SCOPUS 정보 검색 플랫폼

Volumn 6, Issue 18, 2008, Pages 3388-3398

Diastereoselective functionalizations of enecarbamates derived from pipecolic acid towards 5-guanidinopipecolates as arginine mimetics

(6) Le Corre, Laurent a Kizirian, Jean Claude a,b Levraud, Camille a Boucher, Jean Luc a Bonnet, Véronique a,c Dhimane, Hamid a

a UNIVERSITÉ PARIS DESCARTES (France)

b UNIVERSITÉ DE TOURS (France)

c UNIVERSITÉ DE PICARDIE JULES VERNE (France)

Author keywords

[No Author keywords available]

Indexed keywords

NITRIC OXIDE;

CARBON DOUBLE BONDS; DIASTEREOSELECTIVE; DIASTEREOSELECTIVE SYNTHESIS; FREE RADICALS; FUNCTIONALIZATIONS; ISOFORMS; MIMETICS; NITRIC-OXIDE SYNTHASE; PIPECOLIC ACID; POTENTIAL INHIBITION;

AMINO ACIDS;

AMINE; ARGININE; AZIDE; BIOMIMETIC MATERIAL; CARBAMIC ACID DERIVATIVE; DRUG DERIVATIVE; ENZYME INHIBITOR; GUANIDINE; KETONE; NITRIC OXIDE SYNTHASE; PIPECOLIC ACID; PIPECOLIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; HYDROXYLATION; METABOLISM; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

AMINES; ARGININE; AZIDES; BIOMIMETIC MATERIALS; CARBAMATES; ENZYME INHIBITORS; GUANIDINE; HYDROXYLATION; KETONES; MOLECULAR STRUCTURE; NITRIC OXIDE SYNTHASE; OXIDATION-REDUCTION; PIPECOLIC ACIDS; STEREOISOMERISM;

EID: 52749086063 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/b805811c Document Type: Article

Times cited : (34)

References (58)

1
- 0019991071
- -588
- Y. F. Chang Neurochem. Res. 1982 7 577 588
- (1982) Neurochem. Res. , vol.7 , pp. 577
- Chang, Y.F.¹

2
- 0034696831
- -1105
- L. IJlst I. de Kromme W. Oostheim R. J. Wanders Biochem. Biophys. Res. Commun. 2000 270 1101 1105
- (2000) Biochem. Biophys. Res. Commun. , vol.270 , pp. 1101
- Ijlst, L.¹ De Kromme, I.² Oostheim, W.³ Wanders, R.J.⁴

3
- 0030793060
- -6447
- T. M. Zabriskie W. L. Kelly X. Liang J. Am. Chem. Soc. 1997 119 6446 6447
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 6446
- Zabriskie, T.M.¹ Kelly, W.L.² Liang, X.³

4
- 0032969622
- -320
- F. Couty Amino Acids 1999 16 297 320
- (1999) Amino Acids , vol.16 , pp. 297
- Couty, F.¹

5
- 23944496414
- -130
- C. Kadouri-Puchot S. Comesse Amino Acids 2005 29 101 130
- (2005) Amino Acids , vol.29 , pp. 101
- Kadouri-Puchot, C.¹ Comesse, S.²

6
- 34249290099
- -6541
- W. Gu M. Cueto P. R. Jensen W. Fenical R. B. Silverman Tetrahedron 2007 63 6535 6541
- (2007) Tetrahedron , vol.63 , pp. 6535
- Gu, W.¹ Cueto, M.² Jensen, P.R.³ Fenical, W.⁴ Silverman, R.B.⁵

7
- 0029864732
- -3536
- Z. Zhao X. Liu Z. Shi L. Danley B. Huang R.-T. Jiang M.-D. Tsai J. Am. Chem. Soc. 1996 118 3535 3536
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 3535
- Zhao, Z.¹ Liu, X.² Shi, Z.³ Danley, L.⁴ Huang, B.⁵ Jiang, R.-T.⁶ Tsai, M.-D.⁷

8
- 0025296462
- -314
- T. D. Copeland E. M. Wondrak J. Tozser M. M. Roberts S. Oroszlan Biochem. Biophys. Res. Commun. 1990 169 310 314
- (1990) Biochem. Biophys. Res. Commun. , vol.169 , pp. 310
- Copeland, T.D.¹ Wondrak, E.M.² Tozser, J.³ Roberts, M.M.⁴ Oroszlan, S.⁵

