Synthesis and testing of trifluoromethyl-containing phosphonate-peptide conjugates as inhibitors of serine hydrolases

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 23, 2011, Pages 7216-7218

  Sokolova, Nadezhda V ^a   Nenajdenko, Valentine G ^a   Sokolov, Vladimir B ^b   Serebryakova, Olga G ^b   Makhaeva, Galina F ^b  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b INSTITUTE OF PHYSIOLOGICALLY ACTIVE COMPOUNDS   (Russian Federation)

Author keywords

Click chemistry; Inhibitors; Organophosphorous compounds; Peptides; Serine hydrolases

Indexed keywords

AZIDOPEPTIDE DERIVATIVE; ENZYME INHIBITOR; HYDROLASE; METHYLPHOSPHONIC ACID; PHOSPHINIC ACID DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; SERINE; SERINE HYDROLASE; UNCLASSIFIED DRUG;

ARTICLE; CLICK CHEMISTRY; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS;

CARBOXYLESTERASE; CATALYSIS; CHOLINESTERASE INHIBITORS; CLICK CHEMISTRY; ENZYME ACTIVATION; FLUORINE; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; PEPTIDES; PHOSPHONIC ACIDS; SERINE PROTEINASE INHIBITORS;

EID: 80255140427     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.09.030     Document Type: Article

References (28)

1. G.F. Makhaeva, A.Y. Aksinenko, V.B. Sokolov, O.G. Serebryakova, and R.J. Richardson Bioorg. Med. Chem. Lett. 19 2009 5528
2. G.F. Makhaeva, O.G. Serebryakova, N.P. Boltneva, T.G. Galenko, A.Y. Aksinenko, V.B. Sokolov, and I.V. Martynov Dokl. Biochem. Biophys. 423 2008 826
3. G.F. Makhaeva, V.I. Fetisov, V.B. Sokolov, V.L. Yankovskaya, T.V. Goreva, and I.V. Martynov Bioorg. Khim. 13 1987 33
4. M. Sieńczyk, and J. Oleksyszyn Curr. Med. Chem. 16 2009 1673
5. C.W. Tornøe, C. Cristensen, and M. Meldal J. Org. Chem. 67 2002 3057
6. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 114 2002 2708
7. M. Meldal, and C.W. Tornøe Chem. Rev. 108 2008 2952
8. H.C. Kolb, and K.B. Sharpless Drug Discovery Today 8 2003 1128
9. J.E. Moses, and A.D. Moorhouse Chem. Soc. Rev. 36 2007 1249
10. F. Amblard, J.H. Cho, and R.F. Schinazi Chem. Rev. 109 2009 4207
11. C. Droumaguet, C. Wang, and Q. Wang Chem. Soc. Rev. 39 2010 1233
12. A.H. El-Sagheer, and T. Brown Chem. Soc. Rev. 39 2010 1388
13. D.K. Dalvie, A.S. Kalgutkar, S.C. Khojasteh-Bakht, R.S. Obach, and J.P. O'Donnell Chem. Res. Toxicol. 15 2002 269
14. W.S. Horne, M.K. Yadav, C.D. Stout, and M.R. Ghadiri J. Am. Chem. Soc. 126 2004 15366
15. J.M. Holub, and K. Kirshenbaum Chem. Soc. Rev. 39 2010 1325
16. D.S. Pedersen, and A. Abell Eur. J. Org. Chem. 2011 2399
17. A.D. Moorhouse, and J.E. Moses ChemMedChem 3 2008 715
18. V. Aragão-Leoneti, V.L. Campo, A.S. Gomes, R.A. Field, and I. Carvalho Tetrahedron 66 2010 9475
19. C.O. Kappe, and E.V. Eycken Chem. Soc. Rev. 39 2010 1280
20. A. Domling, and I. Ugi Angew. Chem., Int. Ed. 39 2000 3168
21. A. Domling Chem. Rev. 106 2006 17
22. A.V. Gulevich, A.G. Zhdanko, R.V.A. Orru, and V.G. Nenajdenko Chem. Rev. 110 2010 5235
23. V.G. Nenajdenko, A.V. Gulevich, N.V. Sokolova, A.V. Mironov, and E.S. Balenkova Eur. J. Org. Chem. 2010 1445
24. N.V. Sokolova, G.V. Latyshev, N.V. Lukashev, and V.G. Nenajdenko Org. Biomol. Chem. 9 2011 4921
25. A. Saxena, A.M.G. Redman, X. Jiang, O. Lockridge, and B.P. Doctor Biochemistry 36 1997 14642
26. S. Bencharit, C.C. Edwards, C.L. Morton, E.L. Howard-Williams, P. Kuhn, P.M. Potter, and M.R. Redinbo J. Mol. Biol. 363 2006 201
27. S. Bencharit, C.L. Morton, J.L. Hyatt, P. Kuhn, M.K. Danks, P.M. Potter, and M.R. Redinbo Chem. Biol. 10 2003 341
28. M.J. Hatfield, and P.M. Potter Expert Opin. Ther. Pat. 21 2011 1159