SCOPUS 정보 검색 플랫폼

Volumn 12, Issue 29, 2014, Pages 5407-5426

Synthesis and pharmacological evaluation of like- and unlike-configured tetrahydro-2-benzazepines with the α-substituted benzyl moiety in the 5-position

(6) Hasebein, Peer a Frehland, Bastian a Lehmkuhl, Kirstin a Fröhlich, Roland a Schepmann, Dirk a Wünsch, Bernhard a

a UNIVERSITY OF MÜNSTER (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ETHERS; KETONES;

BENZYL MOIETIES; DIASTEREOMERIC; HIGH AFFINITY LIGANDS; MITSUNOBU INVERSION; P-METHOXYBENZYL; REDUCTIVE CYCLIZATION; STETTER REACTION; SYNTHETIC STRATEGIES;

LIGANDS;

BENZAZEPINE DERIVATIVE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; SIGMA OPIATE RECEPTOR;

ANIMAL; BINDING SITE; CHEMISTRY; CONFORMATION; GUINEA PIG; METABOLISM; RAT; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANIMALS; BENZAZEPINES; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; GUINEA PIGS; MOLECULAR CONFORMATION; RATS; RECEPTORS, N-METHYL-D-ASPARTATE; RECEPTORS, SIGMA;

EID: 84903765731 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c4ob00510d Document Type: Article

Times cited : (72)

References (55)

1
- 0017064976
- W. R. Martin C. G. Eades J. A. Thompson R. E. Huppler P. E. Gilbert J. Pharmacol. Exp. Ther. 1976 197 517 532
- (1976) J. Pharmacol. Exp. Ther. , vol.197 , pp. 517-532
- Martin, W.R.¹ Eades, C.G.² Thompson, J.A.³ Huppler, R.E.⁴ Gilbert, P.E.⁵

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
- 35549006797
- T. Hayashi T.-P. Su Cell 2007 131 596 610
- (2007) Cell , vol.131 , pp. 596-610
- Hayashi, T.¹ Su, T.-P.²

5
- 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

6
- 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

7
- 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

8
- 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

9
- 0037047305
- D. A. Meyer M. Carta L. D. Partridge D. F. Covey C. F. Valenzuela J. Biol. Chem. 2002 277 28725 28732
- (2002) J. Biol. Chem. , vol.277 , pp. 28725-28732
- Meyer, D.A.¹ Carta, M.² Partridge, L.D.³ Covey, D.F.⁴ Valenzuela, C.F.⁵

10
- 57649133946
- Z. Wu W. D. Bowen J. Biol. Chem. 2008 283 28198 28215
- (2008) J. Biol. Chem. , vol.283 , pp. 28198-28215
- Wu, Z.¹ Bowen, W.D.²

11
- 0035895206
- T. Hayashi T.-P. Su Proc. Natl. Acad. Sci. U. S. A. 2001 98 491 496
- (2001) Proc. Natl. Acad. Sci. U. S. A. , vol.98 , pp. 491-496
- Hayashi, T.¹ Su, T.-P.²

12
- 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

13
- 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

14
- 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

15
- 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

16
- 34250218876
- J. A. Butera J. Med. Chem. 2007 50 2543 2546
- (2007) J. Med. Chem. , vol.50 , pp. 2543-2546
- Butera, J.A.¹

17
- 34250170786
- J. D. Kennedy J. Med. Chem. 2007 50 2547 2556
- (2007) J. Med. Chem. , vol.50 , pp. 2547-2556
- Kennedy, J.D.¹

18
- 67349154763
- J. M. Entrena E. J. Cobos F. R. Nieto C. M. Cendan G. Gris E. Del Pozo D. Zampanillo J. M. Baeyens Pain 2009 143 252 261
- (2009) Pain , vol.143 , pp. 252-261
- Entrena, J.M.¹ Cobos, E.J.² Nieto, F.R.³ Cendan, C.M.⁴ Gris, G.⁵ Del Pozo, E.⁶ Zampanillo, D.⁷ Baeyens, J.M.⁸

19
- 69249149994
- J. L. Diaz D. Zamanillo J. Corbera J. M. Baeyens R. Maldonado M. A. Pericas J. M. Vela A. Torrens Cent. Nerv. Syst. Agents Med. Chem. 2009 9 172 183
- (2009) Cent. Nerv. Syst. Agents Med. Chem. , vol.9 , pp. 172-183
- Diaz, J.L.¹ Zamanillo, D.² Corbera, J.³ Baeyens, J.M.⁴ Maldonado, R.⁵ Pericas, M.A.⁶ Vela, J.M.⁷ Torrens, A.⁸