9
- 0030594982
- -1936
- G. J. Hanson J. L. Vuletich L. J. Bedell C. P. Bono S. C. Howard J. K. Welply S. L. Woulfe M. L. Zacheis Bioorg. Med. Chem. Lett. 1996 6 1931 1936
- (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 1931
- Hanson, G.J.¹ Vuletich, J.L.² Bedell, L.J.³ Bono, C.P.⁴ Howard, S.C.⁵ Welply, J.K.⁶ Woulfe, S.L.⁷ Zacheis, M.L.⁸

10
- 0028350462
- -1166
- G. T. Wang B. Lane S. W. Fesik A. Petros J. Luly G. A. Krafft Bioorg. Med. Chem. Lett. 1994 4 1161 1166
- (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 1161
- Wang, G.T.¹ Lane, B.² Fesik, S.W.³ Petros, A.⁴ Luly, J.⁵ Krafft, G.A.⁶

11
- 0028559927
- -14451
- Y. Tsuda M. Cygler B. F. Gibbs A. Pedyczak J. Féthière S. Y. Yue Y. Konishi Biochemistry 1994 33 14443 14451
- (1994) Biochemistry , vol.33 , pp. 14443
- Tsuda, Y.¹ Cygler, M.² Gibbs, B.F.³ Pedyczak, A.⁴ Féthière, J.⁵ Yue, S.Y.⁶ Konishi, Y.⁷

12
- 0028783283
- -4453
- R. T. Shuman R. B. Rothenberger C. S. Campbell G. F. Smith D. S. Gifford-Moore J. W. Paschal P. D. Gesellchen J. Med. Chem. 1995 38 4446 4453
- (1995) J. Med. Chem. , vol.38 , pp. 4446
- Shuman, R.T.¹ Rothenberger, R.B.² Campbell, C.S.³ Smith, G.F.⁴ Gifford-Moore, D.S.⁵ Paschal, J.W.⁶ Gesellchen, P.D.⁷

13
- 0034697723
- -1871
- W. Maison A. Lützen M. Kosten I. Schlemminger O. Westerhoff W. Saak J. Martens J. Chem. Soc., Perkin Trans. 1 2000 1867 1871
- (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 1867
- Maison, W.¹ Lützen, A.² Kosten, M.³ Schlemminger, I.⁴ Westerhoff, O.⁵ Saak, W.⁶ Martens, J.⁷

14
- 0027397579
- -866
- M. J. Genin W. B. Gleason R. L. Johnson J. Org. Chem. 1993 58 860 866
- (1993) J. Org. Chem. , vol.58 , pp. 860
- Genin, M.J.¹ Gleason, W.B.² Johnson, R.L.³

15
- 0029887905
- -1878
- P. J. Murray I. D. Starkey Tetrahedron Lett. 1996 37 1875 1878
- (1996) Tetrahedron Lett. , vol.37 , pp. 1875
- Murray, P.J.¹ Starkey, I.D.²

16
- 0037164662
- -10428
- D.-G. Liu X.-Z. Wang Y. Gao B. Li D. Yang T. R. Burke Tetrahedron 2002 58 10423 10428
- (2002) Tetrahedron , vol.58 , pp. 10423
- Liu, D.-G.¹ Wang, X.-Z.² Gao, Y.³ Li, B.⁴ Yang, D.⁵ Burke, T.R.⁶

17
- 0032539509
- -394
- P. L. Ornstein M. B. Arnold W. H. Lunn L. J. Heinz J. D. Leander D. Lodge D. D. Schoepp Bioorg. Med. Chem. Lett. 1998 8 389 394
- (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 389
- Ornstein, P.L.¹ Arnold, M.B.² Lunn, W.H.³ Heinz, L.J.⁴ Leander, J.D.⁵ Lodge, D.⁶ Schoepp, D.D.⁷

18
- 0032897645
- -408
- S. Brocherieux-Lanoy H. Dhimane C. Vanucci-Bacqué G. Lhommet Synlett 1999 405 408
- (1999) Synlett , pp. 405
- Brocherieux-Lanoy, S.¹ Dhimane, H.² Vanucci-Bacqué, C.³ Lhommet, G.⁴

