SCOPUS 정보 검색 플랫폼

European Journal of Organic Chemistry

Volumn , Issue 32, 2011, Pages 6507-6518

Synthesis of new dopamine D1 antagonist SCH 23390 analogues by the stereoselective stevens rearrangement

(4) Ariza, Manuela a Díaz, Amelia a Suau, Rafael a Valpuesta, María a

a UNIVERSITY OF MÁLAGA (Spain)

Author keywords

Medicinal chemistry; Nitrogen heterocycles; Rearrangement; Stereoselectivity; Ylides

Indexed keywords

EID: 80155211059 PISSN: 1434193X EISSN: 10990690 Source Type: Journal
DOI: 10.1002/ejoc.201100991 Document Type: Article

Times cited : (14)

References (50)

1
- 0028951501
- K. K. Gnanalingham, A. J. Hunter, P. Jenner, C. D. Marsden, Psychopharmacology 1995, 117, 403-412.
- (1995) Psychopharmacology , vol.117 , pp. 403-412
- Gnanalingham, K.K.¹ Hunter, A.J.² Jenner, P.³ Marsden, C.D.⁴

2
- 34248562939
- A. D. Medhurst, A. R. Atkins, I. J. Beresford, K. Brachenborough, M. A. Briggs, A. R. Calver, J. Cilia, J. E. Cluderay, B. Crook, J. B. Davis, R. K. Davis, R. P. Davis, L. A. Dawson, A. G. Foley, J. Gartlon, M. I. Gonzalez, T. Heslop, W. D. Hirst, C. Jennings, D. N. C. Jones, L. P. Lacroix, A. Martyn, S. Ociepka, A. Ray, C. M. Regan, J. C. Roberts, J. Schogger, E. Southam, T. O. Stean, B. K. Trail, N. Upton, G. Wadsworth, J. A. Wald, T. White, J. Witherington, M. L. Woolley, A. Worby, D. M. Wilson, J. Pharmacol. Exp. Ther. 2007, 321, 1032-1045.
- (2007) J. Pharmacol. Exp. Ther. , vol.321 , pp. 1032-1045
- Medhurst, A.D.¹ Atkins, A.R.² Beresford, I.J.³ Brachenborough, K.⁴ Briggs, M.A.⁵ Calver, A.R.⁶ Cilia, J.⁷ Cluderay, J.E.⁸ Crook, B.⁹ Davis, J.B.¹⁰ Davis, R.K.¹¹ Davis, R.P.¹² Dawson, L.A.¹³ Foley, A.G.¹⁴ Gartlon, J.¹⁵ Gonzalez, M.I.¹⁶ Heslop, T.¹⁷ Hirst, W.D.¹⁸ Jennings, C.¹⁹ Jones, D.N.C.²⁰ more..

3
- 0035727179
- J. A. Bourne, CNS Drug Rev. 2001, 7, 399-414.
- (2001) CNS Drug Rev. , vol.7 , pp. 399-414
- Bourne, J.A.¹

4
- 33846905526
- A. Zhang, J. L. Neumeyer, R. J. Baldessarini, Chem. Rev. 2007, 107, 274-302.
- (2007) Chem. Rev. , vol.107 , pp. 274-302
- Zhang, A.¹ Neumeyer, J.L.² Baldessarini, R.J.³

5
- 62249211062
- J. Zhang, B. Xiong, X. Zhen, A. Zhang, Med. Res. Rev. 2009, 29, 272-294.
- (2009) Med. Res. Rev. , vol.29 , pp. 272-294
- Zhang, J.¹ Xiong, B.² Zhen, X.³ Zhang, A.⁴

6
- 80155201248
- U.S. Patent 4284555
- E. H. Gold, W. K. Chang, U.S. Patent 4284555, 1981.
- (1981)
- Gold, E.H.¹ Chang, W.K.²

7
- 0020506608
- L. C. Iorio, A. Barnett, F. H. Leitz, V. P. Houser, C. A. Korduba, Pharmacology 1983, 226, 462-468.
- (1983) Pharmacology , vol.226 , pp. 462-468
- Iorio, L.C.¹ Barnett, A.² Leitz, F.H.³ Houser, V.P.⁴ Korduba, C.A.⁵

