Efficient parallel synthesis of macrocyclic peptidomimetics

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 16, 2008, Pages 4731-4735

  Marsault, Eric ^a   Hoveyda, Hamid R ^a   Gagnon, René ^a   Peterson, Mark L ^a   Vézina, Martin ^a   Saint Louis, Carl ^a   Landry, Annick ^a   Pinault, Jean François ^a   Ouellet, Luc ^a   Beauchemin, Sophie ^a   Beaubien, Sylvie ^a   Mathieu, Axel ^a   Benakli, Kamel ^a   Wang, Zhigang ^a   Brassard, Martin ^a   Lonergan, David ^a   Bilodeau, François ^a   Ramaseshan, Mahesh ^a   Fortin, Nadia ^a   Lan, Ruoxi ^a   Li, Shigui ^a   Galaud, Fabrice ^a   Plourde, Véronique ^a   Champagne, Manon ^a   Doucet, Annie ^a   Bhérer, Patrick ^a   Gauthier, Maude ^a   Olsen, Gilles ^a   Villeneuve, Gérald ^a   Bhat, Shridhar ^a   Foucher, Laurence ^a   Fortin, Daniel ^a   Peng, Xiaowen ^a   Bernard, Sylvain ^a   Drouin, Alexandre ^a   Déziel, Robert ^a   Berthiaume, Gilles ^a   Dory, Yves L ^a   Fraser, Graeme L ^a   Deslongchamps, Pierre ^a   more..

^a Tranzyme Pharma Inc   (Canada)

Author keywords

Macrocycle; Peptidomimetic; Solid phase synthesis; Tether

Indexed keywords

MACROCYCLIC COMPOUND;

ARTICLE; CONFORMATION; CYCLIZATION; SOLID PHASE SYNTHESIS;

CHEMISTRY, PHARMACEUTICAL; COMBINATORIAL CHEMISTRY TECHNIQUES; DIMERIZATION; DIPEPTIDES; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; PEPTIDES; PEPTIDES, CYCLIC; SILVER; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 48649104582     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.06.085     Document Type: Article

References (42)

