katano Cancer Sci. 102 2011 1756
- (2011) Cancer Sci. , vol.102 , pp. 1756
- Onishi, H.¹ Katano, M.²

4
- 0011102935
- D.M. Stone, M. Hynes, M. Armanini, T.A. Swanson, Q. Gu, R.L. Johnson, M.P. Scott, D. Pennica, A. Goddard, H. Phillips, M. Noll, J.E. Hooper, F. Sauvage, and A. Rosenthal Nature 384 1996 129
- (1996) Nature , vol.384 , pp. 129
- Stone, D.M.¹ Hynes, M.² Armanini, M.³ Swanson, T.A.⁴ Gu, Q.⁵ Johnson, R.L.⁶ Scott, M.P.⁷ Pennica, D.⁸ Goddard, A.⁹ Phillips, H.¹⁰ Noll, M.¹¹ Hooper, J.E.¹² Sauvage, F.¹³ Rosenthal, A.¹⁴

5
- 80955181031
- J.M. Ng, and T. Curran Nat. Rev. Cancer 11 2011 493
- (2011) Nat. Rev. Cancer , vol.11 , pp. 493
- Ng, J.M.¹ Curran, T.²

6
- 79960935826
- C. Metcalfe, and F.J. de Sauvage Cancer Res. 71 2011 5057
- (2011) Cancer Res. , vol.71 , pp. 5057
- Metcalfe, C.¹ De Sauvage, F.J.²

7
- 84874059433
- M.K. Hadden Expert Opin. Ther. Patents 23 2013 345
- (2013) Expert Opin. Ther. Patents , vol.23 , pp. 345
- Hadden, M.K.¹

8
- 84862907616
- Y. Li, M.Y. Maitah, A. Ahmad, D. Kong, B. Bao, and F.H. Sarkar Expert Opin. Ther. Patents 16 2012 49
- (2012) Expert Opin. Ther. Patents , vol.16 , pp. 49
- Li, Y.¹ Maitah, M.Y.² Ahmad, A.³ Kong, D.⁴ Bao, B.⁵ Sarkar, F.H.⁶

9
- 33751549095
- L.L. Rubin, and F.J. de Sauvage Nat. Rev. Drug Disc. 5 2006 1026
- (2006) Nat. Rev. Drug Disc. , vol.5 , pp. 1026
- Rubin, L.L.¹ De Sauvage, F.J.²

10
- 84878643242
- J. Ruch, and E. Kim Drugs 73 2013 613
- (2013) Drugs , vol.73 , pp. 613
- Ruch, J.¹ Kim, E.²

11
- 70350496540
- R. Yauch, G. Dijkgraaf, B. Alicke, T. Januario, C. Ahn, T. Holcomb, K. Pujara, J. Stinson, C. Callahan, T. Tang, J. Bazan, Z. Kan, S. Seshagiri, C. Hann, S. Gould, J. Low, C. Rudin, and F. Sauvage Science 326 2009 572
- (2009) Science , vol.326 , pp. 572
- Yauch, R.¹ Dijkgraaf, G.² Alicke, B.³ Januario, T.⁴ Ahn, C.⁵ Holcomb, T.⁶ Pujara, K.⁷ Stinson, J.⁸ Callahan, C.⁹ Tang, T.¹⁰ Bazan, J.¹¹ Kan, Z.¹² Seshagiri, S.¹³ Hann, C.¹⁴ Gould, S.¹⁵ Low, J.¹⁶ Rudin, C.¹⁷ Sauvage, F.¹⁸

