Synthesis of 12-membered macrocyclic templates and library analogs for PPI

Tetrahedron Letters

Volumn 54, Issue 25, 2013, Pages 3298-3301

  Chen, Jinshan ^a   Rong, Frank ^b,c   Shan, Bo ^b   Chen, Yuanwei ^c   Li, Yingfu ^c   Yu, Hua ^c   Chen, Li ^c   Kuang, Tongtao ^c   Li, Shai ^c   Chen, Youpei ^c   Du, Jing ^c   Ai, Chaowu ^c   Li, Jian ^c   Li, Xiaoyong ^c   Shi, Changqing ^c   Jiang, Zhilong ^c   Long, Yuanqiang ^c   Gao, Qiu ^c   Wang, Zhibo ^c   Xu, Kexin ^c   Ran, Xin ^b   Yi, Hua ^b   Zhao, Dapeng ^b   Qiao, Hongyun ^b   Shen, Junwei ^b   Liu, Bo ^b   Liu, Chonggang ^b   Wu, Kai ^b   Geng, Xi ^b   Tan, Jieyang ^b   McLeod, Dale ^a   Frost, Heather ^a   Bai, Guoyun ^a   Goetz, Gilles ^a   Federico III, James ^a   Whitney Pickett, Carrie ^a   Troutman, Matthew ^a   Noe, Mark C ^a   Guimaraes, Cristiano ^a   Piotrowski, David W ^a   Magee, Thomas V ^a   more..

^a PFIZER INC   (United States)

^b Zhangjiang Hi Tech Park   (China)

^c ChemPartner   (China)

Author keywords

12 Membered ring; Intra molecular hydrogen bond; Lactam cyclization; Macrocyclization; Permeability

Indexed keywords

ARTICLE; CYCLIZATION; PROTEIN PROTEIN INTERACTION; PROTEIN STRUCTURE; PROTEIN SYNTHESIS;

EID: 84877833806     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.04.058     Document Type: Article

References (22)

1. J.C. Fuller, N.J. Burgoyne, and R.M. Jackson Drug Discovery Today 14 2009 155 161
2. D. Reichmann, O. Rahat, M. Cohen, H. Neuvirth, and G. Schreiber Curr. Opin. Struct. Biol. 17 2007 67 76
3. N. London, D. Movshovitz-Attias, and O. Schueler-Furman Structure 18 2010 188 199
4. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Adv. Drug Deliv. Rev. 23 1997 3 25
5. J.A. Wells, and C.L. McClendon Nature 450 2007 1001 1009
6. H. Yin, and A.D. Hamilton Angew. Chem., Int. Ed. 44 2005 4130 4163
7. M.R. Arkin, and J.A. Wells Nat. Rev. Drug Disc. 3 2004 301 317
8. L.O. Sillerud, and R.S. Larson Curr. Protein Pept. Sci. 6 2005 151 169
9. A.J. Wilson Chem. Soc. Rev. 38 2009 3289 3300
10. Our analogs incorporate an ethylene unit into the ring thus differentiating themselves from any cyclic tetrapeptide analogs. Synthetic efforts toward a cyclic tetrapeptide library has been disclosed recently. Lim, A.; Ong, A.; Chia, B. In Peptide Science 2010: Proceedings of the Fifth International Peptide Symposium; Fijii, N., Kiso, Y., Eds.; The Japanese Peptide Society: Osaka, 2011; p 216.
11. F. Berst, M. Ladlow, and A. Holmes Chem. Commun. 2002 508 509
12. P. Murray, M. Kranz, M. Ladlow, S. Taylor, F. Berst, A. Holmes, K. Keavey, A. Jaxa-Chamiec, P. Seale, P. Stead, R. Upton, S. Croft, W. Clegg, and M. Elsegood Bioorg. Med. Chem. Lett. 11 2001 773 776
13. Jaxa-Chamiec, A.; Kranz, M.; Murray, P. International Patent Application WO 00/47608
14. 4. There was no discussion about the optical purity of the cyclization product in the patent.
15. C.J. White, and A.K. Yudin Nat. Chem. 3 2011 509 524
16. M.M. Joullie, and K.M. Lassen Arkivoc 8 2010 189 250
17. M. Adamczyk, J. Fishpaugh, and K. Heuser Org. Prep. Proced. Int. 30 3 1998 339 348
18. Selective Boc-removal in the presence of t-butyl ester has been reported using p-toluenesulfonic acid or dry HCl. See J. Goodacre, R. Ponsford, and I. Stirling Tetrahedron Lett. 42 1975 3609 3612
19. F. Gibson, S. Bergmeier, and H. Rapoport J. Org. Chem. 59 1994 3216 3218
20. L. Di, C. Whitney-Pickett, H. Zhang, X. Zhang, D.F. Gebhard, Y. Lai, J.J. Federico III, R.E. Davidson, R. Smith, E.L. Revner, C. Lee, B. Feng, C. Rotter, M.V. Varma, S. Kempshall, K. Fenner, A.F. El-Kattan, T.E. Liston, and M.D. Troutman J. Pharm. Sci. 100 11 2011 4974 4985
21. T. Cierpicki, and J. Otlewski J. Biomol. NMR 21 2001 249 261
22. A. Alex, D. Millan, M. Perez, F. Wakenhut, and G. Whitlock Med. Chem. Commun. 2 2011 669 674