SCOPUS 정보 검색 플랫폼

Tetrahedron

Volumn 67, Issue 52, 2011, Pages 10261-10266

Design, synthesis, and biological evaluation of estrone-derived hedgehog signaling inhibitors

(5) Winkler, Jeffrey D a Isaacs, André K a Xiang, Chaomei b Baubet, Valérie b Dahmane, Nadia b

a UNIVERSITY OF PENNSYLVANIA (United States)

b WISTAR INSTITUTE (United States)

Author keywords

Cancer chemotherapy; Cyclopamine; Hedgehog signaling; Steroidal alkaloid; Structure activity relationships

Indexed keywords

1' [(3 BROMOPYRIDIN 2 YL)METHYL] 7A' METHYL 1',2',3',6',7',7A' HEXAHYDROSPIRO([1,3]DITHIOLANE 2,5' INDEN) 1' OL; 4 [7A' METHYL 2',6',7',7A' TETRAHYDRO 3H SPIRO(FURO[3,2 B]PYRIDINE 2,1' INDEN) 5' YL]PHENOL; 7A' METHYL 2',3',7',7A' TETRAHYDRO 3H SPIRO(FURO[3,2 B]PYRIDINE 2,1' INDEN) 5'(6'H) ONE; 7A' METHYL 2',6',7',7A' TETRAHYDRO 3H SPIRO(FURO[3,2 B]PYRIDINE 2,1' INDEN) 5' YL TRIFLUOROMETHANESULFONATE; 7A' METHYL 5' PHENYL 2',6',7',7A' TETRAHYDRO 3H SPIRO(FURO[3,2 B]PYRIDINE 2,1' INDENE); ANTINEOPLASTIC AGENT; CYCLOPAMINE; CYCLOPAMINE DERIVATIVE; ESTRONE DERIVATIVE; IPI 926; PROTEIN INHIBITOR; SONIC HEDGEHOG PROTEIN; UNCLASSIFIED DRUG; VISMODEGIB;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL VIABILITY; CHEMICAL MODIFICATION; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; PHARMACOPHORE; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; TECHNIQUE;

ERINACEIDAE;

EID: 82255179076 PISSN: 00404020 EISSN: 14645416 Source Type: Journal
DOI: 10.1016/j.tet.2011.10.028 Document Type: Article

Times cited : (8)

References (43)

1
- 0014353359
- W. Binns, L.F. James, R.F. Keeler, and L.D. Balls Cancer Res. 28 1968 2323 2326
- (1968) Cancer Res. , vol.28 , pp. 2323-2326
- Binns, W.¹ James, L.F.² Keeler, R.F.³ Balls, L.D.⁴

2
- 0013921746
- R.F. Keeler, and W. Binns Can. J. Biochem. 44 1966 829 838
- (1966) Can. J. Biochem. , vol.44 , pp. 829-838
- Keeler, R.F.¹ Binns, W.²

3
- 0032486433
- M.K. Cooper, J.A. Porter, K.E. Young, and P.A. Beachy Science 280 1998 1603 1607
- (1998) Science , vol.280 , pp. 1603-1607
- Cooper, M.K.¹ Porter, J.A.² Young, K.E.³ Beachy, P.A.⁴

4
- 0031723219
- J.P. Incardona, W. Gaffield, R.P. Kapur, and H. Roelink Development 125 1998 3553 3562
- (1998) Development , vol.125 , pp. 3553-3562
- Incardona, J.P.¹ Gaffield, W.² Kapur, R.P.³ Roelink, H.⁴

5
- 17144431776
- J.E. Hooper, and M.P. Scott Nat. Rev. Mol. Cell Biol. 6 2005 306 317
- (2005) Nat. Rev. Mol. Cell Biol. , vol.6 , pp. 306-317
- Hooper, J.E.¹ Scott, M.P.²

6
- 0035577854
- P.W. Ingham, and A.P. McMahon Genes Dev. 15 2001 3059 3087
- (2001) Genes Dev. , vol.15 , pp. 3059-3087
- Ingham, P.W.¹ McMahon, A.P.²

7
- 0036829397
- J.K. Chen, J. Taipale, M.K. Cooper, and P.A. Beachy Genes Dev. 16 2002 2743 2748
- (2002) Genes Dev. , vol.16 , pp. 2743-2748
- Chen, J.K.¹ Taipale, J.² Cooper, M.K.³ Beachy, P.A.⁴