12
- 84866234204
- T. Ohashi, Y. Oguro, T. Tanaka, Z. Shiokawa, Y. Tanaka, S. Shibata, Y. Sato, H. Yamakawa, H. Hattori, Y. Yamamoto, S. Kondo, M. Miyamoto, M. Nishihara, Y. Ishimura, H. Tojo, A. Baba, and S. Sasaki Bioorg. Med. Chem. 20 2012 5507
- (2012) Bioorg. Med. Chem. , vol.20 , pp. 5507
- Ohashi, T.¹ Oguro, Y.² Tanaka, T.³ Shiokawa, Z.⁴ Tanaka, Y.⁵ Shibata, S.⁶ Sato, Y.⁷ Yamakawa, H.⁸ Hattori, H.⁹ Yamamoto, Y.¹⁰ Kondo, S.¹¹ Miyamoto, M.¹² Nishihara, M.¹³ Ishimura, Y.¹⁴ Tojo, H.¹⁵ Baba, A.¹⁶ Sasaki, S.¹⁷

13
- 69949084378
- K.D. Robarge, S.A. Brunton, G.M. Castanedo, Y. Cui, M.S. Dina, R. Goldsmith, S.E. Gould, O. Guichert, J.L. Gunzner, J. Halladay, W. Jia, C. Khojasteh, M.F. Koehler, K. Kotkow, H. La, R.L. Lalonde, K. Lau, L. Lee, D. Marshall, J.C. Marsters Jr., L.J. Murray, C. Qian, L.L. Rubin, L. Salphati, M.S. Stanley, J.H. Stibbard, D.P. Sutherlin, S. Ubhayaker, S. Wang, S. Wong, and M. Xie Bioorg. Med. Chem. Lett. 19 2009 5576
- (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 5576
- Robarge, K.D.¹ Brunton, S.A.² Castanedo, G.M.³ Cui, Y.⁴ Dina, M.S.⁵ Goldsmith, R.⁶ Gould, S.E.⁷ Guichert, O.⁸ Gunzner, J.L.⁹ Halladay, J.¹⁰ Jia, W.¹¹ Khojasteh, C.¹² Koehler, M.F.¹³ Kotkow, K.¹⁴ La, H.¹⁵ Lalonde, R.L.¹⁶ Lau, K.¹⁷ Lee, L.¹⁸ Marshall, D.¹⁹ Marsters, Jr.J.C.²⁰ more..

14
- 84863172647
- M.J. Munchhof, Q. Li, A. Shavnya, G.V. Borzillo, T.L. Boyden, C.S. Jones, S.D. LaGreca, L. Martinez-Alsina, N. Patel, K. Pelletier, L.A. Reiter, M.D. Robbins, and G.T. Tkalcevic ACS Med. Chem. Lett. 3 2012 106
- (2012) ACS Med. Chem. Lett. , vol.3 , pp. 106
- Munchhof, M.J.¹ Li, Q.² Shavnya, A.³ Borzillo, G.V.⁴ Boyden, T.L.⁵ Jones, C.S.⁶ Lagreca, S.D.⁷ Martinez-Alsina, L.⁸ Patel, N.⁹ Pelletier, K.¹⁰ Reiter, L.A.¹¹ Robbins, M.D.¹² Tkalcevic, G.T.¹³

15
- 84881030230
- S. Peukert, F. He, M. Dai, R. Zhang, Y. Sun, K. Miller-Mislin, M. McEwan, B. Lagu, K. Wang, N. Yusuff, A. Bourret, A. Ramamurthy, A. Vattay, A. Wang, R. Guo, J. Yuan, J. Green, J. Williams, S. Buonamici, J.F. Kelleher, and M. Dorsch ChemMedChem 8 2013 1261
- (2013) ChemMedChem , vol.8 , pp. 1261
- Peukert, S.¹ He, F.² Dai, M.³ Zhang, R.⁴ Sun, Y.⁵ Miller-Mislin, K.⁶ McEwan, M.⁷ Lagu, B.⁸ Wang, K.⁹ Yusuff, N.¹⁰ Bourret, A.¹¹ Ramamurthy, A.¹² Vattay, A.¹³ Wang, A.¹⁴ Guo, R.¹⁵ Yuan, J.¹⁶ Green, J.¹⁷ Williams, J.¹⁸ Buonamici, S.¹⁹ Kelleher, J.F.²⁰ Dorsch, M.²¹ more..

