Synthetic receptors for uronic acid salts based on bicyclic guanidinium and deoxycholic acid subunits

Tetrahedron

Volumn 53, Issue 38, 1997, Pages 13119-13128

  Segura, Margot ^a   Alcázar, Victoria ^a   Prados, Pilar ^a   De Mendoza, Javier ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYCHOLIC ACID DERIVATIVE; DRUG RECEPTOR;

ARTICLE; COMPLEX FORMATION; DRUG SYNTHESIS; IN VITRO STUDY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; RECEPTOR BINDING;

EID: 0343924172     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00834-X     Document Type: Article

References (53)

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6. Rebek, J. Jr.; Nemeth, D.; Ballester, P.; Lin, F.-T. J. Am. Chem. Soc. 1987, 109, 3474. García-Tellado, F.; Goswami, S.; Chang, S.-K.; Geib, S. J.; Hamilton, A. D. ibid, 1990, 112, 7393. Galán, A.; de Mendoza, J.; Toiron, C.; Bruix, M.; Deslongchamps, G.; Rebek, J. Jr. ibid. 1991, 113, 9424. Hong, J.-I.; Namgoong, S. K.; Bernardi, A.; Still, W. C. ibid. 1991, 113, 5111. Alcázar, V.; Diederich, F. Angew. Chem . 1992, 104, 1503; Angew. Chem. Int. Ed. Engl. 1992, 31, 1521. Dhaenens, M.; Lehn, J.-M.; Vigneron, J. P. J. Chem. Soc., Perkin Trans. 2 1993, 1379. Peterson, B.; Diederich, F. Angew. Chem. 1994, 106, 1688; Angew. Chem. Int. Ed. Engl. 1994, 33, 1625. Reeder, J.; Castro, P. P.; Knobler, C. B.; Martinborough, E.; Owens, L.; Diederich, F. J. Org. Chem. 1994, 59, 3151. Eliseev, A. V.; Schneider, H.-J. J. Am. Chem. Soc. 1994, 116, 6081.
7. Rebek, J. Jr.; Nemeth, D.; Ballester, P.; Lin, F.-T. J. Am. Chem. Soc. 1987, 109, 3474. García-Tellado, F.; Goswami, S.; Chang, S.-K.; Geib, S. J.; Hamilton, A. D. ibid, 1990, 112, 7393. Galán, A.; de Mendoza, J.; Toiron, C.; Bruix, M.; Deslongchamps, G.; Rebek, J. Jr. ibid. 1991, 113, 9424. Hong, J.-I.; Namgoong, S. K.; Bernardi, A.; Still, W. C. ibid. 1991, 113, 5111. Alcázar, V.; Diederich, F. Angew. Chem . 1992, 104, 1503; Angew. Chem. Int. Ed. Engl. 1992, 31, 1521. Dhaenens, M.; Lehn, J.-M.; Vigneron, J. P. J. Chem. Soc., Perkin Trans. 2 1993, 1379. Peterson, B.; Diederich, F. Angew. Chem. 1994, 106, 1688; Angew. Chem. Int. Ed. Engl. 1994, 33, 1625. Reeder, J.; Castro, P. P.; Knobler, C. B.; Martinborough, E.; Owens, L.; Diederich, F. J. Org. Chem. 1994, 59, 3151. Eliseev, A. V.; Schneider, H.-J. J. Am. Chem. Soc. 1994, 116, 6081.
8. Rebek, J. Jr.; Nemeth, D.; Ballester, P.; Lin, F.-T. J. Am. Chem. Soc. 1987, 109, 3474. García-Tellado, F.; Goswami, S.; Chang, S.-K.; Geib, S. J.; Hamilton, A. D. ibid, 1990, 112, 7393. Galán, A.; de Mendoza, J.; Toiron, C.; Bruix, M.; Deslongchamps, G.; Rebek, J. Jr. ibid. 1991, 113, 9424. Hong, J.-I.; Namgoong, S. K.; Bernardi, A.; Still, W. C. ibid. 1991, 113, 5111. Alcázar, V.; Diederich, F. Angew. Chem . 1992, 104, 1503; Angew. Chem. Int. Ed. Engl. 1992, 31, 1521. Dhaenens, M.; Lehn, J.-M.; Vigneron, J. P. J. Chem. Soc., Perkin Trans. 2 1993, 1379. Peterson, B.; Diederich, F. Angew. Chem. 1994, 106, 1688; Angew. Chem. Int. Ed. Engl. 1994, 33, 1625. Reeder, J.; Castro, P. P.; Knobler, C. B.; Martinborough, E.; Owens, L.; Diederich, F. J. Org. Chem. 1994, 59, 3151. Eliseev, A. V.; Schneider, H.-J. J. Am. Chem. Soc. 1994, 116, 6081.
