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Volumn 39, Issue 33, 1998, Pages 6083-6086

The 'triamino-analogue' of methyl cholate; A facial amphiphile and scaffold with potential for combinatorial and molecular recognition chemistry

Author keywords

[No Author keywords available]

Indexed keywords

CHOLIC ACID DERIVATIVE;

EID: 0032514572     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01254-4     Document Type: Article
Times cited : (48)

References (30)
  • 1
    • 0000759694 scopus 로고    scopus 로고
    • 1. Reviews: Davis, A. P. Chem. Soc. Rev. 1993, 22, 243; Davis, A. P.; Bonar-Law, R. P.; Sanders, J. K. M. in Comprehensive Supramolecular Chemistry; Murakami, Y., Ed.; Pergamon: Oxford, 1996; Vol. 4, p 257; Walliman, P.; Marti, T.; Furer, A.; Diederich, F. Chem. Rev, 1997, 97, 1567; Li, Y. X.; Dias, J. R. Chem. Rev. 1997, 97, 283.
    • (1993) Chem. Soc. Rev. , vol.22 , pp. 243
    • Davis, A.P.1
  • 2
    • 0000759694 scopus 로고    scopus 로고
    • Murakami, Y., Ed.; Pergamon: Oxford
    • 1. Reviews: Davis, A. P. Chem. Soc. Rev. 1993, 22, 243; Davis, A. P.; Bonar-Law, R. P.; Sanders, J. K. M. in Comprehensive Supramolecular Chemistry; Murakami, Y., Ed.; Pergamon: Oxford, 1996; Vol. 4, p 257; Walliman, P.; Marti, T.; Furer, A.; Diederich, F. Chem. Rev, 1997, 97, 1567; Li, Y. X.; Dias, J. R. Chem. Rev. 1997, 97, 283.
    • (1996) Comprehensive Supramolecular Chemistry , vol.4 , pp. 257
    • Davis, A.P.1    Bonar-Law, R.P.2    Sanders, J.K.M.3
  • 3
    • 0001593086 scopus 로고    scopus 로고
    • 1. Reviews: Davis, A. P. Chem. Soc. Rev. 1993, 22, 243; Davis, A. P.; Bonar-Law, R. P.; Sanders, J. K. M. in Comprehensive Supramolecular Chemistry; Murakami, Y., Ed.; Pergamon: Oxford, 1996; Vol. 4, p 257; Walliman, P.; Marti, T.; Furer, A.; Diederich, F. Chem. Rev, 1997, 97, 1567; Li, Y. X.; Dias, J. R. Chem. Rev. 1997, 97, 283.
    • (1997) Chem. Rev. , vol.97 , pp. 1567
    • Walliman, P.1    Marti, T.2    Furer, A.3    Diederich, F.4
  • 4
    • 0000097162 scopus 로고    scopus 로고
    • 1. Reviews: Davis, A. P. Chem. Soc. Rev. 1993, 22, 243; Davis, A. P.; Bonar-Law, R. P.; Sanders, J. K. M. in Comprehensive Supramolecular Chemistry; Murakami, Y., Ed.; Pergamon: Oxford, 1996; Vol. 4, p 257; Walliman, P.; Marti, T.; Furer, A.; Diederich, F. Chem. Rev, 1997, 97, 1567; Li, Y. X.; Dias, J. R. Chem. Rev. 1997, 97, 283.
    • (1997) Chem. Rev. , vol.97 , pp. 283
    • Li, Y.X.1    Dias, J.R.2
  • 8
    • 0030906528 scopus 로고    scopus 로고
    • Ref. 1d contains a preliminary mention of N-protected 2, as a starting material for a potent electroneutral anionophore
    • (d) Davis, A. P.; Perry, J. J.; Williams, R. P. J. Am. Chem. Soc. 1997, 119, 1793. Ref. 1d contains a preliminary mention of N-protected 2, as a starting material for a potent electroneutral anionophore.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 1793
    • Davis, A.P.1    Perry, J.J.2    Williams, R.P.3
  • 15
    • 0010519947 scopus 로고    scopus 로고
    • note
    • 4. Cf. the secondary hydroxyl groups in 1 which are not, by themselves, sufficiently hydrophilic to promote solubility in water. See discussion later in the text.
  • 18
    • 0010520871 scopus 로고    scopus 로고
    • note
    • 7. While both 3α and 7β positions are equatorial, it seems that the former is slightly more exposed. A small amount of diol formed by over-reaction could be bis-acetylated for recycling.
  • 19
    • 0026045538 scopus 로고
