Combinatorial organic synthesis using Parke-Davis's DIVERSOMER method

Accounts of Chemical Research

Volumn 29, Issue 3, 1996, Pages 114-122

  DeWitt, Sheila Hobbs ^{a,b,c,d,e,f,g}   Czarnik, Anthony W ^{a,h,i,j,k,l,m,n}  

^a PFIZER INC   (United States)

^b Department of Population Medicine and Diagnostic Sciences

^c DUKE UNIVERSITY   (United States)

^d FMC CORPORATION   (United States)

^e Med Chem Department at Parke Davis

^f BioOrganic Group

^g Diversomer Technologies Inc

^h UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

ⁱ Columbia University ^*

^j OHIO STATE UNIVERSITY   (United States)

^k Parke Davis Pharmaceutical Researc ^*

^l UNIVERSITY OF MICHIGAN   (United States)

^m UNIVERSITY OF TOLEDO   (United States)

ⁿ WAYNE STATE UNIVERSITY   (United States)

more..

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2842569383     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar950209v     Document Type: Article

References (40)

1. Hirschmann, R. Angew. Chem., Int. Ed. Engl. 1991, 30, 1278.
2. (a) Pirrung, M C. ChemTracts. Org. Chem. 1995, 8, 5
3. (b) Mitscher, L. A. ChemTracts. Org. Chem. 1995, 8, 19.
4. Czarnik, A. W ChemTracts: Org Chem. 1995, 8, 13.
5. In principle, the removal of either a solid or a liquid from a gas is even simpler, but we have not examined library generation schemes based on gaseous reagent delivery
6. SPOS can also be useful to selectively protect one end of a bifunctional starting material.
7. Merrifield, R B J. Am. Chem. Soc. 1963, 85, 2149.
8. Crowley, J. I., Rapoport, H. Acc. Chem. Res. 1976, 9, 135.
9. (a) Leznoff, C. C. Chem. Soc. Rev. 1974, 3, 65.
10. (b) Leznoff, C. C. Acc. Chem. Res. 1978, 11, 327.
11. For an early example, see. Epton, R.; Goddard, P.; Ivin, K. J. Polymer 1980, 21, 1367.
12. (a) DeWitt, S. H.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Cody, D. M R.; Pavia, M. R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909.
13. (b) DeWitt, S H; Schroeder, M. C; Stankovic, C. J; Strode, J. E., Czarnik, A. W. Drug Dev Res. 1994, 33, 116.
14. (c) DeWitt, S. H.; Kiely, J. S.; Pavia, M R.; Schroeder. M. C ; Stankovic, C. J. Apparatus for Multiple Simultaneous Synthesis. US 5,324,483, 1994
15. Look, G. C.; Holmes, C P ; Chinn, J P.; Gallop, M. A J. Org. Chem. 1994, 59, 7588.
16. Anderson, R. C., Stokes, J. P ; Shapiro, M. J Tetrahedron Lett. 1995, 36, 5311.
17. Crowley, J I ; Rapoport, H. J. Org. Chem 1980, 45, 3215.
18. Yan, B.; Kumaravel, G ; Anjaria, H., Wu, A ; Petter, R. C.; Jewell, C. F., Jr.; Wareing, J R J. Org Chem., in press.
19. Egner, B J ; Langley, G J.; Bradley, M J Org. Chem. 1995, 60, 2652
20. (a) MacDonald, A.; Halim, N.; DeWitt, S H.; Hogan, E.; Kieras, L ; Ghosh, S.; Ramage, R Parallel Purification and Resin By-Products in Solid Phase Synthesis. Presented at the 4th International Symposium on Solid Phase Synthesis, Edinburgh, Scotland, Sept 12, 1995.
21. (b) Halim, N.; DeWitt, S. H.; Hogan, E ; Kieras, L., Ghosh, S.; MacDonald, A.; Ramage, R. Parallel Purification and Resin By-Products in Solid Phase Synthesis Abstracts of Papers, 210th National Meeting of the American Chemical Society; American Chemical Society: Washington, DC, 1995; ORGN 267.
22. (a) Bunin, B A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997
23. (b) Bunin, B. A.; Plunkett, M. J.; Ellman, J A. Proc. Natl. Acad. Sci U.S.A. 1994, 91, 4708.
24. Houghten, R. A. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 5131.
25. ChemGlass, Inc., Vineland, NJ 08360.
26. DeWitt, S. H.; Czarnik, A. W. Curr. Opin. Biotechnol. 1995, 6, 640.
27. (a) Fawzi, M. B. In Advances in Laboratory Automation; Strimaitis, J. R., Little, J. N., Ed.; Zymark Corporation: Hopkington, MA, 1991; Vol. 7, pp 19-35.
28. (b) Strimaitis, J. R. J. Chem. Educ. 1989, 66, A13-A17.
29. Kramer, G. W.; Fuchs, P. L. In Advances in Laboratory Automation - Robotics 1985; Strimaitis, J. R., Hawk, G. L., Eds.; Zymark Corporation: Hopkington, MA, 1985; pp 417-429.
30. Lindsey, J. S. Chemom. Intell. Lab. Syst. 1992, 17, 15-45
31. Metivier, P.; Josses, P.; Bulliot, H.; Corbet, J. P.; Joux, B. Chemom. Intell. Lab Syst. 1992, 17, 137-43
32. Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367-383.
33. DeWitt, S. H ; Czarnik, A. W Curr. Opin. Biotechnol. 1995, 6, 640.
34. (a) Boojamra, C. G.; Burow, K. M ; Ellman, J. A J. Org. Chem. 1995, 60, 5742.
35. (b) Goff, D. A.; Zuckermann, R. N. J. Org. Chem. 1995, 60, 5744.
36. (c) Luth, J.; Rudolph-Bohner, S ; Moroder, L., Kolbeck, W.; Osapay, G., Goodman, M. A novel and facile route to benzodiazepine diversomers. Presented at the 14th American Peptide Symposium, Columbus, OH, June 1995.
37. Schroeder, M. C.; Kraker, A. J.; Moore, C. W.; Kiely, J. S.; DeWitt, S. H.; Czarnik, A. W. DIVERSOMER Technology: The Synthesis of Benzisothiazolones as Epidermal Growth Factor Receptor Tyrosine Kinase Inhibitors. Abstracts of Papers, 208th National Meeting of the American Chemical Society; American Chemical Society: Washington. DC, 1994, MEDI 239.
38. Ghosh, S.; DeWitt, S.; Hogan, E ; Mei, H ; Sanders, K.; Czarnik, A. W. Parallel Synthesis and Purification of Cyclic Dinucleotides Using Large-Scale, Semiautomated DIVERSOMER Technology. Submitted to J. Am. Chem. Soc.
39. MacDonald, A., DeWitt, S. H.; Hogan, E.; Ramage, R. Synthesis of Quinolone Antibiotics by DIVERSOMER Technology. Combinatorial Synthesis Symposium. Exeter, UK, July 20, 1995
40. DIVERSOMER is a registered trademark.