19
- 0037170138
- -1648
- H. Dhimane S. Meunier C. Vanucci-Bacqué G. Lhommet Tetrahedron Lett. 2002 43 1645 1648
- (2002) Tetrahedron Lett. , vol.43 , pp. 1645
- Dhimane, H.¹ Meunier, S.² Vanucci-Bacqué, C.³ Lhommet, G.⁴

20
- 0035338986
- -949
- M. David H. Dhimane C. Vanucci-Bacqué G. Lhommet Heterocycles 2001 55 941 949
- (2001) Heterocycles , vol.55 , pp. 941
- David, M.¹ Dhimane, H.² Vanucci-Bacqué, C.³ Lhommet, G.⁴

21
- 26444504184
- -7497
- L. Le Corre H. Dhimane Tetrahedron Lett. 2005 46 7495 7497
- (2005) Tetrahedron Lett. , vol.46 , pp. 7495
- Le Corre, L.¹ Dhimane, H.²

22
- 0001349480
- -245
- S. Torii T. Inokuchi F. Akahoshi M. Kubota Synthesis 1987 242 245
- (1987) Synthesis , pp. 242
- Torii, S.¹ Inokuchi, T.² Akahoshi, F.³ Kubota, M.⁴

23
- 0001208332
- -4074
- T. Shono Y. Matsumura O. Onomura Y. Yamada Tetrahedron Lett. 1987 28 4073 4074
- (1987) Tetrahedron Lett. , vol.28 , pp. 4073
- Shono, T.¹ Matsumura, Y.² Onomura, O.³ Yamada, Y.⁴

24
- 0028111674
- -6882
- T. Martens F. Souquet J. Royer Tetrahedron Lett. 1994 35 6879 6882
- (1994) Tetrahedron Lett. , vol.35 , pp. 6879
- Martens, T.¹ Souquet, F.² Royer, J.³

25
- 12344337506
- -1244
- M. Norton Matos C. A. Afonso R. A. Batey Tetrahedron 2005 61 1221 1244
- (2005) Tetrahedron , vol.61 , pp. 1221
- Norton, M.M.¹ Afonso, C.A.² Batey, R.A.³

26
- 12344325648
- -4944
- P. N. Botman F. J. Dommerholt R. de Gelder Q. B. Broxterman H. E. Schoemaker F. P. Rutjes R. Blaauw Org. Lett. 2004 6 4941 4944
- (2004) Org. Lett. , vol.6 , pp. 4941
- Botman, P.N.¹ Dommerholt, F.J.² De Gelder, R.³ Broxterman, Q.B.⁴ Schoemaker, H.E.⁵ Rutjes, F.P.⁶ Blaauw, R.⁷

27
- 33846190694
- -E35
- S. S. Libendi T. Ogino O. Onomura Y. Matsumura J. Electrochem. Soc. 2007 154 E31 E35
- (2007) J. Electrochem. Soc. , vol.154 , pp. 31
- Libendi, S.S.¹ Ogino, T.² Onomura, O.³ Matsumura, Y.⁴

28
- 0023715081
- -4121
- T. Shono Y. Matsumura O. Onomura M. Sato J. Org. Chem. 1988 53 4118 4121
- (1988) J. Org. Chem. , vol.53 , pp. 4118
- Shono, T.¹ Matsumura, Y.² Onomura, O.³ Sato, M.⁴

29
- 0030580351
- -8398
- Y. Matsumura T. Kinoshita Y. Yanagihara N. Kanemoto M. Watanabe Tetrahedron Lett. 1996 37 8395 8398
- (1996) Tetrahedron Lett. , vol.37 , pp. 8395
- Matsumura, Y.¹ Kinoshita, T.² Yanagihara, Y.³ Kanemoto, N.⁴ Watanabe, M.⁵

30
- 0001589412
- -208
- M. David H. Dhimane C. Vanucci-Bacqué G. Lhommet Synlett 1998 206 208
- (1998) Synlett , pp. 206
- David, M.¹ Dhimane, H.² Vanucci-Bacqué, C.³ Lhommet, G.⁴

31
- 0026001558
- -6726
- T. Shono Y. Matsumura T. Fujita Tetrahedron Lett. 1991 32 6723 6726
- (1991) Tetrahedron Lett. , vol.32 , pp. 6723
- Shono, T.¹ Matsumura, Y.² Fujita, T.³