1. Veber D.F., Johnson S.R., Cheng H.Y., Smith B.R., Ward K.W., and Kopple K.D. J. Med. Chem. 45 (2002) 2615
2. For selected examples in several therapeutic fields, see:. Veber D.F., Freidinger R.M., et al. Nature 292 (1981) 55
3. Shi Z.D., Lee K., Wei C.Q., Roberts L.R., Worthy K.M., Fisher R.J., and Burke R.R. J. Med. Chem. 47 (2004) 788
4. Lamarre D., Anderson P.C., et al. Nature 1 (2003)
5. Nantermet P.G., Barrow J.C., et al. Bioorg. Med. Chem. Lett. 13 (2003) 2781
6. Li P., and Roller P. Curr. Top. Med. Chem. 2 (2002) 325
7. Hruby V.J., Lu D., Sharma S.D., de la Castrucci A., Kesteron R.A., et al. J. Med. Chem. 38 (1995) 3454
8. Geary R.P., and Fairlie D.P. Curr. Opin. Drug Discov. Dev. 1 (1998) 208
9. Goodman M., and Ro S. Peptidomimetics for drug design. Burger's Medicinal Chemistry and Drug Discovery vol. 1 (1995), Wiley, New York 803-861
10. Kessler H. Angew. Chem., Int. Ed. Engl. 21 (1982) 512
11. For examples of parallel methods for the synthesis of macrocyclic peptides & peptidomimetics, see:. Barrett A.G.M., Hennessy A.J., Le Vézouët R., Procopiou P.A., Seale P.W., Stefaniak S., Upton R.J., White A.J.P., and Williams D.J. J. Org. Chem. 69 (2004) 1028
12. Lee D., Sello J.K., and Schreiber S.L.A. J. Am. Chem. Soc. 121 (1999) 10648
13. Jefferson E.A., Arakawa S., Blyn L.B., Miyaji A., Osgood S.A., Ranken R., Risen L.M., and Swayze E.E. J. Med. Chem. 45 (2002) 3430
14. Roberts K.D., and Ede N.J. J. Pept. Sci. 13 (2007) 811
15. Turner R.A., Oliver A.G., and Lokey R.S. Org. Lett. 9 (2007) 5011
16. Kohli R.M., Walsh C.T., and Burkart M.D. Nature 418 (2002) 658
17. Park C., and Burgess K. J. Comb. Chem. 3 (2001) 257
18. Horton D.A., Bourne G.T., and Smythe M.L. J. Comp. Aid. Mol. Des. 16 (2002) 415
19. On the properties of clinical candidate TZP-101 belonging to this class, see:. Venkova K., Fraser G., Hoveyda H.R., and Greenwood-van Meerveld B. Dig. Dis. Sci. 52 (2007) 2241
20. Lasseter K.C., Shaughnessy L., Cummings D., Pezzullo J.C., Wargin W., Gagnon R., Oliva J., and Kosutic G. J. Clin. Pharm. 48 (2008) 193
21. On the discovery of potent antagonists to the motilin receptor based on this class, see:. Marsault E., Hoveyda H.R., Peterson M.L., Saint-Louis C., Landry A., Vézina M., Ouellet L., Wang Z., Ramaseshan M., Beaubien S., Benakli K., Beauchemin S., Peeters T., Déziel R., and Fraser G. J. Med. Chem. 49 (2006) 7190
22. Marsault E., Hoveyda H.R., Peterson M.L., Saint-Louis C., Landry A., Vézina M., Ouellet L., Wang Z., Ramaseshan M., Beaubien S., Benakli K., Beauchemin S., Peeters T., Déziel R., and Fraser G. Bioorg. Med. Chem. Lett. 17 (2007) 4187
23. Birr C., Lochinger W., Stahnke G., and Lang P. Liebigs Ann. Chem. 763 (1972) 162
24. For selected examples of cyclative release using a variety of reactions, see:. Nicolaou K.C., Pastor J., Winssinger N., and Murphy F. J. Am. Chem. Soc. 120 (1998) 5132
25. Shigenaga A., Moss J.A., Ashley F.T., Kaufmann G.F., and Janda K.D. Synlett 4 (2006) 551
26. Pernerstorfer J., Schuster M., and Blechert S. Chem. Commun. (1997) 1949
27. Piscopio A.D., Miller J.F., and Koch K. Tetrahedron 55 (1999) 8189
28. Sasmal S., Geyer A., and Meier M. Eur. J. Org. Chem. 67 (2002) 6260
29. van Maarseveen J.H. Comb. Chem. High Throughput Screen 1 (1998) 185
30. Vedejs E., Lin S., Klapars A., and Wang J. J. Am. Chem. Soc. 118 (1996) 9796
31. Fukuyama T., Cheung M., Jow C.K., Hidai Y., and Kan T. Tetrahedron Lett. 38 (1997) 5831
32. Boddy C.N. Chem. Biol. 11 (2004) 1599
33. Dawson P.E., Muir T.W., Clark-Lewis I., and Kent S.B.H. Science 266 (1994) 776
34. Zhang L., and Tam J.P. J. Am. Chem. Soc. 121 (1999) 3311
35. Wuts P.G.M., Gu R.L., Northuis J.M., and Thomas C.L. Tetrahedron Lett. 39 (1998) 9155
36. The CLND (ChemiLuminescent Nitrogen Detection) detector allows for detection and quantification of nitrogen containing compounds specifically:. Fujinari E.M., and Manes J.D. J. Chrom. A 676 (1994) 113
37. Letot E., Koch G., Falchetto R., Bovermann G., Oberer L., and Roth H.-J. J. Comb. Chem. 7 (2005) 364
38. For information on loading calculations, please refer to supporting information.
39. Acp = 1-aminocyclopentanecarboxylic acid; 3-Thi = 3-thienlyalanine.
40. Look G.C., Murphy M.M., Campbell D.A., and Gallop M.A. Tetrahedron Lett. 36 (1995) 2937
41. Khan N.M., Arumugan V., and Balasubramanian S. Tetrahedron Lett. 37 (1996) 4819
42. Based on analysis of ca. 25 sequences, this observation turned out not to be general; data not shown.