8
- 15844386165
- J. Hahn, C. Wicking, P. Zaphiropoulous, M. Gailini, S. Shanley, A. Chidambaram, I. Vorechovsky, E. Holmberg, A. Unden, S. Gillies, K. Negus, I. Smyth, C. Pressman, D. Leffell, B. Gerrard, A. Goldstein, M. Dean, R. Toftgard, G. Chenevix-Trench, B. Wainwright, and A. Bale Cell 85 1996 841 851
- (1996) Cell , vol.85 , pp. 841-851
- Hahn, J.¹ Wicking, C.² Zaphiropoulous, P.³ Gailini, M.⁴ Shanley, S.⁵ Chidambaram, A.⁶ Vorechovsky, I.⁷ Holmberg, E.⁸ Unden, A.⁹ Gillies, S.¹⁰ Negus, K.¹¹ Smyth, I.¹² Pressman, C.¹³ Leffell, D.¹⁴ Gerrard, B.¹⁵ Goldstein, A.¹⁶ Dean, M.¹⁷ Toftgard, R.¹⁸ Chenevix-Trench, G.¹⁹ Wainwright, B.²⁰ Bale, A.²¹ more..

9
- 15844381336
- R. Johnson, A. Rothman, J. Xie, L. Goodrich, J. Bare, J. Bonifas, A. Quinn, R. Myers, D. Cox, E. Epstein, and M. Scott Science 272 1996 1668 1671
- (1996) Science , vol.272 , pp. 1668-1671
- Johnson, R.¹ Rothman, A.² Xie, J.³ Goodrich, L.⁴ Bare, J.⁵ Bonifas, J.⁶ Quinn, A.⁷ Myers, R.⁸ Cox, D.⁹ Epstein, E.¹⁰ Scott, M.¹¹

10
- 0030844141
- N. Dahmane, J. Lee, P. Robbins, P. Heller, and A. Ruiz i Altaba Nature 389 1997 876 881
- (1997) Nature , vol.389 , pp. 876-881
- Dahmane, N.¹ Lee, J.² Robbins, P.³ Heller, P.⁴ Ruiz Altaba I, A.⁵

11
- 82255166615
- http://www.dungevalley.co.uk.

12
- 82255180392
- http://externalities.tumblr.com/post/162704398/cyclopia.

13
- 0037200078
- D. Berman, S. Karhadkar, A. Hallahan, J. Pritchard, C. Eberhart, D. Watkins, J. Chen, J. Taipale, J. Olson, and P. Beachy Science 297 2002 1559 1561
- (2002) Science , vol.297 , pp. 1559-1561
- Berman, D.¹ Karhadkar, S.² Hallahan, A.³ Pritchard, J.⁴ Eberhart, C.⁵ Watkins, D.⁶ Chen, J.⁷ Taipale, J.⁸ Olson, J.⁹ Beachy, P.¹⁰

14
- 33846237601
- V. Clement, P. Sanchez, N. de Tribolet, I. Radovanovic, and A. Ruiz i Altaba Curr. Biol. 17 2007 165 172
- (2007) Curr. Biol. , vol.17 , pp. 165-172
- Clement, V.¹ Sanchez, P.² De Tribolet, N.³ Radovanovic, I.⁴ Ruiz Altaba I, A.⁵

15
- 0035691884
- N. Dahmane, P. Sanchez, Y. Gitton, V. Palma, T. Sun, M. Beyna, H. Weiner, and A. Ruiz i Altaba Development 128 2001 5201 5212
- (2001) Development , vol.128 , pp. 5201-5212
- Dahmane, N.¹ Sanchez, P.² Gitton, Y.³ Palma, V.⁴ Sun, T.⁵ Beyna, M.⁶ Weiner, H.⁷ Ruiz Altaba I, A.⁸

16
- 34347226348
- B. Stecca, C. Mas, V. Clement, M. Zbinden, R. Correa, V. Piguet, F. Beermann, and A. Ruiz Proc. Natl. Acad. Sci. U.S.A. 104 2007 5895 5900
- (2007) Proc. Natl. Acad. Sci. U.S.A. , vol.104 , pp. 5895-5900
- Stecca, B.¹ Mas, C.² Clement, V.³ Zbinden, M.⁴ Correa, R.⁵ Piguet, V.⁶ Beermann, F.⁷ Ruiz, A.⁸