32
- 0002543115
- -1963
- H. Dhimane C. Vanucci-Bacqué L. Hamon G. Lhommet Eur. J. Org. Chem. 1998 1955 1963
- (1998) Eur. J. Org. Chem. , pp. 1955
- Dhimane, H.¹ Vanucci-Bacqué, C.² Hamon, L.³ Lhommet, G.⁴

33
- 0000353228
- -6764
- H. C. Brown K. W. Kim T. E. Cole B. Singaram J. Am. Chem. Soc. 1986 108 6761 6764
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 6761
- Brown, H.C.¹ Kim, K.W.² Cole, T.E.³ Singaram, B.⁴

34
- 0029131063
- -7486
- K. Fujimoto Y. Tokuda Y. Matsubara H. Maekawa T. Mizuno I. Nishiguchi Tetrahedron Lett. 1995 36 7483 7486
- (1995) Tetrahedron Lett. , vol.36 , pp. 7483
- Fujimoto, K.¹ Tokuda, Y.² Matsubara, Y.³ Maekawa, H.⁴ Mizuno, T.⁵ Nishiguchi, I.⁶

35
- 0033516684
- -5074
- S. P. Chavan Y. T. Subbarao Tetrahedron Lett. 1999 40 5073 5074
- (1999) Tetrahedron Lett. , vol.40 , pp. 5073
- Chavan, S.P.¹ Subbarao, Y.T.²

36
- 0035479540
- -7010
- M. R. Norton Matos C. A. Afonso R. A. Batey Tetrahedron Lett. 2001 42 7007 7010
- (2001) Tetrahedron Lett. , vol.42 , pp. 7007
- Norton, R.M.M.¹ Afonso, C.A.² Batey, R.A.³

37
- 0027484384
- -7570
- M. Plehiers C. Hootelé Tetrahedron Lett. 1993 34 7569 7570
- (1993) Tetrahedron Lett. , vol.34 , pp. 7569
- Plehiers, M.¹ Hootelé, C.²

38
- 0001291188
- -2793
- A. Suzuki N. Miyaura M. Itoh J. Am. Chem. Soc. 1971 93 2792 2793
- (1971) J. Am. Chem. Soc. , vol.93 , pp. 2792
- Suzuki, A.¹ Miyaura, N.² Itoh, M.³

39
- 0027250674
- -2094
- C. Herdeis E. Heller Tetrahedron: Asymmetry 1993 4 2085 2094
- (1993) Tetrahedron: Asymmetry , vol.4 , pp. 2085
- Herdeis, C.¹ Heller, E.²

40
- 0033516314
- -5076
- R. Batey D. MacKay V. Santhakumar J. Am. Chem. Soc. 1999 121 5075 5076
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 5075
- Batey, R.¹ MacKay, D.² Santhakumar, V.³

41
- 0035830556
- Addition of citric acid (1.5 equiv.) gave faster reactions in the case of substrates 3a,b; however, no such effect was observed with 3c. Similar kinetic enhancement, with various olefins, was first reported by Sharpless and co-workers: -823
- O. Okitsu R. Suzuki S. Kobayashi J. Org. Chem. 2001 66 809 823
- (2001) J. Org. Chem. , vol.66 , pp. 809
- Okitsu, O.¹ Suzuki, R.² Kobayashi, S.³

42
- 0000451948
- -433
- P. Dupau R. Epple A. A. Thomas V. V. Fokin K. B. Sharpless Adv. Synth. Catal. 2002 344 421 433
- (2002) Adv. Synth. Catal. , vol.344 , pp. 421
- Dupau, P.¹ Epple, R.² Thomas, A.A.³ Fokin, V.V.⁴ Sharpless, K.B.⁵

43
- 0037467849
- -909
- S. Rani Y. D. Vankar Tetrahedron Lett. 2003 44 907 909
- (2003) Tetrahedron Lett. , vol.44 , pp. 907
- Rani, S.¹ Vankar, Y.D.²

44
- 0032554991
- -3416
- C. H. Sugisaki P. J. Carroll C. R. Correia Tetrahedron Lett. 1998 39 3413 3416
- (1998) Tetrahedron Lett. , vol.39 , pp. 3413
- Sugisaki, C.H.¹ Carroll, P.J.² Correia, C.R.³