20
- 33746280830
- J. Corbera D. Vaño D. Martínez J. M. Vela D. Zamanillo A. Dordal F. Andreu E. Hernandez R. Perez M. Escriche L. Salgado S. Yeste M. T. Serafini R. Pascual J. Alegre M. C. Calvet N. Cano M. Carro H. Buschmann J. Holenz Chem. Med. Chem. 2006 1 140 154
- (2006) Chem. Med. Chem. , vol.1 , pp. 140-154
- Corbera, J.¹ Vaño, D.² Martínez, D.³ Vela, J.M.⁴ Zamanillo, D.⁵ Dordal, A.⁶ Andreu, F.⁷ Hernandez, E.⁸ Perez, R.⁹ Escriche, M.¹⁰ Salgado, L.¹¹ Yeste, S.¹² Serafini, M.T.¹³ Pascual, R.¹⁴ Alegre, J.¹⁵ Calvet, M.C.¹⁶ Cano, N.¹⁷ Carro, M.¹⁸ Buschmann, H.¹⁹ Holenz, J.²⁰ more..

21
- 84867387612
- J. L. Diaz R. Cuberes J. Berrocal M. Contijoch U. Christmann A. Fernández A. Port J. Holenz H. Buschmann C. Laggner M. T. Serafini J. Burgeno D. Zamanillo M. Merlos J. M. Vela C. Almansa J. Med. Chem. 2012 55 8211 8224
- (2012) J. Med. Chem. , vol.55 , pp. 8211-8224
- Diaz, J.L.¹ Cuberes, R.² Berrocal, J.³ Contijoch, M.⁴ Christmann, U.⁵ Fernández, A.⁶ Port, A.⁷ Holenz, J.⁸ Buschmann, H.⁹ Laggner, C.¹⁰ Serafini, M.T.¹¹ Burgeno, J.¹² Zamanillo, D.¹³ Merlos, M.¹⁴ Vela, J.M.¹⁵ Almansa, C.¹⁶

22
- 84867340616
- B. Wünsch J. Med. Chem. 2012 55 8209 8210
- (2012) J. Med. Chem. , vol.55 , pp. 8209-8210
- Wünsch, B.¹

23
- 84876671257
- E. Laurini V. Dal Col S. Pricl B. Wünsch Bioorg. Med. Chem. Lett. 2013 23 2868 2871
- (2013) Bioorg. Med. Chem. Lett. , vol.23 , pp. 2868-2871
- Laurini, E.¹ Dal Col, V.² Pricl, S.³ Wünsch, B.⁴

24
- 80955128570
- E. Laurini V. Dal Col M. G. Mamolo D. Zampieri P. Posocco M. Fermeglia V. Vio S. Pricl ACS Med. Chem. Lett. 2011 2 834 839
- (2011) ACS Med. Chem. Lett. , vol.2 , pp. 834-839
- Laurini, E.¹ Dal Col, V.² Mamolo, M.G.³ Zampieri, D.⁴ Posocco, P.⁵ Fermeglia, M.⁶ Vio, V.⁷ Pricl, S.⁸

25
- 84900532376
- S. Brune D. Schepmann K.-H. Klempnauer D. Marson V. Dal Col E. Laurini M. Fermeglia B. Wünsch S. Pricl Biochem. 2014 53 18 2993 3003
- (2014) Biochem. , vol.53 , Issue.18 , pp. 2993-3003
- Brune, S.¹ Schepmann, D.² Klempnauer, K.-H.³ Marson, D.⁴ Dal Col, V.⁵ Laurini, E.⁶ Fermeglia, M.⁷ Wünsch, B.⁸ Pricl, S.⁹

26
- 84876961205
- P. Hasebein K. Aulinger D. Schepmann B. Wünsch Tetrahedron 2013 69 4552 4562
- (2013) Tetrahedron , vol.69 , pp. 4552-4562
- Hasebein, P.¹ Aulinger, K.² Schepmann, D.³ Wünsch, B.⁴