16
- 57749098407
- S. Peukert, R.K. Jain, A. Geisser, Y. Sun, R. Zhang, A. Bourret, A. Carlson, J. Dasilva, A. Ramamurthy, and J.F. Kelleher Bioorg. Med. Chem. Lett. 19 2009 328
- (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 328
- Peukert, S.¹ Jain, R.K.² Geisser, A.³ Sun, Y.⁴ Zhang, R.⁵ Bourret, A.⁶ Carlson, A.⁷ Dasilva, J.⁸ Ramamurthy, A.⁹ Kelleher, J.F.¹⁰

17
- 80051921468
- E. Muraglia, J.M. Ontoria, D. Branca, G. Dessole, A. Bresciani, M. Fonsi, C. Giuliano, L. Llauger Bufi, E. Monteagudo, M.C. Palumbi, C. Torrisi, M. Rowley, C. Steinkühler, and P. Jones Bioorg. Med. Chem. Lett. 21 2011 5283
- (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 5283
- Muraglia, E.¹ Ontoria, J.M.² Branca, D.³ Dessole, G.⁴ Bresciani, A.⁵ Fonsi, M.⁶ Giuliano, C.⁷ Llauger Bufi, L.⁸ Monteagudo, E.⁹ Palumbi, M.C.¹⁰ Torrisi, C.¹¹ Rowley, M.¹² Steinkühler, C.¹³ Jones, P.¹⁴

18
- 81155159749
- M.L. Brown, W. Aaron, R.J. Austin, A. Chong, T. Huang, B. Jiang, J.A. Kaizerman, G. Lee, B.S. Lucas, D.L. McMinn, J. Orf, M. Rong, M.M. Toteva, G. Xu, Q. Ye, W. Zhong, M.R. Degraffenreid, D. Wickramasinghe, J.P. Powers, R. Hungate, and M.G. Johnson Bioorg. Med. Chem. Lett. 21 2011 5206
- (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 5206
- Brown, M.L.¹ Aaron, W.² Austin, R.J.³ Chong, A.⁴ Huang, T.⁵ Jiang, B.⁶ Kaizerman, J.A.⁷ Lee, G.⁸ Lucas, B.S.⁹ McMinn, D.L.¹⁰ Orf, J.¹¹ Rong, M.¹² Toteva, M.M.¹³ Xu, G.¹⁴ Ye, Q.¹⁵ Zhong, W.¹⁶ Degraffenreid, M.R.¹⁷ Wickramasinghe, D.¹⁸ Powers, J.P.¹⁹ Hungate, R.²⁰ Johnson, M.G.²¹ more..

19
- 79957922542
- G. Guerlet, T. Spangenberg, A. Mann, H. Faure, and M. Ruat Bioorg. Med. Chem. Lett. 21 2011 3608
- (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 3608
- Guerlet, G.¹ Spangenberg, T.² Mann, A.³ Faure, H.⁴ Ruat, M.⁵

20
- 84867848829
- J. Wang, R.A. Mook Jr., J. Lu, D.M. Gooden, A. Ribeiro, A. Guo, L.S. Barak, H.K. Lyerly, and W. Chen Bioorg. Med. Chem. 20 2012 6751
- (2012) Bioorg. Med. Chem. , vol.20 , pp. 6751
- Wang, J.¹ Mook, Jr.R.A.² Lu, J.³ Gooden, D.M.⁴ Ribeiro, A.⁵ Guo, A.⁶ Barak, L.S.⁷ Lyerly, H.K.⁸ Chen, W.⁹

21
- 80051942180
- J.M. Ontoria, L.L. Bufi, C. Torrisi, A. Bresciani, C. Giomini, M. Rowley, S. Serafini, H. Bin, W. Hao, C. Steinkühler, and P. Jones Bioorg. Med. Chem. Lett. 21 2011 5274
- (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 5274
- Ontoria, J.M.¹ Bufi, L.L.² Torrisi, C.³ Bresciani, A.⁴ Giomini, C.⁵ Rowley, M.⁶ Serafini, S.⁷ Bin, H.⁸ Hao, W.⁹ Steinkühler, C.¹⁰ Jones, P.¹¹