45
- 0032569868
- -8888
- M. Sunose K. M. Anderson A. G. Orpen T. Gallagher S. J. Macdonald Tetrahedron Lett. 1998 39 8885 8888
- (1998) Tetrahedron Lett. , vol.39 , pp. 8885
- Sunose, M.¹ Anderson, K.M.² Orpen, A.G.³ Gallagher, T.⁴ MacDonald, S.J.⁵

46
- 0000517303
- -2825
- Y. L. Chow C. J. Colon J. N. Tam Can. J. Chem. 1968 46 2821 2825
- (1968) Can. J. Chem. , vol.46 , pp. 2821
- Chow, Y.L.¹ Colon, C.J.² Tam, J.N.³

47
- 49549155726
- -4172
- R. R. Fraser T. B. Grindley Tetrahedron Lett. 1974 15 4169 4172
- (1974) Tetrahedron Lett. , vol.15 , pp. 4169
- Fraser, R.R.¹ Grindley, T.B.²

48
- 0000424631
- -371
- C. Ludwig L.-G. Wistrand Acta Chem. Scand. 1994 48 367 371
- (1994) Acta Chem. Scand. , vol.48 , pp. 367
- Ludwig, C.¹ Wistrand, L.-G.²

49
- 33751499964
- -2800
- A. G. Barrett D. Pilipauska J. Org. Chem. 1991 56 2787 2800
- (1991) J. Org. Chem. , vol.56 , pp. 2787
- Barrett, A.G.¹ Pilipauska, D.²

50
- 0028201834
- -306
- Y. Matsumura Y.-I. Takeshima H. Okita Bull. Chem. Soc. Jpn. 1994 67 304 306
- (1994) Bull. Chem. Soc. Jpn. , vol.67 , pp. 304
- Matsumura, Y.¹ Takeshima, Y.-I.² Okita, H.³

51
- 18344396963
- -1390
- M. A. Letavic, et al. Bioorg. Med. Chem. Lett. 2002 12 1387 1390
- (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 1387
- Letavic Et Al., M.A.¹

52
- 0028955861
- M. Ito K.-i. Koyakumaru T. Ohta H. Takaya Synthesis 1995 376 378
- (1995) Synthesis , pp. 376-378
- Ito, M.¹ Koyakumaru, K.-I.² Ohta, T.³ Takaya, H.⁴

53
- 0035833681
- -2484
- J. A. Gómez-Vidal R. B. Silverman Org. Lett. 2001 3 2481 2484
- (2001) Org. Lett. , vol.3 , pp. 2481
- Gómez-Vidal, J.A.¹ Silverman, R.B.²

54
- 0000735249
- -3805
- K. Feichtinger C. Zapf H. L. Sings M. Goodman J. Org. Chem. 1998 63 3804 3805
- (1998) J. Org. Chem. , vol.63 , pp. 3804
- Feichtinger, K.¹ Zapf, C.² Sings, H.L.³ Goodman, M.⁴

55
- 0030936351
- -5304
- C. Levallet J. Lerpiniere S. Y. Ko Tetrahedron 1997 53 5291 5304
- (1997) Tetrahedron , vol.53 , pp. 5291
- Levallet, C.¹ Lerpiniere, J.² Ko, S.Y.³

56
- 0034640886
- -4622
- Y. Matsumura M. Inoue Y. Nakamura I. L. Talib T. Maki O. Onomura Tetrahedron Lett. 2000 41 4619 4622
- (2000) Tetrahedron Lett. , vol.41 , pp. 4619
- Matsumura, Y.¹ Inoue, M.² Nakamura, Y.³ Talib, I.L.⁴ Maki, T.⁵ Onomura, O.⁶

57
- 0025191219
- -685
- D. S. Bredt S. H. Snyder Proc. Natl. Acad. Sci. U. S. A. 1990 87 682 685
- (1990) Proc. Natl. Acad. Sci. U. S. A. , vol.87 , pp. 682
- Bredt, D.S.¹ Snyder, S.H.²

58
- 34247530882
- -1532
- Y. Chen J. A. Porco, Jr. J. S. Panek Org. Lett. 2007 9 1529 1532
- (2007) Org. Lett. , vol.9 , pp. 1529
- Chen, Y.¹ Porco Jr. J., A.² Panek, J.S.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.