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Volumn 9, Issue 23, 2011, Pages 8016-8029

Exploitation of an additional hydrophobic pocket of σ 1 receptors: Late-stage diverse modifications of spirocyclic thiophenes by C-H bond functionalization

(8) Meyer, Christina a Neue, Benedikt a Schepmann, Dirk a Yanagisawa, Shuichi b Yamaguchi, Junichiro b Würthwein, Ernst Ulrich a Itami, Kenichiro b Wünsch, Bernhard a

a UNIVERSITY OF MÜNSTER (Germany)

b NAGOYA UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL GROUP; BIPYRIDYL; C-H BOND; CATALYST SYSTEM; DFT CALCULATION; FUNCTIONALIZATIONS; HYDROPHOBIC BINDING; HYDROPHOBIC POCKETS; PHARMACOPHORE MODELS; PHENYL MOIETIES; PYRAZOLE DERIVATIVES; RECEPTOR LIGANDS; RECEPTOR PROTEINS; SUBSTITUTION PATTERNS; THIOPHENE DERIVATIVES;

CHELATION; DENSITY FUNCTIONAL THEORY; HYDROPHOBICITY; NAPHTHALENE; THIOPHENE;

LIGANDS;

CARBON; HYDROGEN; LIGAND; SPIRO COMPOUND; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY;

CARBON; HYDROGEN; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SPIRO COMPOUNDS; THIOPHENES;

EID: 81255128914 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c1ob06149f Document Type: Article

Times cited : (33)

References (52)

1
- 0025651756
- J. M. Walker W. D. Bowen F. O. Walker R. R. Matsumoto B. De Costa K. C. Rice Pharmacol. Rev. 1990 42 355 402
- (1990) Pharmacol. Rev. , vol.42 , pp. 355-402
- Walker, J.M.¹ Bowen, W.D.² Walker, F.O.³ Matsumoto, R.R.⁴ De Costa, B.⁵ Rice, K.C.⁶

2
- 45949118722
- R. Quirion R. Chicheportiche P. C. Contreras K. M. Johnson D. Lodge S. W. Tam J. H. Woods S. R. Zukin Trends Neurosci. 1987 10 444 446
- (1987) Trends Neurosci. , vol.10 , pp. 444-446
- Quirion, R.¹ Chicheportiche, R.² Contreras, P.C.³ Johnson, K.M.⁴ Lodge, D.⁵ Tam, S.W.⁶ Woods, J.H.⁷ Zukin, S.R.⁸

3
- 0026567933
- R. Quirion W. D. Bowen Y. Itzhak J. L. Junien J. M. Musachio R. B. Rothman T. P. Su S. W. Tam D. P. Taylor Trends Pharmacol. Sci. 1992 13 85 86
- (1992) Trends Pharmacol. Sci. , vol.13 , pp. 85-86
- Quirion, R.¹ Bowen, W.D.² Itzhak, Y.³ Junien, J.L.⁴ Musachio, J.M.⁵ Rothman, R.B.⁶ Su, T.P.⁷ Tam, S.W.⁸ Taylor, D.P.⁹

4
- 1942485807
- T. Hayashi T. P. Su CNS Drugs 2004 18 269 284
- (2004) CNS Drugs , vol.18 , pp. 269-284
- Hayashi, T.¹ Su, T.P.²

5
- 66149149075
- E. J. Cobos J. M. Entrena F. R. Nieto C. M. Cendan E. DelPezo Curr. Pharmacol. 2008 6 344 366
- (2008) Curr. Pharmacol. , vol.6 , pp. 344-366
- Cobos, E.J.¹ Entrena, J.M.² Nieto, F.R.³ Cendan, C.M.⁴ Delpezo, E.⁵

6
- 70349116879
- T. Maurice T. P. Su Pharmacol. Ther. 2009 124 195 206
- (2009) Pharmacol. Ther. , vol.124 , pp. 195-206
- Maurice, T.¹ Su, T.P.²