27
- 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

28
- 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

29
- 23844457000
- C. Laggner C. Schieferer B. Fiechtner G. Poles R. D. Hoffmann H. Glossmann T. Langer F. F. Moebius J. Med. Chem. 2005 48 4754
- (2005) J. Med. Chem. , vol.48 , pp. 4754
- Laggner, C.¹ Schieferer, C.² Fiechtner, B.³ Poles, G.⁴ Hoffmann, R.D.⁵ Glossmann, H.⁶ Langer, T.⁷ Moebius, F.F.⁸

30
- 84905264461
- 10.1002/cmdc.201402110
- P. Hasebein B. Frehland D. Schepmann B. Wünsch Chem. Med. Chem. 2014 10.1002/cmdc.201402110
- (2014) Chem. Med. Chem.
- Hasebein, P.¹ Frehland, B.² Schepmann, D.³ Wünsch, B.⁴

31
- 84856846240
- A. Tarcsay K. Nyiri G. M. Keseerü J. Med. Chem. 2012 55 1252 1260
- (2012) J. Med. Chem. , vol.55 , pp. 1252-1260
- Tarcsay, A.¹ Nyiri, K.² Keseerü, G.M.³

32
- 84982347903
- H. Stetter M. Schrekenberg Chem. Ber. 1974 107 210 214
- (1974) Chem. Ber. , vol.107 , pp. 210-214
- Stetter, H.¹ Schrekenberg, M.²

33
- 2742589161
- H. Stetter M. Schrekenberg Angew. Chem. Int. Ed. Engl. 1973 85 89
- (1973) Angew. Chem. Int. Ed. Engl. , vol.85 , pp. 89
- Stetter, H.¹ Schrekenberg, M.²

34
- 84876828644
- J. Wencel-Delord F. Glorius Nat. Chem. 2013 5 369 375
- (2013) Nat. Chem. , vol.5 , pp. 369-375
- Wencel-Delord, J.¹ Glorius, F.²

35
- 81255128914
- C. Meyer B. Neue D. Schepmann S. Yanagisawa J. Yamaguchi E.-U. Würthwein K. Itami B. Wünsch Org. Biomol. Chem. 2011 9 8016 8029
- (2011) Org. Biomol. Chem. , vol.9 , pp. 8016-8029
- Meyer, C.¹ Neue, B.² Schepmann, D.³ Yanagisawa, S.⁴ Yamaguchi, J.⁵ Würthwein, E.-U.⁶ Itami, K.⁷ Wünsch, B.⁸

36
- 0003586140
- B. Classon J. Garregg B. Samuelsson Acta Chem. Scand. 1984 419 422
- (1984) Acta Chem. Scand. , pp. 419-422
- Classon, B.¹ Garregg, J.² Samuelsson, B.³

37
- 37049109459
- R. Jonhansson B. Samuelsson J. Chem. Soc., Perkin Trans. 1 1984 2371 2374
- (1984) J. Chem. Soc., Perkin Trans. 1 , pp. 2371-2374
- Jonhansson, R.¹ Samuelsson, B.²

38
- 67649386488
- K. C. Kumara Swamy N. N. Bhuvan Kumar E. Balaraman K. V. P. Pavan Kumar Chem. Rev. 2009 109 2551 2651
- (2009) Chem. Rev. , vol.109 , pp. 2551-2651
- Kumara Swamy, K.C.¹ Bhuvan Kumar, N.N.² Balaraman, E.³ Pavan Kumar, K.V.P.⁴

39
- 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

40
- 84875212566
- C. Meyer B. Neue D. Schepmann S. Yanagisawa J. Yamaguchi E.-U. Würthwein K. Itami B. Wünsch Bioorg. Med. Chem. 2013 21 1844 1856
- (2013) Bioorg. Med. Chem. , vol.21 , pp. 1844-1856
- Meyer, C.¹ Neue, B.² Schepmann, D.³ Yanagisawa, S.⁴ Yamaguchi, J.⁵ Würthwein, E.-U.⁶ Itami, K.⁷ Wünsch, B.⁸