9. Rebek, J. Jr.; Nemeth, D.; Ballester, P.; Lin, F.-T. J. Am. Chem. Soc. 1987, 109, 3474. García-Tellado, F.; Goswami, S.; Chang, S.-K.; Geib, S. J.; Hamilton, A. D. ibid, 1990, 112, 7393. Galán, A.; de Mendoza, J.; Toiron, C.; Bruix, M.; Deslongchamps, G.; Rebek, J. Jr. ibid. 1991, 113, 9424. Hong, J.-I.; Namgoong, S. K.; Bernardi, A.; Still, W. C. ibid. 1991, 113, 5111. Alcázar, V.; Diederich, F. Angew. Chem . 1992, 104, 1503; Angew. Chem. Int. Ed. Engl. 1992, 31, 1521. Dhaenens, M.; Lehn, J.-M.; Vigneron, J. P. J. Chem. Soc., Perkin Trans. 2 1993, 1379. Peterson, B.; Diederich, F. Angew. Chem. 1994, 106, 1688; Angew. Chem. Int. Ed. Engl. 1994, 33, 1625. Reeder, J.; Castro, P. P.; Knobler, C. B.; Martinborough, E.; Owens, L.; Diederich, F. J. Org. Chem. 1994, 59, 3151. Eliseev, A. V.; Schneider, H.-J. J. Am. Chem. Soc. 1994, 116, 6081.
10. Rebek, J. Jr.; Nemeth, D.; Ballester, P.; Lin, F.-T. J. Am. Chem. Soc. 1987, 109, 3474. García-Tellado, F.; Goswami, S.; Chang, S.-K.; Geib, S. J.; Hamilton, A. D. ibid, 1990, 112, 7393. Galán, A.; de Mendoza, J.; Toiron, C.; Bruix, M.; Deslongchamps, G.; Rebek, J. Jr. ibid. 1991, 113, 9424. Hong, J.-I.; Namgoong, S. K.; Bernardi, A.; Still, W. C. ibid. 1991, 113, 5111. Alcázar, V.; Diederich, F. Angew. Chem . 1992, 104, 1503; Angew. Chem. Int. Ed. Engl. 1992, 31, 1521. Dhaenens, M.; Lehn, J.-M.; Vigneron, J. P. J. Chem. Soc., Perkin Trans. 2 1993, 1379. Peterson, B.; Diederich, F. Angew. Chem. 1994, 106, 1688; Angew. Chem. Int. Ed. Engl. 1994, 33, 1625. Reeder, J.; Castro, P. P.; Knobler, C. B.; Martinborough, E.; Owens, L.; Diederich, F. J. Org. Chem. 1994, 59, 3151. Eliseev, A. V.; Schneider, H.-J. J. Am. Chem. Soc. 1994, 116, 6081.
11. Rebek, J. Jr.; Nemeth, D.; Ballester, P.; Lin, F.-T. J. Am. Chem. Soc. 1987, 109, 3474. García-Tellado, F.; Goswami, S.; Chang, S.-K.; Geib, S. J.; Hamilton, A. D. ibid, 1990, 112, 7393. Galán, A.; de Mendoza, J.; Toiron, C.; Bruix, M.; Deslongchamps, G.; Rebek, J. Jr. ibid. 1991, 113, 9424. Hong, J.-I.; Namgoong, S. K.; Bernardi, A.; Still, W. C. ibid. 1991, 113, 5111. Alcázar, V.; Diederich, F. Angew. Chem . 1992, 104, 1503; Angew. Chem. Int. Ed. Engl. 1992, 31, 1521. Dhaenens, M.; Lehn, J.-M.; Vigneron, J. P. J. Chem. Soc., Perkin Trans. 2 1993, 1379. Peterson, B.; Diederich, F. Angew. Chem. 1994, 106, 1688; Angew. Chem. Int. Ed. Engl. 1994, 33, 1625. Reeder, J.; Castro, P. P.; Knobler, C. B.; Martinborough, E.; Owens, L.; Diederich, F. J. Org. Chem. 1994, 59, 3151. Eliseev, A. V.; Schneider, H.-J. J. Am. Chem. Soc. 1994, 116, 6081.
12. For sugar recognition see: Greenspoon, N.; Wachtel, E. J. Am. Chem. Soc. 1991, 113, 7233. Tsukagoshi, K.; Shinkai, S. J. Org. Chem. 1991, 56, 4089. Kobayashi, K.; Asakawa, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10307. Coterón, J. M.; Vicent, C.; Bosso, C.; Penadés, S. J. Am. Chem. Soc. 1993, 115, 10066. Das, G.; Hamilton, A. D. ibid 1994, 116, 11139. Cuntze, J.; Owens, L.; Alcázar, V.; Seiler, P.; Diederich, F. Helv. Chim. Acta 1995, 78, 367. Davis, A. P.; Menzer, S.; Walsh, J.J.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1996, 453.