7
- 74049130162
- M. Ishikawa K. Hashimoto J. Receptor Ligand Channel Res. 2010 3 25 36
- (2010) J. Receptor Ligand Channel Res. , vol.3 , pp. 25-36
- Ishikawa, M.¹ Hashimoto, K.²

8
- 0028795145
- B. J. Vilner C. S. John W. D. Bowen Cancer Res. 1995 55 408 413
- (1995) Cancer Res. , vol.55 , pp. 408-413
- Vilner, B.J.¹ John, C.S.² Bowen, W.D.³

9
- 8644261553
- B. Wang R. Rouzier C. T. Albarracin A. Sahin P. Wagner Y. Yang T. L. Smith F. M. Bernstam A. C. Marcelo G. N. Hortobagyi L. Pusztai Breast Cancer Res. Treat. 2004 87 205 214
- (2004) Breast Cancer Res. Treat. , vol.87 , pp. 205-214
- Wang, B.¹ Rouzier, R.² Albarracin, C.T.³ Sahin, A.⁴ Wagner, P.⁵ Yang, Y.⁶ Smith, T.L.⁷ Bernstam, F.M.⁸ Marcelo, A.C.⁹ Hortobagyi, G.N.¹⁰ Pusztai, L.¹¹

10
- 0034469983
- K. Kitaichi J. G. Chabot F. F. Moebius A. Flandorfer H. Glossmann R. Quirion J. Chem. Neuroanat. 2000 20 375 387
- (2000) J. Chem. Neuroanat. , vol.20 , pp. 375-387
- Kitaichi, K.¹ Chabot, J.G.² Moebius, F.F.³ Flandorfer, A.⁴ Glossmann, H.⁵ Quirion, R.⁶

11
- 0033841625
- P. J. Lupardus R A. Wilke E. Aydar C. P. Palmer Y. Chen A. E. Ruoho M. B. Jackson J. Physiol. 2000 526 527 539
- (2000) J. Physiol. , vol.526 , pp. 527-539
- Lupardus, P.J.¹ Wilke, R.A.² Aydar, E.³ Palmer, C.P.⁴ Chen, Y.⁵ Ruoho, A.E.⁶ Jackson, M.B.⁷

12
- 0037171847
- E. Aydar C. P. Palmer V. A. Klyachko M B. Jackson Neuron 2002 34 399 410
- (2002) Neuron , vol.34 , pp. 399-410
- Aydar, E.¹ Palmer, C.P.² Klyachko, V.A.³ Jackson, M.B.⁴

13
- 0028233908
- C. Ela J. Barg Z. Vogel Y. Hasin Y. Eilam J. Pharmacol. Exp. Ther. 1994 269 1300 1309
- (1994) J. Pharmacol. Exp. Ther. , vol.269 , pp. 1300-1309
- Ela, C.¹ Barg, J.² Vogel, Z.³ Hasin, Y.⁴ Eilam, Y.⁵

14
- 66149100423
- M. Johannessen S. Ramachandran L. Riemer A. Ramos-Serrano A. E. Ruoho M. B. Jackson Am. J. Physiol.: Cell Physiol. 2009 296 C1049 C1057
- (2009) Am. J. Physiol.: Cell Physiol. , vol.296
- Johannessen, M.¹ Ramachandran, S.² Riemer, L.³ Ramos-Serrano, A.⁴ Ruoho, A.E.⁵ Jackson, M.B.⁶

15
- 84856073454
- submitted
- T. Schläger D. Schepmann K. Lehmkuhl J. Holenz J. M. Vela H. Buschmann B. Wünsch J. Med. Chem.
- J. Med. Chem.
- Schläger, T.¹ Schepmann, D.² Lehmkuhl, K.³ Holenz, J.⁴ Vela, J.M.⁵ Buschmann, H.⁶ Wünsch, B.⁷