8
- 0024336333
- J. G. Berger, W. K. Chang, J. W. Clader, D. Hou, R. E. Chipkin, A. T. McPhail, J. Med. Chem. 1989, 32, 1913-1921.
- (1989) J. Med. Chem. , vol.32 , pp. 1913-1921
- Berger, J.G.¹ Chang, W.K.² Clader, J.W.³ Hou, D.⁴ Chipkin, R.E.⁵ McPhail, A.T.⁶

9
- 0026615559
- 119S-122S.
- A. Barnett, R. D. McQuade, C. Tedford, Neurochem. Int. 1992, 20, 119S-122S.
- (1992) Neurochem. Int. , vol.20
- Barnett, A.¹ McQuade, R.D.² Tedford, C.³

10
- 0030788305
- A. F. Schtzberg, P. Haddad, E. M. Kaplan, M. Lejoyeux, J. F. Rosenbaum, A. H. Young, J. Zajecka, J. Clin. Psychiatry 1997, 58, 5-10.
- (1997) J. Clin. Psychiatry , vol.58 , pp. 5-10
- Schtzberg, A.F.¹ Haddad, P.² Kaplan, E.M.³ Lejoyeux, M.⁴ Rosenbaum, J.F.⁵ Young, A.H.⁶ Zajecka, J.⁷

11
- 0035004706
- M. Haney, A. S. Ward, R. W. Foltin, M. W. Fischman, Psychopharmacology 2001, 155, 330-337.
- (2001) Psychopharmacology , vol.155 , pp. 330-337
- Haney, M.¹ Ward, A.S.² Foltin, R.W.³ Fischman, M.W.⁴

12
- 0034743920
- E. Nann-Vernptica, E. C. Donny, G. E. Bigelow, S. L. Walsh, Psychopharmacology 2001, 155, 338-347.
- (2001) Psychopharmacology , vol.155 , pp. 338-347
- Nann-Vernptica, E.¹ Donny, E.C.² Bigelow, G.E.³ Walsh, S.L.⁴

13
- 80155151197
- WO Patent 19990301
- V. L. Coffin, WO Patent 19990301, 1999.
- (1999)
- Coffin, V.L.¹

14
- 80155179304
- WO Patent 9921540
- V. Coffin, P. W. Glue, WO Patent 9921540, 1999.
- (1999)
- Coffin, V.¹ Glue, P.W.²

15
- 34547954712
- A. Astrup, F. L. Greenway, W. Ling, L. Pedicone, J. Lachowicz, C. D. Strader, R. Kwan, Obesity 2007, 15, 1717-1731.
- (2007) Obesity , vol.15 , pp. 1717-1731
- Astrup, A.¹ Greenway, F.L.² Ling, W.³ Pedicone, L.⁴ Lachowicz, J.⁵ Strader, C.D.⁶ Kwan, R.⁷

16
- 0026094347
- R. D. McQuade, R. A. Duffy, V. L. Coffin, R. E. Chipkin, A. Barnett, J. Pharmacol. Exp. Ther. 1991, 257, 42-49.
- (1991) J. Pharmacol. Exp. Ther. , vol.257 , pp. 42-49
- McQuade, R.D.¹ Duffy, R.A.² Coffin, V.L.³ Chipkin, R.E.⁴ Barnett, A.⁵

17
- 0026648067
- P. H. Andersen, F. C. Gronvald, R. Hohlweg, L. B. Hansen, E. Guddal, C. Braestrup, E. B. Nielsen, Eur. J. Pharmacol. 1992, 219, 45-52.
- (1992) Eur. J. Pharmacol. , vol.219 , pp. 45-52
- Andersen, P.H.¹ Gronvald, F.C.² Hohlweg, R.³ Hansen, L.B.⁴ Guddal, E.⁵ Braestrup, C.⁶ Nielsen, E.B.⁷

18
- 74049162090
- L. Qiang, T. K. Sasikumar, D. A. Burnett, J. Su, H. Tang, Y. Ye, R. D. Mazzola, Z. Zhu, B. A. McKittrick, W. J. Greenlee, A. Fawzi, M. Smith, H. Zhang, J. E. Lachowicz, Bioorg. Med. Chem. Lett. 2010, 20, 836-840.
- (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 836-840
- Qiang, L.¹ Sasikumar, T.K.² Burnett, D.A.³ Su, J.⁴ Tang, H.⁵ Ye, Y.⁶ Mazzola, R.D.⁷ Zhu, Z.⁸ McKittrick, B.A.⁹ Greenlee, W.J.¹⁰ Fawzi, A.¹¹ Smith, M.¹² Zhang, H.¹³ Lachowicz, J.E.¹⁴