17
- 33847022189
- Z. Yuan, J. Goetz, S. Singh, S. Ogden, W. Petty, C. Black, V. Memoli, E. Dmitrovsky, and D. Robbins Oncogene 26 2007 1046 1055
- (2007) Oncogene , vol.26 , pp. 1046-1055
- Yuan, Z.¹ Goetz, J.² Singh, S.³ Ogden, S.⁴ Petty, W.⁵ Black, C.⁶ Memoli, V.⁷ Dmitrovsky, E.⁸ Robbins, D.⁹

18
- 6044243650
- S. Karhadkar, G. Bova, N. Abdallah, S. Dhara, D. Gardner, A. Maitra, J. Isaacs, D. Berman, and P. Beachy Nature 431 2004 707 712
- (2004) Nature , vol.431 , pp. 707-712
- Karhadkar, S.¹ Bova, G.² Abdallah, N.³ Dhara, S.⁴ Gardner, D.⁵ Maitra, A.⁶ Isaacs, J.⁷ Berman, D.⁸ Beachy, P.⁹

19
- 4344659678
- P. Sanchez, A. Hernandez, B. Stecca, A. Kahler, A. DeBueme, A. Barrett, M. Beyna, M. Datta, S. Datta, and A. Ruiz Proc. Natl. Acad. Sci. U.S.A. 101 2004 12561 12566
- (2004) Proc. Natl. Acad. Sci. U.S.A. , vol.101 , pp. 12561-12566
- Sanchez, P.¹ Hernandez, A.² Stecca, B.³ Kahler, A.⁴ Debueme, A.⁵ Barrett, A.⁶ Beyna, M.⁷ Datta, M.⁸ Datta, S.⁹ Ruiz, A.¹⁰

20
- 13644261744
- T. Sheng, C. Li, X. Zhang, S. Chi, N. He, K. Chen, F. McCormick, Z. Gatalica, and J. Xie Mol. Cancer 3 2004 29
- (2004) Mol. Cancer , vol.3 , pp. 29
- Sheng, T.¹ Li, C.² Zhang, X.³ Chi, S.⁴ He, N.⁵ Chen, K.⁶ McCormick, F.⁷ Gatalica, Z.⁸ Xie, J.⁹

21
- 0242669237
- D. Watkins, D. Berman, S. Burkholder, B. Wang, P. Beachy, and S. Baylin Nature 422 2003 313 317
- (2003) Nature , vol.422 , pp. 313-317
- Watkins, D.¹ Berman, D.² Burkholder, S.³ Wang, B.⁴ Beachy, P.⁵ Baylin, S.⁶

22
- 0242268525
- D. Berman, S. Karhadkar, A. Maitra, D. Montes, M. Gerstenblith, K. Briggs, A. Parker, Y. Shimada, J. Eshleman, D. Watkins, and P. Beachy Nature 425 2003 846 851
- (2003) Nature , vol.425 , pp. 846-851
- Berman, D.¹ Karhadkar, S.² Maitra, A.³ Montes, D.⁴ Gerstenblith, M.⁵ Briggs, K.⁶ Parker, A.⁷ Shimada, Y.⁸ Eshleman, J.⁹ Watkins, D.¹⁰ Beachy, P.¹¹

23
- 12344301234
- P. Sanchez, and A. Ruiz i Altaba Mech. Dev. 122 2005 223 230
- (2005) Mech. Dev. , vol.122 , pp. 223-230
- Sanchez, P.¹ Ruiz Altaba I, A.²

24
- 79959384320
- For recent SAR on cyclopamine-derived structures, see: P. Heretsch, A. Buttner, L. Tzagkaroulaki, S. Zahn, B. Kirchner, and A. Giannis Chem. Commun. 2011 7362 7364
- (2011) Chem. Commun. , pp. 7362-7364
- Heretsch, P.¹ Buttner, A.² Tzagkaroulaki, L.³ Zahn, S.⁴ Kirchner, B.⁵ Giannis, A.⁶

25
- 56249121238
- M. Tremblay, M. Nevalainen, S. Nair, J. Porter, A. Castro, M. Behnke, L. Yu, M. Hagel, K. White, K. Faia, L. Grenier, M. Campbell, J. Cushing, C. Woodward, J. Hoyt, M. Foley, M. Read, J. Sydor, J. Tong, V. Palombella, K. McGovern, and J. Adams J. Med. Chem. 51 2008 6646 6649
- (2008) J. Med. Chem. , vol.51 , pp. 6646-6649
- Tremblay, M.¹ Nevalainen, M.² Nair, S.³ Porter, J.⁴ Castro, A.⁵ Behnke, M.⁶ Yu, L.⁷ Hagel, M.⁸ White, K.⁹ Faia, K.¹⁰ Grenier, L.¹¹ Campbell, M.¹² Cushing, J.¹³ Woodward, C.¹⁴ Hoyt, J.¹⁵ Foley, M.¹⁶ Read, M.¹⁷ Sydor, J.¹⁸ Tong, J.¹⁹ Palombella, V.²⁰ McGovern, K.²¹ Adams, J.²² more..