16
- 54549085666
- C. Oberdorf D. Schepmann J. M. Vela, J. L. Diaz J. Holenz B. Wünsch J. Med. Chem. 2008 51 6531 6537
- (2008) J. Med. Chem. , vol.51 , pp. 6531-6537
- Oberdorf, C.¹ Schepmann, D.² Vela, J.M.³ Diaz, J.L.⁴ Holenz, J.⁵ Wünsch, B.⁶

17
- 77954346690
- C. Oberdorf T. J. Schmidt B. Wünsch Eur. J. Med. Chem. 2010 45 3116 3124
- (2010) Eur. J. Med. Chem. , vol.45 , pp. 3116-3124
- Oberdorf, C.¹ Schmidt, T.J.² Wünsch, B.³

18
- 79956193000
- E. Rack R. Fröhlich D. Schepmann B. Wünsch Bioorg. Med. Chem. 2011 19 3141 3151
- (2011) Bioorg. Med. Chem. , vol.19 , pp. 3141-3151
- Rack, E.¹ Fröhlich, R.² Schepmann, D.³ Wünsch, B.⁴

19
- 0028268389
- R. A. Glennon S. Y. Ablordeppey A. M. Ismaiel M. B. El-Ashmawy J. B. Fischer K. B. Howie J. Med. Chem. 1994 37 1214 1219
- (1994) J. Med. Chem. , vol.37 , pp. 1214-1219
- Glennon, R.A.¹ Ablordeppey, S.Y.² Ismaiel, A.M.³ El-Ashmawy, M.B.⁴ Fischer, J.B.⁵ Howie, K.B.⁶

20
- 24944497780
- R. A. Glennon Mini-Rev. Med. Chem. 2005 5 927 940
- (2005) Mini-Rev. Med. Chem. , vol.5 , pp. 927-940
- Glennon, R.A.¹

21
- 23844457000
- C. Laggner C. Schieferer B. Fiechtner G. Poles R. D. Hoffmann H. Glossmann T. Langer E. F. Moebius J. Med. Chem. 2005 48 4754 4764
- (2005) J. Med. Chem. , vol.48 , pp. 4754-4764
- Laggner, C.¹ Schieferer, C.² Fiechtner, B.³ Poles, G.⁴ Hoffmann, R.D.⁵ Glossmann, H.⁶ Langer, T.⁷ Moebius, E.F.⁸

22
- 69949100924
- D. Zampieri M. G. Mamolo E. Laurini C. Florio C. Zanette M. Fermeglia P. Posocco M. S. Paneni S. Pricl L. Vio J. Med. Chem. 2009 52 5380 5393
- (2009) J. Med. Chem. , vol.52 , pp. 5380-5393
- Zampieri, D.¹ Mamolo, M.G.² Laurini, E.³ Florio, C.⁴ Zanette, C.⁵ Fermeglia, M.⁶ Posocco, P.⁷ Paneni, M.S.⁸ Pricl, S.⁹ Vio, L.¹⁰

23
- 81255170651
- Serena Software, Version 9.1, Bloomington, Indiana, USA
- PCMODEL, Serena Software, Version 9.1, 2005, Bloomington, Indiana, USA
- (2005) PCMODEL

24
- 0000189651
- D. Becke J. Chem. Phys. 1993 98 5648
- (1993) J. Chem. Phys. , vol.98 , pp. 5648
- Becke, D.¹

25
- 0345491105
- C. Lee W. Yang R. G. Parr Phys. Rev. B 1988 37 785 789
- (1988) Phys. Rev. B , vol.37 , pp. 785-789
- Lee, C.¹ Yang, W.² Parr, R.G.³

26
- 0038617502
- S. J. Grimme J. Chem. Phys. 2003 118 9095 9102
- (2003) J. Chem. Phys. , vol.118 , pp. 9095-9102
- Grimme, S.J.¹