19
- 74049099560
- T. K. Sasikumar, D. A. Burnett, W. J. Greenlee, M. Smith, A. Fawzi, H. Zhang, J. E. Lachowicz, Bioorg. Med. Chem. Lett. 2010, 20, 832-835.
- (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 832-835
- Sasikumar, T.K.¹ Burnett, D.A.² Greenlee, W.J.³ Smith, M.⁴ Fawzi, A.⁵ Zhang, H.⁶ Lachowicz, J.E.⁷

20
- 34948834767
- R. Feneck, Drugs 2007, 67, 2023-2044.
- (2007) Drugs , vol.67 , pp. 2023-2044
- Feneck, R.¹

21
- 80155151194
- W. K. Chang, M. Peters, V. P. Fevig, J. A. Kozlowski, G. Zhou, D. B. Lowe, H. Guzik, R. D. McQuade, R. Duffy, V. L. Coffin, J. G. Berger, Bioorg. Med. Chem. Lett. 1992, 2, 339-402.
- (1992) Bioorg. Med. Chem. Lett. , vol.2 , pp. 339-402
- Chang, W.K.¹ Peters, M.² Fevig, V.P.³ Kozlowski, J.A.⁴ Zhou, G.⁵ Lowe, D.B.⁶ Guzik, H.⁷ McQuade, R.D.⁸ Duffy, R.⁹ Coffin, V.L.¹⁰ Berger, J.G.¹¹

22
- 68349131456
- Z. Zhu, Z.-Y. Sun, Y. Ye, B. Mckittrick, W. Greenlee, M. Czarniecki, A. Fawzi, H. Zhang, J. E. Lachowicz, Bioorg. Med. Chem. Lett. 2009, 19, 5218-5221.
- (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 5218-5221
- Zhu, Z.¹ Sun, Z.-Y.² Ye, Y.³ McKittrick, B.⁴ Greenlee, W.⁵ Czarniecki, M.⁶ Fawzi, A.⁷ Zhang, H.⁸ Lachowicz, J.E.⁹

23
- 77955396906
- M. Valpuesta, M. Ariza, A. Díaz, R. Suau, Eur. J. Org. Chem. 2010, 4393-4401.
- (2010) Eur. J. Org. Chem. , pp. 4393-4401
- Valpuesta, M.¹ Ariza, M.² Díaz, A.³ Suau, R.⁴

24
- 74949099493
- M. Valpuesta, M. Ariza, A. Díaz, R. Suau, Eur. J. Org. Chem. 2010, 638-645.
- (2010) Eur. J. Org. Chem. , pp. 638-645
- Valpuesta, M.¹ Ariza, M.² Díaz, A.³ Suau, R.⁴

25
- 0035965118
- A. R. Katritzky, H.-Y. He, R. Jiang, Q. Long, Tetrahedron: Asymmetry 2001, 12, 2427-2434.
- (2001) Tetrahedron: Asymmetry , vol.12 , pp. 2427-2434
- Katritzky, A.R.¹ He, H.-Y.² Jiang, R.³ Long, Q.⁴

26
- 0000314374
- C. Locher, N. Peerzada, J. Chem. Soc. Perkin Trans. 1 1999, 179-184.
- (1999) J. Chem. Soc. Perkin Trans. 1 , pp. 179-184
- Locher, C.¹ Peerzada, N.²

27
- 29144452454
- W. Cui, K. Iwasa, H. Tokuda, A. Kashihara, Y. Mitani, T. Hasegawa, Y. Nishiyama, M. Moriyasu, H. Nishino, M. Hanaoka, C. Mukai, K. Takeda, Phytochemistry 2006, 67, 70-79.
- (2006) Phytochemistry , vol.67 , pp. 70-79
- Cui, W.¹ Iwasa, K.² Tokuda, H.³ Kashihara, A.⁴ Mitani, Y.⁵ Hasegawa, T.⁶ Nishiyama, Y.⁷ Moriyasu, M.⁸ Nishino, H.⁹ Hanaoka, M.¹⁰ Mukai, C.¹¹ Takeda, K.¹²