13. For sugar recognition see: Greenspoon, N.; Wachtel, E. J. Am. Chem. Soc. 1991, 113, 7233. Tsukagoshi, K.; Shinkai, S. J. Org. Chem. 1991, 56, 4089. Kobayashi, K.; Asakawa, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10307. Coterón, J. M.; Vicent, C.; Bosso, C.; Penadés, S. J. Am. Chem. Soc. 1993, 115, 10066. Das, G.; Hamilton, A. D. ibid 1994, 116, 11139. Cuntze, J.; Owens, L.; Alcázar, V.; Seiler, P.; Diederich, F. Helv. Chim. Acta 1995, 78, 367. Davis, A. P.; Menzer, S.; Walsh, J.J.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1996, 453.
14. For sugar recognition see: Greenspoon, N.; Wachtel, E. J. Am. Chem. Soc. 1991, 113, 7233. Tsukagoshi, K.; Shinkai, S. J. Org. Chem. 1991, 56, 4089. Kobayashi, K.; Asakawa, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10307. Coterón, J. M.; Vicent, C.; Bosso, C.; Penadés, S. J. Am. Chem. Soc. 1993, 115, 10066. Das, G.; Hamilton, A. D. ibid 1994, 116, 11139. Cuntze, J.; Owens, L.; Alcázar, V.; Seiler, P.; Diederich, F. Helv. Chim. Acta 1995, 78, 367. Davis, A. P.; Menzer, S.; Walsh, J.J.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1996, 453.
15. For sugar recognition see: Greenspoon, N.; Wachtel, E. J. Am. Chem. Soc. 1991, 113, 7233. Tsukagoshi, K.; Shinkai, S. J. Org. Chem. 1991, 56, 4089. Kobayashi, K.; Asakawa, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10307. Coterón, J. M.; Vicent, C.; Bosso, C.; Penadés, S. J. Am. Chem. Soc. 1993, 115, 10066. Das, G.; Hamilton, A. D. ibid 1994, 116, 11139. Cuntze, J.; Owens, L.; Alcázar, V.; Seiler, P.; Diederich, F. Helv. Chim. Acta 1995, 78, 367. Davis, A. P.; Menzer, S.; Walsh, J.J.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1996, 453.
16. For sugar recognition see: Greenspoon, N.; Wachtel, E. J. Am. Chem. Soc. 1991, 113, 7233. Tsukagoshi, K.; Shinkai, S. J. Org. Chem. 1991, 56, 4089. Kobayashi, K.; Asakawa, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10307. Coterón, J. M.; Vicent, C.; Bosso, C.; Penadés, S. J. Am. Chem. Soc. 1993, 115, 10066. Das, G.; Hamilton, A. D. ibid 1994, 116, 11139. Cuntze, J.; Owens, L.; Alcázar, V.; Seiler, P.; Diederich, F. Helv. Chim. Acta 1995, 78, 367. Davis, A. P.; Menzer, S.; Walsh, J.J.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1996, 453.
17. For sugar recognition see: Greenspoon, N.; Wachtel, E. J. Am. Chem. Soc. 1991, 113, 7233. Tsukagoshi, K.; Shinkai, S. J. Org. Chem. 1991, 56, 4089. Kobayashi, K.; Asakawa, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10307. Coterón, J. M.; Vicent, C.; Bosso, C.; Penadés, S. J. Am. Chem. Soc. 1993, 115, 10066. Das, G.; Hamilton, A. D. ibid 1994, 116, 11139. Cuntze, J.; Owens, L.; Alcázar, V.; Seiler, P.; Diederich, F. Helv. Chim. Acta 1995, 78, 367. Davis, A. P.; Menzer, S.; Walsh, J.J.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1996, 453.
18. For sugar recognition see: Greenspoon, N.; Wachtel, E. J. Am. Chem. Soc. 1991, 113, 7233. Tsukagoshi, K.; Shinkai, S. J. Org. Chem. 1991, 56, 4089. Kobayashi, K.; Asakawa, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10307. Coterón, J. M.; Vicent, C.; Bosso, C.; Penadés, S. J. Am. Chem. Soc. 1993, 115, 10066. Das, G.; Hamilton, A. D. ibid 1994, 116, 11139. Cuntze, J.; Owens, L.; Alcázar, V.; Seiler, P.; Diederich, F. Helv. Chim. Acta 1995, 78, 367. Davis, A. P.; Menzer, S.; Walsh, J.J.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1996, 453.
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