28
- 37049087628
- D. W. Hawkins B. Iddon D. S. Longthorne P. J. Rosyk J. Chem. Soc., Perkin Trans. 1 1994 2735 2743
- (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 2735-2743
- Hawkins, D.W.¹ Iddon, B.² Longthorne, D.S.³ Rosyk, P.J.⁴

29
- 0025115953
- B. Wünsch Arch. Pharm. 1990 323 493 499
- (1990) Arch. Pharm. , vol.323 , pp. 493-499
- Wünsch, B.¹

30
- 0036589259
- J. Hassan M. Sévignon C. Gozzi E. Schulz M. Lemaire Chem. Rev. 2002 102 1359
- (2002) Chem. Rev. , vol.102 , pp. 1359
- Hassan, J.¹ Sévignon, M.² Gozzi, C.³ Schulz, E.⁴ Lemaire, M.⁵

31
- 33846918696
- D. Alberico M. E. Scott M. Lautens Chem. Rev. 2007 107 174
- (2007) Chem. Rev. , vol.107 , pp. 174
- Alberico, D.¹ Scott, M.E.² Lautens, M.³

32
- 72449170089
- L. Ackermann R. Vicente A. R. Kapdti Angew. Chem., Int. Ed. 2009 48 9792
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 9792
- Ackermann, L.¹ Vicente, R.² Kapdti, A.R.³

33
- 0000882066
- A. Ohta Y. Akita T. Ohkuwa M. Chiba R. Fukunaga A. Miyafuji T. Nakata N. Tani Y. Aoyagi Heterocycles 1990 31 1951
- (1990) Heterocycles , vol.31 , pp. 1951
- Ohta, A.¹ Akita, Y.² Ohkuwa, T.³ Chiba, M.⁴ Fukunaga, R.⁵ Miyafuji, A.⁶ Nakata, T.⁷ Tani, N.⁸ Aoyagi, Y.⁹

34
- 64249118769
- references therein
- B. Liégault D. Lapointe L. Caron A. Vlassova K. Fagnou J. Org. Chem. 2009 74 1826
- (2009) J. Org. Chem. , vol.74 , pp. 1826
- Liégault, B.¹ Lapointe, D.² Caron, L.³ Vlassova, A.⁴ Fagnou, K.⁵

35
- 33748515918
- S. Yanagisawa T. Sudo R. Noyori K. Itami J. Am. Chem. Soc. 2006 128 11748
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 11748
- Yanagisawa, S.¹ Sudo, T.² Noyori, R.³ Itami, K.⁴

36
- 43849100263
- S. Yanagisawa T. Sudo R. Noyori K. Itami Tetrahedron 2008 64 6073
- (2008) Tetrahedron , vol.64 , pp. 6073
- Yanagisawa, S.¹ Sudo, T.² Noyori, R.³ Itami, K.⁴

37
- 70349915658
- J. Benoît T. Yamamoto K. Itami Angew. Chem., Int. Ed. 2009 48 3644
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 3644
- Benoît, J.¹ Yamamoto, T.² Itami, K.³

38
- 57349113866
- H.-Q. Do R. M. K. Khan O. Daugulis J. Am. Chem. Soc. 2008 130 15185
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 15185
- Do, H.-Q.¹ Khan, R.M.K.² Daugulis, O.³

39
- 70350054836
- S. Yanagisawa K. Ueda H. Sekizawa K. Itami J. Am. Chem. Soc. 2009 131 14622
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 14622
- Yanagisawa, S.¹ Ueda, K.² Sekizawa, H.³ Itami, K.⁴

40
- 78449231481
- K. Ueda S. Yanagisawa J. Yamaguchi K. Itami Angew. Chem., Int. Ed. 2010 49 8946
- (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 8946
- Ueda, K.¹ Yanagisawa, S.² Yamaguchi, J.³ Itami, K.⁴