28
- 5744254384
- A. B. J. Bracca.
- A. B. J. Bracca, T. S. Kaufman, Tetrahedron 2004, 60, 10575-10610.
- (2004) Tetrahedron , vol.60 , pp. 10575-10610
- Kaufman, T.S.¹

29
- 0034742834
- M. R. Pitts, J. R. Harrison, C. J. Moody, J. Chem. Soc. Perkin Trans. 1 2001, 955-977.
- (2001) J. Chem. Soc. Perkin Trans. 1 , pp. 955-977
- Pitts, M.R.¹ Harrison, J.R.² Moody, C.J.³

30
- 0344327052
- M. Valpuesta, A. Díaz, R. Suau, Phytochemistry 1999, 51, 1157-1160.
- (1999) Phytochemistry , vol.51 , pp. 1157-1160
- Valpuesta, M.¹ Díaz, A.² Suau, R.³

31
- 33646892194
- S. Smith Jr.
- S. Smith Jr., V. Elango, M. Shamma, J. Org. Chem. 1984, 49, 581-586.
- (1984) J. Org. Chem. , vol.49 , pp. 581-586
- Elango, V.¹ Shamma, M.²

32
- 0039575003
- Y. Sato, N. Shirai, Y. Machida, E. Ito, T. Yasui, Y. Kurono, K. Hatano, J. Org. Chem. 1992, 57, 6711-6716.
- (1992) J. Org. Chem. , vol.57 , pp. 6711-6716
- Sato, Y.¹ Shirai, N.² MacHida, Y.³ Ito, E.⁴ Yasui, T.⁵ Kurono, Y.⁶ Hatano, K.⁷

33
- 0037899660
- Tinker software package, rev. 4, see: P. Ren, J. W. Ponder, J. Phys. Chem. B 2003, 107, 5933-5947.
- (2003) J. Phys. Chem. B , vol.107 , pp. 5933-5947
- Ren, P.¹ Ponder, J.W.²

34
- 0036890275
- P. Ren, J. W. Ponder, J. Comput. Chem. 2002, 23, 1497-1506.
- (2002) J. Comput. Chem. , vol.23 , pp. 1497-1506
- Ren, P.¹ Ponder, J.W.²

35
- 0038424321
- R. V. Pappu, R. K. Hart, J. W. Ponder, J. Phys. Chem. B 1998, 102, 9725-9742.
- (1998) J. Phys. Chem. B , vol.102 , pp. 9725-9742
- Pappu, R.V.¹ Hart, R.K.² Ponder, J.W.³

36
- 0030573021
- M. E. Hodsdon, J. W. Ponder, D. P. Cistola, J. Mol. Biol. 1996, 264, 585-602.
- (1996) J. Mol. Biol. , vol.264 , pp. 585-602
- Hodsdon, M.E.¹ Ponder, J.W.² Cistola, D.P.³

37
- 84986533794
- C. E. Kundrot, J. W. Ponder, F. M. Richards, J. Comput. Chem. 1991, 12, 402-409.
- (1991) J. Comput. Chem. , vol.12 , pp. 402-409
- Kundrot, C.E.¹ Ponder, J.W.² Richards, F.M.³

38
- 84988112508
- J. W. Ponder, F. M. Richards, J. Comput. Chem. 1987, 8, 1016-1024.
- (1987) J. Comput. Chem. , vol.8 , pp. 1016-1024
- Ponder, J.W.¹ Richards, F.M.²

39
- 54049092884
- M. Movassaghi, M. D. Hill, Org. Lett. 2008, 10, 3485-3488.
- (2008) Org. Lett. , vol.10 , pp. 3485-3488
- Movassaghi, M.¹ Hill, M.D.²

40
- 58149151072
- J. Jacobs, N. van Tuyen, P. Markusse, C. V. Stevens, L. Maat, N. De Kimpe, Tetrahedron 2009, 65, 1188-1192.
- (2009) Tetrahedron , vol.65 , pp. 1188-1192
- Jacobs, J.¹ Van Tuyen, N.² Markusse, P.³ Stevens, C.V.⁴ Maat, L.⁵ De Kimpe, N.⁶

