Solution-phase synthesis of a β-amino alcohol combinatorial library

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 12, 1997, Pages 1511-1514

  Chng, Bee Lee ^a   Ganesan, Arasu ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL;

ARTICLE; DRUG SCREENING; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; MASS SPECTROMETRY; METHODOLOGY; THIN LAYER CHROMATOGRAPHY;

EID: 0030927125     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00260-6     Document Type: Article

References (17)

1. For excellent reviews, see inter alia: Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2289; Acc. Chem. Res. 1996, 29, issue #3; Bioorg. Med. Chem. 1996, 4, issue #5.
2. For excellent reviews, see inter alia: Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2289; Acc. Chem. Res. 1996, 29, issue #3; Bioorg. Med. Chem. 1996, 4, issue #5.
3. For excellent reviews, see inter alia: Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2289; Acc. Chem. Res. 1996, 29, issue #3; Bioorg. Med. Chem. 1996, 4, issue #5.
4. For examples, see: Smith, P. W.; Lai, J. Y. Q.; Whittington, A. R.; Cox, B.; Houston, J. G.; Stylli, C. H.; Banks, M. N.; Tiller, P. R. Bioorg. Med. Chem. Lett. 1994, 4, 2821; Carell, T.; Wintner, E. A.; Sutherland, A. J.; Rebek, J.; Dunayevskiy, Y. M.; Vouros, P. Chem. & Biol. 1995, 2, 171; Pirrung, M. C.; Chen, J. J. Am. Chem. Soc. 1995, 117, 1240; Cheng, S.; Comer, D. D.; Williams, J. P.; Myers, P. L.; Boger, D. L.; J. Am. Chem. Soc. 1996, 118, 2567; Storer, R. Drug Discovery Today 1996, 1, 248; Bailey, N.; Dean, A. W.; Judd, D. B.; Middlemiss, D.; Storer, R.; Watson, S. P. Bioorg. Med. Chem. Lett. 1996, 6, 1409.
5. For examples, see: Smith, P. W.; Lai, J. Y. Q.; Whittington, A. R.; Cox, B.; Houston, J. G.; Stylli, C. H.; Banks, M. N.; Tiller, P. R. Bioorg. Med. Chem. Lett. 1994, 4, 2821; Carell, T.; Wintner, E. A.; Sutherland, A. J.; Rebek, J.; Dunayevskiy, Y. M.; Vouros, P. Chem. & Biol. 1995, 2, 171; Pirrung, M. C.; Chen, J. J. Am. Chem. Soc. 1995, 117, 1240; Cheng, S.; Comer, D. D.; Williams, J. P.; Myers, P. L.; Boger, D. L.; J. Am. Chem. Soc. 1996, 118, 2567; Storer, R. Drug Discovery Today 1996, 1, 248; Bailey, N.; Dean, A. W.; Judd, D. B.; Middlemiss, D.; Storer, R.; Watson, S. P. Bioorg. Med. Chem. Lett. 1996, 6, 1409.
6. For examples, see: Smith, P. W.; Lai, J. Y. Q.; Whittington, A. R.; Cox, B.; Houston, J. G.; Stylli, C. H.; Banks, M. N.; Tiller, P. R. Bioorg. Med. Chem. Lett. 1994, 4, 2821; Carell, T.; Wintner, E. A.; Sutherland, A. J.; Rebek, J.; Dunayevskiy, Y. M.; Vouros, P. Chem. & Biol. 1995, 2, 171; Pirrung, M. C.; Chen, J. J. Am. Chem. Soc. 1995, 117, 1240; Cheng, S.; Comer, D. D.; Williams, J. P.; Myers, P. L.; Boger, D. L.; J. Am. Chem. Soc. 1996, 118, 2567; Storer, R. Drug Discovery Today 1996, 1, 248; Bailey, N.; Dean, A. W.; Judd, D. B.; Middlemiss, D.; Storer, R.; Watson, S. P. Bioorg. Med. Chem. Lett. 1996, 6, 1409.