41
- 79952050537
- S. Kirchberg S. Tani K. Ueda J. Yamaguchi A. Studer K. Itami Angew. Chem. Int. Ed. 2011 50 2387
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 2387
- Kirchberg, S.¹ Tani, S.² Ueda, K.³ Yamaguchi, J.⁴ Studer, A.⁵ Itami, K.⁶

42
- 79957517035
- S. Yanagisawa K. Itami Tetrahedron 2011 67 4425
- (2011) Tetrahedron , vol.67 , pp. 4425
- Yanagisawa, S.¹ Itami, K.²

43
- 0037122746
- C. A. Maier B. Wünsch J. Med. Chem. 2002 45 438 448
- (2002) J. Med. Chem. , vol.45 , pp. 438-448
- Maier, C.A.¹ Wünsch, B.²

44
- 0037168069
- C. A. Maier B. Wünsch J. Med. Chem. 2002 45 4923 4930
- (2002) J. Med. Chem. , vol.45 , pp. 4923-4930
- Maier, C.A.¹ Wünsch, B.²

45
- 65349159284
- E. Große Maestrup C. Wiese D. Schepmann A. Hiller S. Fischer M. Scheunemann P. Brust B. Wünsch Bioorg. Med. Chem. 2009 17 3630 3641
- (2009) Bioorg. Med. Chem. , vol.17 , pp. 3630-3641
- Große Maestrup, E.¹ Wiese, C.² Schepmann, D.³ Hiller, A.⁴ Fischer, S.⁵ Scheunemann, M.⁶ Brust, P.⁷ Wünsch, B.⁸

46
- 64549128253
- R. Holl D. Schepmann R. Fröhlich R. Grünert P. J. Bednarski B. Wünsch J. Med. Chem. 2009 52 2126 2137
- (2009) J. Med. Chem. , vol.52 , pp. 2126-2137
- Holl, R.¹ Schepmann, D.² Fröhlich, R.³ Grünert, R.⁴ Bednarski, P.J.⁵ Wünsch, B.⁶

47
- 0031913686
- P. D. Prasad H. W. Li Y. J. Fei M. E. Ganapathy T. Fujita L. H. Plumley T. L. Yang-Feng F. H. Leibach V. Ganapathy J. Neurochem. 1998 70 443 451
- (1998) J. Neurochem. , vol.70 , pp. 443-451
- Prasad, P.D.¹ Li, H.W.² Fei, Y.J.³ Ganapathy, M.E.⁴ Fujita, T.⁵ Plumley, L.H.⁶ Yang-Feng, T.L.⁷ Leibach, F.H.⁸ Ganapathy, V.⁹

48
- 33845184366
- J. Suffert J. Org. Chem. 1989 54 509 510
- (1989) J. Org. Chem. , vol.54 , pp. 509-510
- Suffert, J.¹

49
- 0017184389
- M. M. Bradford Anal. Biochem. 1976 72 248 254
- (1976) Anal. Biochem. , vol.72 , pp. 248-254
- Bradford, M.M.¹

50
- 0027078540
- D. L. DeHaven-Hudkins L. C. Fleissner F. Y. Ford-Rice Eur. J. Pharmacol., Mol. Pharmacol. Sect. 1992 227 371 378
- (1992) Eur. J. Pharmacol., Mol. Pharmacol. Sect. , vol.227 , pp. 371-378
- Dehaven-Hudkins, D.L.¹ Fleissner, L.C.² Ford-Rice, F.Y.³

51
- 0028891399
- H. Mach C. R. Smith S. R. Childers Life Sci. 1995 57 PL57
- (1995) Life Sci. , vol.57 , pp. 57
- MacH, H.¹ Smith, C.R.² Childers, S.R.³

52
- 0015861774
- Y. C. Cheng W. H. Prusoff Biochem. Pharmacol. 1973 22 3099 3108
- (1973) Biochem. Pharmacol. , vol.22 , pp. 3099-3108
- Cheng, Y.C.¹ Prusoff, W.H.²

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