41
- 33747720806
- J. Tõth, A. Dancsõ, G. Blaskõ, L. Tõke, P. W. Groundwater, M. Nyerges, Tetrahedron 2006, 62, 5725-5735.
- (2006) Tetrahedron , vol.62 , pp. 5725-5735
- Tõth, J.¹ Dancsõ, A.² Blaskõ, G.³ Tõke, L.⁴ Groundwater, P.W.⁵ Nyerges, M.⁶

42
- 73349120908
- L. Evanno, J. Ormala, P. M. Pihko, Chem. Eur. J. 2009, 15, 12963-12967.
- (2009) Chem. Eur. J. , vol.15 , pp. 12963-12967
- Evanno, L.¹ Ormala, J.² Pihko, P.M.³

43
- 0037078252
- M. T. Herrero, I. Tellitu, E. Domínguez, S. Hernández, I. Moreno, R. SanMartín, Tetrahedron 2002, 58, 8581-8589.
- (2002) Tetrahedron , vol.58 , pp. 8581-8589
- Herrero, M.T.¹ Tellitu, I.² Domínguez, E.³ Hernández, S.⁴ Moreno, I.⁵ Sanmartín, R.⁶

44
- 63049115952
- F. I. Zubkov, J. D. Ershova, A. A. Orlova, V. P. Zaytsev, E. V. Nikitina, A. S. Peregudov, A. V. Gurbanov, R. S. Borisov, V. N. Khrustalev, A. M. Maharramov, A. V. Varlamov, Tetrahedron 2009, 65, 3789-3803.
- (2009) Tetrahedron , vol.65 , pp. 3789-3803
- Zubkov, F.I.¹ Ershova, J.D.² Orlova, A.A.³ Zaytsev, V.P.⁴ Nikitina, E.V.⁵ Peregudov, A.S.⁶ Gurbanov, A.V.⁷ Borisov, R.S.⁸ Khrustalev, V.N.⁹ Maharramov, A.M.¹⁰ Varlamov, A.V.¹¹

45
- 84981864256
- W. Wenner, M. Stefaniw, J. Heterocycl. Chem. 1967, 4, 469-473.
- (1967) J. Heterocycl. Chem. , vol.4 , pp. 469-473
- Wenner, W.¹ Stefaniw, M.²

46
- 80155165288
- C. Jerassi, J. J. Beerebooms, P. Marfey, S. K. Figdor, J. Am. Chem. Soc. 1955, 77, 485-486.
- (1955) J. Am. Chem. Soc. , vol.77 , pp. 485-486
- Jerassi, C.¹ Beerebooms, J.J.² Marfey, P.³ Figdor, S.K.⁴

47
- 37049110829
- J. M. Barker, P. R. Huddleston, J. Clephane, M. L. Wood, D. Holmes, J. Chem. Soc. Perkin Trans. 1 1985, 275-281.
- (1985) J. Chem. Soc. Perkin Trans. 1 , pp. 275-281
- Barker, J.M.¹ Huddleston, P.R.² Clephane, J.³ Wood, M.L.⁴ Holmes, D.⁵

48
- 0000973521
- T. Shono, H. Hamaguchi, M. Sasaki, S. Fujita, K. Nagami, J. Org. Chem. 1983, 48, 1621-1628.
- (1983) J. Org. Chem. , vol.48 , pp. 1621-1628
- Shono, T.¹ Hamaguchi, H.² Sasaki, M.³ Fujita, S.⁴ Nagami, K.⁵

49
- 41149092492
- P. Cheng, N. Huang, Z.-Y. Jiang, Q. Zhang, Y.-T. Zheng, J.-J. Chen, X.-M. Zhang, Y.-B. Ma, Bioorg. Med. Chem. Lett. 2008, 18, 2475-2478.
- (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 2475-2478
- Cheng, P.¹ Huang, N.² Jiang, Z.-Y.³ Zhang, Q.⁴ Zheng, Y.-T.⁵ Chen, J.-J.⁶ Zhang, X.-M.⁷ Ma, Y.-B.⁸

50
- 45249116186
- G. S. Gimranova, S. A. Soldatova, A. T. Soldatenkov, K. B. Polyanskii, Russ. J. Org. Chem. 2008, 44, 750-754.
- (2008) Russ. J. Org. Chem. , vol.44 , pp. 750-754
- Gimranova, G.S.¹ Soldatova, S.A.² Soldatenkov, A.T.³ Polyanskii, K.B.⁴

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.