    • 8. For previous work on the reduction of steroidal oximes, see refs. 1c, 3b and: Schneider, S.; Schramm, U.; Schreyer, A.; Buscher, H.-P.; Gerok, W.; Kurz, G. J. Lipid Res. 1991, 32, 1755; Ahmed, S.; Alauddin, M.; Caddy, B.; Smith, M. M.; Sidwell, W. T. L. Aust. J. Chem. 1971, 24, 521; Sato, Y. Bull. Chem. Soc. Japan 1965, 38, 1581; Guthrie, J. P. Can. J. Chem. 1972, 50, 3993.
    • (1991) J. Lipid Res. , vol.32 , pp. 1755
    • Schneider, S.1    Schramm, U.2    Schreyer, A.3    Buscher, H.-P.4    Gerok, W.5    Kurz, G.6
  • 20
    • 84971020080 scopus 로고
    • 8. For previous work on the reduction of steroidal oximes, see refs. 1c, 3b and: Schneider, S.; Schramm, U.; Schreyer, A.; Buscher, H.-P.; Gerok, W.; Kurz, G. J. Lipid Res. 1991, 32, 1755; Ahmed, S.; Alauddin, M.; Caddy, B.; Smith, M. M.; Sidwell, W. T. L. Aust. J. Chem. 1971, 24, 521; Sato, Y. Bull. Chem. Soc. Japan 1965, 38, 1581; Guthrie, J. P. Can. J. Chem. 1972, 50, 3993.
    • (1971) Aust. J. Chem. , vol.24 , pp. 521
    • Ahmed, S.1    Alauddin, M.2    Caddy, B.3    Smith, M.M.4    Sidwell, W.T.L.5
  • 21
    • 0013805653 scopus 로고
    • 8. For previous work on the reduction of steroidal oximes, see refs. 1c, 3b and: Schneider, S.; Schramm, U.; Schreyer, A.; Buscher, H.-P.; Gerok, W.; Kurz, G. J. Lipid Res. 1991, 32, 1755; Ahmed, S.; Alauddin, M.; Caddy, B.; Smith, M. M.; Sidwell, W. T. L. Aust. J. Chem. 1971, 24, 521; Sato, Y. Bull. Chem. Soc. Japan 1965, 38, 1581; Guthrie, J. P. Can. J. Chem. 1972, 50, 3993.
    • (1965) Bull. Chem. Soc. Japan , vol.38 , pp. 1581
    • Sato, Y.1
  • 22
    • 0000181014 scopus 로고
    • 8. For previous work on the reduction of steroidal oximes, see refs. 1c, 3b and: Schneider, S.; Schramm, U.; Schreyer, A.; Buscher, H.-P.; Gerok, W.; Kurz, G. J. Lipid Res. 1991, 32, 1755; Ahmed, S.; Alauddin, M.; Caddy, B.; Smith, M. M.; Sidwell, W. T. L. Aust. J. Chem. 1971, 24, 521; Sato, Y. Bull. Chem. Soc. Japan 1965, 38, 1581; Guthrie, J. P. Can. J. Chem. 1972, 50, 3993.
    • (1972) Can. J. Chem. , vol.50 , pp. 3993
    • Guthrie, J.P.1
  • 23
    • 0026767678 scopus 로고
    • 9. For related conversions, see: Davis, A. P.; Orchard, M. G. Tetrahedron Lett. 1992, 33, 5111; Davis, A. P.; Dresen, S.; Lawless, L. J. Tetrahedron Lett. 1997, 38, 4305.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 5111
    • Davis, A.P.1    Orchard, M.G.2
  • 24
    • 0030919027 scopus 로고    scopus 로고
    • 9. For related conversions, see: Davis, A. P.; Orchard, M. G. Tetrahedron Lett. 1992, 33, 5111; Davis, A. P.; Dresen, S.; Lawless, L. J. Tetrahedron Lett. 1997, 38, 4305.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 4305
    • Davis, A.P.1    Dresen, S.2    Lawless, L.J.3
  • 25
    • 0010493397 scopus 로고    scopus 로고
    • note
    • 8 requires C, 67.09; H, 9.75; N, 5.72%.
  • 27
    • 0010519948 scopus 로고    scopus 로고
    • note
    • + at pH ~ 7.5-10. Precipitation was apparent at pH >9.5.
  • 29
    • 0028097350 scopus 로고
    • 14. Cf. the antibacterial effects of squalamine, and other amino-steroids: Moriarty, R. M.; Tuladhar, S. M.; Guo, L.; Wehrli, S. Tetrahedron Lett. 1994, 35, 8103; Sadownik, A.; Deng, G.; Janout, V.; Regen, S. L. J. Am. Chem. Soc. 1995, 117, 6138.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 8103
    • Moriarty, R.M.1    Tuladhar, S.M.2    Guo, L.3    Wehrli, S.4
  • 30
    • 0001366519 scopus 로고
    • 14. Cf. the antibacterial effects of squalamine, and other amino-steroids: Moriarty, R. M.; Tuladhar, S. M.; Guo, L.; Wehrli, S. Tetrahedron Lett. 1994, 35, 8103; Sadownik, A.; Deng, G.; Janout, V.; Regen, S. L. J. Am. Chem. Soc. 1995, 117, 6138.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 6138
    • Sadownik, A.1    Deng, G.2    Janout, V.3    Regen, S.L.4


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