26
- 79960061444
- For a general discussion, see
- For a general discussion, see E. Dolgin Nat. Med. 17 2011 523
- (2011) Nat. Med. , vol.17 , pp. 523
- Dolgin, E.¹

27
- 0014786872
- R.F. Keeler Teratology 3 1970 169 173
- (1970) Teratology , vol.3 , pp. 169-173
- Keeler, R.F.¹

28
- 77950858208
- S. Wilson, M. Strand, A. Krapp, F. Rise, D. Petersen, and S. Krauss J. Pharm. Biomed. Anal. 52 2010 707 713
- (2010) J. Pharm. Biomed. Anal. , vol.52 , pp. 707-713
- Wilson, S.¹ Strand, M.² Krapp, A.³ Rise, F.⁴ Petersen, D.⁵ Krauss, S.⁶

29
- 0026092559
- R. Nagata, and K. Izumi Jpn. J. Pharmacol. 55 1991 129 137
- (1991) Jpn. J. Pharmacol. , vol.55 , pp. 129-137
- Nagata, R.¹ Izumi, K.²

30
- 0032890406
- C.D. Thron, and F.V. McCann Gen. Pharmacol. 32 1998 81 89
- (1998) Gen. Pharmacol. , vol.32 , pp. 81-89
- Thron, C.D.¹ McCann, F.V.²

31
- 67650723106
- M. Tremblay, A. Lescarbeau, M. Grogan, E. Tan, G. Lin, B. Austad, L. Yu, M. Behnke, S. Nair, M. Hagel, K. White, J. Conley, J. Manna, T. Alvarez-Diez, J. Hoyt, C. Woodward, J. Sydor, M. Pink, J. MacDougall, M. Campbell, J. Cushing, J. Ferguson, M. Curtis, K. McGovern, M. Read, V. Palombella, J. Adams, and A. Castro J. Med. Chem. 52 2009 4400 4418
- (2009) J. Med. Chem. , vol.52 , pp. 4400-4418
- Tremblay, M.¹ Lescarbeau, A.² Grogan, M.³ Tan, E.⁴ Lin, G.⁵ Austad, B.⁶ Yu, L.⁷ Behnke, M.⁸ Nair, S.⁹ Hagel, M.¹⁰ White, K.¹¹ Conley, J.¹² Manna, J.¹³ Alvarez-Diez, T.¹⁴ Hoyt, J.¹⁵ Woodward, C.¹⁶ Sydor, J.¹⁷ Pink, M.¹⁸ MacDougall, J.¹⁹ Campbell, M.²⁰ more..

32
- 0037195074
- J. Chen, J. Taipale, K. Young, T. Maiti, and P. Beachy Proc. Natl. Acad. Sci. U.S.A. 99 2002 14071 14076
- (2002) Proc. Natl. Acad. Sci. U.S.A. , vol.99 , pp. 14071-14076
- Chen, J.¹ Taipale, J.² Young, K.³ Maiti, T.⁴ Beachy, P.⁵

33
- 18644368453
- M. Frank-Kamenetsky, X. Zhang, S. Bottega, O. Guicherit, H. Wichterle, H. Dudek, D. Bumcrot, F. Wang, S. Jones, J. Shulok, L. Rubin, and J. Porter J. Biol. 1 2002 10
- (2002) J. Biol. , vol.1 , pp. 10
- Frank-Kamenetsky, M.¹ Zhang, X.² Bottega, S.³ Guicherit, O.⁴ Wichterle, H.⁵ Dudek, H.⁶ Bumcrot, D.⁷ Wang, F.⁸ Jones, S.⁹ Shulok, J.¹⁰ Rubin, L.¹¹ Porter, J.¹²

