A convenient semicarbazide resin for the solid-phase synthesis of peptide ketones and aldehydes

Tetrahedron Letters

Volumn 47, Issue 10, 2006, Pages 1657-1661

  Vázquez, Jesús ^a   Albericio, Fernando ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Amino ketones; Combinatorial chemistry; High throughput synthesis; Ketone synthesis; Solid phase peptide synthesis

Indexed keywords

ALDEHYDE; CASPASE; CYSTEINE PROTEINASE INHIBITOR; FLUOROKETONE; HYDRAZINE; KETONE; POLYSTYRENE DERIVATIVE; RESIN; SEMICARBAZIDE; UNCLASSIFIED DRUG;

ARTICLE; COLORIMETRY; CROSS LINKING; DRUG EFFICACY; DRUG MECHANISM; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; PURIFICATION; SOLID PHASE SYNTHESIS;

EID: 31944443876     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.12.101     Document Type: Article

References (46)

1. H.-H. Otto, and T. Schirmeister Chem. Rev. 97 1997 133 171
2. J.H. McKerrow, and M.N.G. James Perspect. Drug Discov. Des. 6 1996 1 125
3. T. Groth, and M. Meldal J. Comb. Chem. 3 2001 45 63
4. G. Semple, D.M. Ashworth, A.R. Batt, A.J. Baxter, D.W.M. Benzies, L.H. Elliot, D.M. Evans, R.J. Franklin, P. Hudson, P.D. Jenkins, G.R. Pitt, D.P. Rooker, S. Yamamoto, and Y. Isomura Bioorg. Med. Chem. Lett. 8 1998 959 964
5. T. Yasuma, S. Oi, N. Choh, T. Nomura, N. Furuyama, A. Nishimura, Y. Fujisawa, and T. Sohda J. Med. Chem. 41 1998 4301 4308
6. T.S. Morris, S. Frormann, S. Sheckosky, C. Lowe, M.S. Lall, V. Gauss-Müller, R.H. Purcell, S.U. Emerson, J.C. Vederas, and B.A. Malcolm Bioorg. Med. Chem. 5 1997 797 807
7. J.T. Palmer, D. Rasnick, J. Klaus, and D. Brömme J. Med. Chem. 38 1995 3193 3196
8. A.M. Mjalli, K.T. Chapman, J.J. Zhao, N.A. Thornberry, E.P. Peterson, and M. MacCoss Bioorg. Med. Chem. Lett. 5 1995 1405 1408
9. N.A. Thornberry, and Y. Lazebnick Science 281 1998 1312 1316
10. C.B. Hurelbrink, R.J.E. Armstrong, L.M. Luheshi, S.B. Dunnett, A.E. Rosser, and R.A. Barker Exp. Neurol. 171 2001 46 58
11. D. Lee, S.A. Long, J.H. Murray, J.L. Adams, M.E. Nuttall, D.P. Nadeau, K. Kikly, J.D. Winkler, C.-M. Sung, M.D. Ryan, M.A. Levy, P.M. Keller, and W.E. DeWolf J. Med. Chem. 44 2001 2015 2026
12. N.A. Thornberry, T.A. Rano, E.P. Peterson, D.M. Rasper, T. Timkey, M. García-Calvo, V.M. Houtzager, P.A. Nordstrom, S. Roy, J.P. Vaillancourt, K.T. Chapman, and D.W. Nicholson J. Biol. Chem. 272 1997 17907 17911
13. M. García-Calvo, E.P. Peterson, B. Leiting, R. Ruel, D.W. Nicholson, and N.A. Thornberry J. Biol. Chem. 273 1998 32608 32613
14. I.C. Choong, W. Lew, D. Lee, P. Pham, M.T. Burdett, J.W. Lam, C. Wiesmann, T.N. Luong, B. Fahr, W.L. DeLano, R.S. McDowell, D.A. Allen, D.A. Erlanson, E.M. Gordon, and T. O'Brien J. Med. Chem. 45 2002 5005 5022
15. R. Fattorusso, D. Jung, K.J. Crowell, M. Forino, and M. Pellecchia J. Med. Chem. 48 2005 1649 1656
16. J. Vazquez, and F. Albericio Tetrahedron Lett. 43 2002 7499 7502
17. A.K. Sharma, and P.J. Hergenrother Org. Lett. 5 2003 2107 2109
18. T.A. Rano, T. Timkey, E.P. Peterson, J. Rotonda, D.W. Nicholson, J.W. Becker, K.T. Chapman, and N.A. Thornberry Chem. Biol. 4 1997 149 155