22
- 79960351998
- S. Malancona, S. Altamura, G. Filocamo, O. Kinzel, J.I. Hernando, M. Rowley, R. Scarpelli, C. Steinkühler, and P. Jones Bioorg. Med. Chem. Lett. 21 2011 4422
- (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 4422
- Malancona, S.¹ Altamura, S.² Filocamo, G.³ Kinzel, O.⁴ Hernando, J.I.⁵ Rowley, M.⁶ Scarpelli, R.⁷ Steinkühler, C.⁸ Jones, P.⁹

23
- 79960349060
- O. Kinzel, A. Alfieri, S. Altamura, M. Brunetti, S. Bufali, F. Colaceci, F. Ferrigno, G. Filocamo, M. Fonsi, P. Gallinari, S. Malancona, J.I. Hernando, E. Monteagudo, M.V. Orsale, M.C. Palumbi, V. Pucci, M. Rowley, R. Sasso, R. Scarpelli, C. Steinkühler, and P. Jones Bioorg. Med. Chem. Lett. 21 2011 4429
- (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 4429
- Kinzel, O.¹ Alfieri, A.² Altamura, S.³ Brunetti, M.⁴ Bufali, S.⁵ Colaceci, F.⁶ Ferrigno, F.⁷ Filocamo, G.⁸ Fonsi, M.⁹ Gallinari, P.¹⁰ Malancona, S.¹¹ Hernando, J.I.¹² Monteagudo, E.¹³ Orsale, M.V.¹⁴ Palumbi, M.C.¹⁵ Pucci, V.¹⁶ Rowley, M.¹⁷ Sasso, R.¹⁸ Scarpelli, R.¹⁹ Steinkühler, C.²⁰ Jones, P.²¹ more..

24
- 67649983452
- N. Mahindroo, C. Punchihewa, and N. Fujii J. Med. Chem. 52 2009 3829
- (2009) J. Med. Chem. , vol.52 , pp. 3829
- Mahindroo, N.¹ Punchihewa, C.² Fujii, N.³

25
- 78651250889
- B. Fink, D. Norris, H. Mastalerz, P. Chen, B. Goyal, Y. Zhao, S. Kim, G. Vite, F. Lee, H. Zhang, S. Oppenheimer, J. Tokarski, T. Wong, and A. Gavai Bioorg. Med. Chem. Lett. 21 2011 781
- (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 781
- Fink, B.¹ Norris, D.² Mastalerz, H.³ Chen, P.⁴ Goyal, B.⁵ Zhao, Y.⁶ Kim, S.⁷ Vite, G.⁸ Lee, F.⁹ Zhang, H.¹⁰ Oppenheimer, S.¹¹ Tokarski, J.¹² Wong, T.¹³ Gavai, A.¹⁴

26
- 84866246074
- T. Ohashi, Y. Oguro, T. Tanaka, Z. Shiokawa, S. Shibata, Y. Sato, H. Yamakawa, H. Hattori, Y. Yamamoto, S. Kondo, M. Miyamoto, H. Tojo, A. Baba, and S. Sasaki Bioorg. Med. Chem. 20 2012 5496
- (2012) Bioorg. Med. Chem. , vol.20 , pp. 5496
- Ohashi, T.¹ Oguro, Y.² Tanaka, T.³ Shiokawa, Z.⁴ Shibata, S.⁵ Sato, Y.⁶ Yamakawa, H.⁷ Hattori, H.⁸ Yamamoto, Y.⁹ Kondo, S.¹⁰ Miyamoto, M.¹¹ Tojo, H.¹² Baba, A.¹³ Sasaki, S.¹⁴

27
- 84861903142
- A. Dlugosz, S. Agrawal, and P. Kirkpatrick Nat. Rev. Drug Disc. 11 2012 437
- (2012) Nat. Rev. Drug Disc. , vol.11 , pp. 437
- Dlugosz, A.¹ Agrawal, S.² Kirkpatrick, P.³