7. For examples, see: Smith, P. W.; Lai, J. Y. Q.; Whittington, A. R.; Cox, B.; Houston, J. G.; Stylli, C. H.; Banks, M. N.; Tiller, P. R. Bioorg. Med. Chem. Lett. 1994, 4, 2821; Carell, T.; Wintner, E. A.; Sutherland, A. J.; Rebek, J.; Dunayevskiy, Y. M.; Vouros, P. Chem. & Biol. 1995, 2, 171; Pirrung, M. C.; Chen, J. J. Am. Chem. Soc. 1995, 117, 1240; Cheng, S.; Comer, D. D.; Williams, J. P.; Myers, P. L.; Boger, D. L.; J. Am. Chem. Soc. 1996, 118, 2567; Storer, R. Drug Discovery Today 1996, 1, 248; Bailey, N.; Dean, A. W.; Judd, D. B.; Middlemiss, D.; Storer, R.; Watson, S. P. Bioorg. Med. Chem. Lett. 1996, 6, 1409.
8. For examples, see: Smith, P. W.; Lai, J. Y. Q.; Whittington, A. R.; Cox, B.; Houston, J. G.; Stylli, C. H.; Banks, M. N.; Tiller, P. R. Bioorg. Med. Chem. Lett. 1994, 4, 2821; Carell, T.; Wintner, E. A.; Sutherland, A. J.; Rebek, J.; Dunayevskiy, Y. M.; Vouros, P. Chem. & Biol. 1995, 2, 171; Pirrung, M. C.; Chen, J. J. Am. Chem. Soc. 1995, 117, 1240; Cheng, S.; Comer, D. D.; Williams, J. P.; Myers, P. L.; Boger, D. L.; J. Am. Chem. Soc. 1996, 118, 2567; Storer, R. Drug Discovery Today 1996, 1, 248; Bailey, N.; Dean, A. W.; Judd, D. B.; Middlemiss, D.; Storer, R.; Watson, S. P. Bioorg. Med. Chem. Lett. 1996, 6, 1409.
9. For examples, see: Smith, P. W.; Lai, J. Y. Q.; Whittington, A. R.; Cox, B.; Houston, J. G.; Stylli, C. H.; Banks, M. N.; Tiller, P. R. Bioorg. Med. Chem. Lett. 1994, 4, 2821; Carell, T.; Wintner, E. A.; Sutherland, A. J.; Rebek, J.; Dunayevskiy, Y. M.; Vouros, P. Chem. & Biol. 1995, 2, 171; Pirrung, M. C.; Chen, J. J. Am. Chem. Soc. 1995, 117, 1240; Cheng, S.; Comer, D. D.; Williams, J. P.; Myers, P. L.; Boger, D. L.; J. Am. Chem. Soc. 1996, 118, 2567; Storer, R. Drug Discovery Today 1996, 1, 248; Bailey, N.; Dean, A. W.; Judd, D. B.; Middlemiss, D.; Storer, R.; Watson, S. P. Bioorg. Med. Chem. Lett. 1996, 6, 1409.
10. The β-amino alcohol functional group is present in many pharmacologically active molecules.
11. For a review, see: Smith, J. G. Synthesis 1984, 629.
12. Posner, G. H.; Rogers, D. Z. J. Am. Chem. Soc. 1977, 99, 8208.
13. Chini, M.; Crotti, P.; Macchia, F. J. Org. Chem. 1991, 56, 5939.
14. Recently, lanthanide triflates were also reported to be efficient catalysts for aminolysis of epoxides: Chini, M.; Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 433; Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc. Perkin Trans I 1994, 2597.
15. Recently, lanthanide triflates were also reported to be efficient catalysts for aminolysis of epoxides: Chini, M.; Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 433; Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc. Perkin Trans I 1994, 2597.
16. N1 pathway is favoured.
17. Notable exceptions were epoxides derived from medium-sized cycloalkenes e.g. cyclooctene oxide and caryophyllene oxide. Similar observations on lack of reactivity were noted in reference 5.