Solution-phase generation of tetraurea libraries

Bioorganic and Medicinal Chemistry

Volumn 4, Issue 5, 1996, Pages 655-657

  Shipps Jr , Gerald W ^a   Spitz, Urs P ^a   Rebek Jr , Julius ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Chlorocatecholborane; Isocyanates; Solution phase combinatorial chemistry; Ureas

Indexed keywords

UREA DERIVATIVE; XANTHENE DERIVATIVE;

CONFERENCE PAPER; DRUG DESIGN; DRUG PURITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; TECHNIQUE;

EID: 0029895415     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/0968-0896(96)00059-4     Document Type: Conference Paper

References (16)

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3. Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1994, 116, 11171. Burgess, K.; Linthicum, D. S.; Shin, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 907. Gordon, D. W.; Steele, J. Bioorg. Med. Chem. Lett. 1995, 5, 47.
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5. Problems with unwanted hydrolysis and low bioavailability of peptides has stimulated development of more stable analogs. Chorev, M.; Goodman, M. Acc. Chem. Res. 1993, 26, 266. DeWitt, S. H.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Reynolds Cody, D. M.; Pavia, M. R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909. Peisach, E.; Casebier, D.; Gallion, S. L.; Furth, P.; Petsko, G. A.; Hogan, J. C., Jr.; Ringe, D. Science 1995, 269, 66.
6. Problems with unwanted hydrolysis and low bioavailability of peptides has stimulated development of more stable analogs. Chorev, M.; Goodman, M. Acc. Chem. Res. 1993, 26, 266. DeWitt, S. H.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Reynolds Cody, D. M.; Pavia, M. R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909. Peisach, E.; Casebier, D.; Gallion, S. L.; Furth, P.; Petsko, G. A.; Hogan, J. C., Jr.; Ringe, D. Science 1995, 269, 66.
7. Problems with unwanted hydrolysis and low bioavailability of peptides has stimulated development of more stable analogs. Chorev, M.; Goodman, M. Acc. Chem. Res. 1993, 26, 266. DeWitt, S. H.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Reynolds Cody, D. M.; Pavia, M. R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909. Peisach, E.; Casebier, D.; Gallion, S. L.; Furth, P.; Petsko, G. A.; Hogan, J. C., Jr.; Ringe, D. Science 1995, 269, 66.
8. Lam, Y. S. P.; Jadhav, P. K.; Eyermann, C. J.; Hodge, C. N.; Ru, Y.; Bacheler, L. T.; Meek, J. L.; Otto, M. J.; Rayner, M. M.; Wong, Y. N.; Chang, C.-H.; Weber, P. C.; Jackson, D. A.; Sharpe, T. R.; Erickson-Viitanen, S. Science 1994, 263, 380.
9. Davidson, E.; Shipps, G. W.; Spitz, U. P.; Rebek, J. Jr., Unpublished results.
10. For a review of isocyanate chemistry, see: Ozaki, S. Chem. Rev. 1972, 72, 457.
11. Kricheldorf, H. R. Synlett 1972, 551.
12. March, J. Advanced Organic Chemistry, 4th ed.; John Wiley & Sons: New York, 1992; pp 1091-1092.
13. Valli, V. L. K.; Alper, H. J. Org. Chem. 1995, 60, 257-258.
14. 8 (M + H), 955.5141; found, 955.5115.
15. To 50 mg of library material was added 3 mL of TFA. The yellow solution was stirred for 1 h (fine bubbles observed); then coned to a yellow, hygroscopic foam. When ether:hexane (1:1) (2 mL) was added, an off-white powder precipitated. NMR spectroscopy verified that no t-butyl groups remained attached to the core structures.
16. Isocyanates react with formamides, but only under extreme conditions: Weiner, M. L. J. Org. Chem. 1960, 25, 2245.