19. V. Bertini, F. Lucchesini, M. Pocci, and A. De Munno Tetrahedron Lett. 39 1998 9263 9266
20. S. Chamoin, S. Houldsworth, C.G. Kruse, W.I. Bakker, and V. Snieckus Tetrahedron Lett. 39 1998 4179 4182
21. M.E. Fraley, and R.S. Rubino Tetrahedron Lett. 38 1997 3365 3368
22. N.W. HirdKazuyuki, K. Irie, and K. Nagai Tetrahedron Lett. 38 1997 7111 7114
23. A.M. Murphy, R. Dagnino, P.L. Vallar, A.J. Trippe, S.L. Sherman, R.H. Lumpkin, S.Y. Tamura, and T.R. Webb J. Am. Chem. Soc. 114 1992 3156 3157
24. M.-A. Poupart, G. Fazal, S. Goulet, and L.T. Mar J. Org. Chem. 64 1999 1356 1361
25. Selected examples of patents where it is used the hydrazine-based linkage: WO00/23421 Idun Pharmaceuticals, Inc.
26. WO01/27085 Merck Frosst Canada & Co.
27. WO03/024955 Sunesis Pharmaceuticals, Inc.
28. R. Lazny, and M. Michalak Synlett 11 2002 1931 1934
29. R. Lazny, A. Nodzewska, and K. Wolosewicz Synthesis 18 2003 2858 2864
30. S.D. Lepore, and M.R. Wiley Org. Lett. 5 2003 7 10
31. M. Zhu, E. Ruijter, and L.A. Wessjohann Org. Lett. 6 2004 3921 3924
32. R. Lazny, A. Nodzewska, M. Sienkiewicz, and K. Wolosewicz J. Comb. Chem. 7 2005 109 116
33. A. Lee, L. Huang, and J.A. Ellman J. Am. Chem. Soc. 121 1999 9907 9914
34. W.J. Wood, L. Huang, and J.A. Ellman J. Comb. Chem. 5 2003 869 880
35. Y. Han, A. Giroux, E.L. Grimm, R. Aspiotis, S. Francoeur, C.I. Bayly, D.J. Mckay, S. Roy, S. Xanthoudakis, J.P. Vaillancourt, D.M. Rasper, J. Tam, P. Tawa, N.A. Thornberry, E.P. Paterson, M. García-Calvo, J.W. Becker, J. Rotonda, D.W. Nicholson, and R.J. Zamboni Bioorg. Med. Chem. Lett. 14 2004 805 808
36. E.L. Grimm, B. Roy, R. Aspiotis, C.I. Bayly, D.W. Nicholson, D.M. Rasper, J. Renaud, S. Roy, J. Tam, P. Tawa, J.P. Vaillancourt, S. Xanthoudakis, and R.J. Zamboni Bioorg. Med. Chem. 12 2004 845 851
37. D. Kato, K.M. Boatright, A.B. Berger, T. Nazif, G. Blum, C. Ryan, K.A.H. Chehade, G.S. Salvesen, and M. Bogyo Nature Chem. Biol. 1 2005 33 38
38. J. Alsina, C. Chiva, M. Ortiz, F. Rabanal, E. Giralt, and F. Albericio Tetrahedron Lett. 38 1997 883 886
39. J. Alsina, F. Rabanal, C. Chiva, E. Giralt, and F. Albericio Tetrahedron 54 1998 10125 10152
40. P. Romanovskis, and A.F. Spatola J. Pept. Res. 52 1998 356 374
41. J. Vazquez, G.Y. Qushair, and F. Albericio Method. Enzymol. 369 2003 21 35
42. The discrepancies between the results shown in this work and those reported by Ellman (see Ref. 16) could be due to the use of a polystyrene resin instead of the most expensive ArgoGel and to the lower nucleophilicity of a benzyl alcohol (polystyrene resin) in front of a hydroxymethyl (ArgoGel).
43. F. Yraola, R. Ventura, M. Vendrell, A. Colombo, J.-C. Fernandez, N. De La Figuera, D. Fernandez-Forner, M. Royo, P. Forns, and F. Albericio QSAR Combinat. Sci. 23 2004 145 152
44. W.S. Hancock, and J.E. Battersby Anal. Biochem. 71 1976 260 264
45. M. García-Calvo, E.P. Peterson, B. Leiting, R. Ruel, D.W. Nicholson, and N.A. Thornberry J. Biol. Chem. 273 1998 32608 32613
46. T.A. Rano, T. Timkey, E.P. Peterson, J. Rotonda, D.W. Nicholson, J.W. Beckeer, K.T. Chapman, and N.A. Thornberry Chem. Biol. 4 1997 149 155