41
- 0026635198
- F. I. Caroll P. Abraham K. Parham X. Bai X. Zhang G. A. Brine S. W. Mascarella B. R. Martin F. L. May C. Sauss L. Di Paolo P. Wallace J. M. Walker W. D. Bowen J. Med. Chem. 1992 35 2812 2818
- (1992) J. Med. Chem. , vol.35 , pp. 2812-2818
- Caroll, F.I.¹ Abraham, P.² Parham, K.³ Bai, X.⁴ Zhang, X.⁵ Brine, G.A.⁶ Mascarella, S.W.⁷ Martin, B.R.⁸ May, F.L.⁹ Sauss, C.¹⁰ Di Paolo, L.¹¹ Wallace, P.¹² Walker, J.M.¹³ Bowen, W.D.¹⁴

42
- 0028028245
- E. L. May M. D. Aceto E. R. Bowman C. Bentley B. R. Martin C. S. Harris F. Medzihradsky M. V. Mattson A. E. Jacobson J. Med. Chem. 1994 37 3408 3418
- (1994) J. Med. Chem. , vol.37 , pp. 3408-3418
- May, E.L.¹ Aceto, M.D.² Bowman, E.R.³ Bentley, C.⁴ Martin, B.R.⁵ Harris, C.S.⁶ Medzihradsky, F.⁷ Mattson, M.V.⁸ Jacobson, A.E.⁹

43
- 84903774871
- T. Utech J. Köhler B. Wünsch Eur. J. Med. Chem. 2011 46 2257 2169
- (2011) Eur. J. Med. Chem. , vol.46 , pp. 2257-2169
- Utech, T.¹ Köhler, J.² Wünsch, B.³

44
- 84867835631
- J. Köhler K. Bergander J. Fabian D. Schepmann B. Wünsch J. Med. Chem. 2012 55 8953 8957
- (2012) J. Med. Chem. , vol.55 , pp. 8953-8957
- Köhler, J.¹ Bergander, K.² Fabian, J.³ Schepmann, D.⁴ Wünsch, B.⁵

45
- 1542301638
- O. Krull B. Wünsch Bioorg. Med. Chem. 2004 12 1439 1451
- (2004) Bioorg. Med. Chem. , vol.12 , pp. 1439-1451
- Krull, O.¹ Wünsch, B.²

46
- 78449248928
- A. Banerjee D. Schepmann J. Köhler E.-U. Würthwein B. Wünsch Bioorg. Med. Chem. 2010 18 7855 7867
- (2010) Bioorg. Med. Chem. , vol.18 , pp. 7855-7867
- Banerjee, A.¹ Schepmann, D.² Köhler, J.³ Würthwein, E.-U.⁴ Wünsch, B.⁵

47
- 0031059866
- Z. Otwinowski W. Minor Methods Enzymol. 1997 276 307 326
- (1997) Methods Enzymol. , vol.276 , pp. 307-326
- Otwinowski, Z.¹ Minor, W.²

48
- 0038414570
- Z. Otwinowski D. Borek W. Majewski W. Minor Acta Crystallogr., Sect. A: Fundam. Crystallogr. 2003 59 228 234
- (2003) Acta Crystallogr., Sect. A: Fundam. Crystallogr. , vol.59 , pp. 228-234
- Otwinowski, Z.¹ Borek, D.² Majewski, W.³ Minor, W.⁴

49
- 84943920736
- G. M. Sheldrick Acta Crystallogr., Sect. A: Fundam. Crystallogr. 1990 46 467 473
- (1990) Acta Crystallogr., Sect. A: Fundam. Crystallogr. , vol.46 , pp. 467-473
- Sheldrick, G.M.¹

50
- 37549039510
- G. M. Sheldrick Acta Crystallogr., Sect. A: Fundam. Crystallogr. 2008 64 112 122
- (2008) Acta Crystallogr., Sect. A: Fundam. Crystallogr. , vol.64 , pp. 112-122
- Sheldrick, G.M.¹

51
- 0017184389
- M. M. A. Bradford Anal. Biochem. 1976 72 248 254
- (1976) Anal. Biochem. , vol.72 , pp. 248-254
- Bradford, M.M.A.¹

52
- 0025211779
- C. Stoscheck Methods Enzymol. 1990 182 50 68
- (1990) Methods Enzymol. , vol.182 , pp. 50-68
- Stoscheck, C.¹

53
- 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

54
- 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

55
- 0028891399
- H. Mach C. R. Smith S. R. Childers Life Sci. 1995 57 PL-57-62
- (1995) Life Sci. , vol.57 , pp. 57-62
- Mach, H.¹ Smith, C.R.² Childers, S.R.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.