28
- 77956292749
- W. Pan, X. Wu, J. Jiang, W. Gao, Y. Wan, D. Cheng, D. Han, J. Liu, N.P. Englund, Y. Wang, S. Peukert, K. Miller-Moslin, J. Yaun, R. Guo, M. Matsumoto, A. Vattay, Y. Jiang, J. Tsao, S. Fangxian, A.C. Pferdekamper, S. Dodd, T. Tuntland, M. Wieslawa, J.F. Kelleher, Y. Yao, M. Warmuth, J. Williams, and M. Dorsch ACS Med. Chem. Lett. 1 2010 130
- (2010) ACS Med. Chem. Lett. , vol.1 , pp. 130
- Pan, W.¹ Wu, X.² Jiang, J.³ Gao, W.⁴ Wan, Y.⁵ Cheng, D.⁶ Han, D.⁷ Liu, J.⁸ Englund, N.P.⁹ Wang, Y.¹⁰ Peukert, S.¹¹ Miller-Moslin, K.¹² Yaun, J.¹³ Guo, R.¹⁴ Matsumoto, M.¹⁵ Vattay, A.¹⁶ Jiang, Y.¹⁷ Tsao, J.¹⁸ Fangxian, S.¹⁹ Pferdekamper, A.C.²⁰ more..

29
- 84888868222
- M. Xin, J. Wen, F. Tang, C. Tu, H. Shen, and X. Zhao Bioorg. Med. Chem. Lett. 23 2013 6777
- (2013) Bioorg. Med. Chem. Lett. , vol.23 , pp. 6777
- Xin, M.¹ Wen, J.² Tang, F.³ Tu, C.⁴ Shen, H.⁵ Zhao, X.⁶

30
- 84893650738
- M. Xin, J. Wen, F. Tang, C. Tu, W. Huang, H. Shen, X. Zhao, L. Cheng, M. Wang, and L. Zhang Bioorg. Med. Chem. Lett. 24 2014 983
- (2014) Bioorg. Med. Chem. Lett. , vol.24 , pp. 983
- Xin, M.¹ Wen, J.² Tang, F.³ Tu, C.⁴ Huang, W.⁵ Shen, H.⁶ Zhao, X.⁷ Cheng, L.⁸ Wang, M.⁹ Zhang, L.¹⁰

31
- 84904050168
- 10.6023/cjoc201401004 (published online)
- L. Zhang, M. Xin, J. Wen, F. Tang, C. Tu, H. Shen, and P. Wei Chin. J. Org. Chem. 2014 10.6023/cjoc201401004 (published online)
- (2014) Chin. J. Org. Chem.
- Zhang, L.¹ Xin, M.² Wen, J.³ Tang, F.⁴ Tu, C.⁵ Shen, H.⁶ Wei, P.⁷

32
- 84893729197
- M. Xin, L. Zhang, F. Tang, C. Tu, J. Wen, X. Zhao, Z. Liu, L. Cheng, and H. Shen Bioorg. Med. Chem. 24 2014 1429
- (2014) Bioorg. Med. Chem. , vol.24 , pp. 1429
- Xin, M.¹ Zhang, L.² Tang, F.³ Tu, C.⁴ Wen, J.⁵ Zhao, X.⁶ Liu, Z.⁷ Cheng, L.⁸ Shen, H.⁹

33
- 84904429186
- 10.1007/s00044-014-0959-3 (published online)
- M. Xin, L. Zhang, H. Shen, J. Wen, C. Tu, Z. Liu, L. Cheng, and X. Zhao Med. Chem. Res. 2014 10.1007/s00044-014-0959-3 (published online)
- (2014) Med. Chem. Res.
- Xin, M.¹ Zhang, L.² Shen, H.³ Wen, J.⁴ Tu, C.⁵ Liu, Z.⁶ Cheng, L.⁷ Zhao, X.⁸

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.