34
- 0037447269
- J. Williams, O. Guicherit, B. Zaharian, Y. Xu, L. Chai, H. Wichterle, C. Kon, C. Gatchalian, J. Porter, L. Rubin, and F. Wang Proc. Natl. Acad. Sci. U.S.A. 100 2003 4616 4621
- (2003) Proc. Natl. Acad. Sci. U.S.A. , vol.100 , pp. 4616-4621
- Williams, J.¹ Guicherit, O.² Zaharian, B.³ Xu, Y.⁴ Chai, L.⁵ Wichterle, H.⁶ Kon, C.⁷ Gatchalian, C.⁸ Porter, J.⁹ Rubin, L.¹⁰ Wang, F.¹¹

35
- 70449371472
- C. Sheridan Nat. Biotechnol. 27 2009 968 969
- (2009) Nat. Biotechnol. , vol.27 , pp. 968-969
- Sheridan, C.¹

36
- 70349244812
- C. Rudin, C. Hann, J. Laterra, R. Yauch, C. Callahan, L. Fu, T. Holcomb, J. Stinson, S. Gould, B. Coleman, P. LoRusso, D. von Hoff, F. de Sauvage, and J. Low N. Engl. J. Med. 361 2009 1173 1178
- (2009) N. Engl. J. Med. , vol.361 , pp. 1173-1178
- Rudin, C.¹ Hann, C.² Laterra, J.³ Yauch, R.⁴ Callahan, C.⁵ Fu, L.⁶ Holcomb, T.⁷ Stinson, J.⁸ Gould, S.⁹ Coleman, B.¹⁰ Lorusso, P.¹¹ Von Hoff, D.¹² De Sauvage, F.¹³ Low, J.¹⁴

37
- 70350496540
- R. Yauch, G. Dijkgraaf, B. Alicke, T. Januario, C. Ahn, T. Holcomb, K. Pujara, J. Stinson, C. Callahan, T. Tang, T. Bazan, Z. Kan, S. Seshagiri, C. Hann, S. Gould, J. Low, C. Rudin, and F. de Sauvage Science 326 2009 572 574
- (2009) Science , vol.326 , pp. 572-574
- 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, T.¹¹ Kan, Z.¹² Seshagiri, S.¹³ Hann, C.¹⁴ Gould, S.¹⁵ Low, J.¹⁶ Rudin, C.¹⁷ De Sauvage, F.¹⁸

38
- 0018232837
- R.F. Keeler Lipids 13 1978 708 715
- (1978) Lipids , vol.13 , pp. 708-715
- Keeler, R.F.¹

39
- 67649476250
- For a preliminary account of the synthesis and biological evaluation of 6, see
- For a preliminary account of the synthesis and biological evaluation of 6, see J. Winkler, A. Isaacs, L. Holderbaum, V. Tatard, and N. Dahmane Org. Lett. 11 2009 2824 2827
- (2009) Org. Lett. , vol.11 , pp. 2824-2827
- Winkler, J.¹ Isaacs, A.² Holderbaum, L.³ Tatard, V.⁴ Dahmane, N.⁵

40
- 0034738979
- For a preliminary account of the synthesis and biological evaluation of 7 and 8, see: Isaacs, A.; Xiang, C.; Baubet, V.; Dahmane, N.; Winkler, J. Org. Lett., in press.: J. Taipale, J.K. Chen, M.K. Cooper, B. Wang, R.K. Mann, L. Milenkovic, M.P. Scott, and P.A. Beachy Nature 406 2000 1005 1009
- (2000) Nature , vol.406 , pp. 1005-1009
- Taipale, J.¹ Chen, J.K.² Cooper, M.K.³ Wang, B.⁴ Mann, R.K.⁵ Milenkovic, L.⁶ Scott, M.P.⁷ Beachy, P.A.⁸

41
- 85023453181
- J. Williams, and G. Sarkisia Synthesis 1974 32 33
- (1974) Synthesis , pp. 32-33
- Williams, J.¹ Sarkisia, G.²

42
- 5244370033
- A.B. Pangborn, M.A. Giardello, R.H. Grubbs, R.K. Rosen, and F.J. Trimmers Organometallics 15 1996 1518
- (1996) Organometallics , vol.15 , pp. 1518
- Pangborn, A.B.¹ Giardello, M.A.² Grubbs, R.H.³ Rosen, R.K.⁴ Trimmers, F.J.⁵

43
- 77951452357
- C. Fernandez, V. Tatard, N. Bertrand, and N. Dahmane Dev. Neurosci. 32 2010 59 70
- (2010) Dev. Neurosci. , vol.32 , pp. 59-70
- Fernandez, C.¹ Tatard, V.² Bertrand, N.³ Dahmane, N.⁴

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