Fragment-based drug discovery of carbonic anhydrase II inhibitors by dynamic combinatorial chemistry utilizing alkene cross metathesis

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 10, 2006, Pages 3275-3284

  Poulsen, Sally Ann ^a   Bornaghi, Laurent F ^a  

^a GRIFFITH UNIVERSITY   (Australia)

Author keywords

Carbonic anhydrase; Cross metathesis; Dynamic combinatorial chemistry; Fragment based drug discovery; Sulfonamide

Indexed keywords

4 (ACYLOXY)BUT 2 ENYL 4 (AMINOSULFONYL)BENZOATE; 4 (BIPHENYLOXY)BUT 2 ENYL 4 (AMINOSULFONYL)BENZOATE; ACETAZOLAMIDE; ALKENE; BUT 2 EN 1,4 DIYL BIS[(AMINOSULFONYL)BENZOATE; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; SULFANILAMIDE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING ASSAY; CATALYSIS; CHEMICAL REACTION; COMBINATORIAL CHEMISTRY; DERIVATIZATION; DISSOCIATION CONSTANT; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG SCREENING; DRUG SYNTHESIS; NONHUMAN;

ALKENES; ANIMALS; CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; CATTLE; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DESIGN; ERYTHROCYTES; MOLECULAR STRUCTURE; PEPTIDE LIBRARY; SULFONAMIDES;

BOVINAE;

EID: 33645852593     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.12.054     Document Type: Article

References (32)

1. Lehn J.-M. Chem. Eur. J. 5 (1999) 2455
2. Rowan S.J., Cantrill S.J., Cousins G.R.L., Sanders J.K.M., and Stoddart J.F. Angew. Chem., Int. Ed. 41 (2002) 898
3. Ramström O., and Lehn J.-M. ChemBioChem 1 (2000) 41
4. Bunyapaiboonsri T., Ramström O., Lohmann S., Lehn J.-M., Peng L., and Goeldner M. ChemBioChem 2 (2001) 438
5. Huc I., and Lehn J.-M. Proc. Natl. Acad. Sci. U.S.A. 94 (1997) 2106
6. Nguyen R., and Huc I. Angew. Chem., Int. Ed. 40 (2001) 1774
7. Hochgürtel M., Kroth H., Piecha D., Hofmann M.W., Nicolau C., Krause S., Schaaf O., Sonnenmoser G., and Eliseev A.V. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 3382
8. Hochgürtel M., Biesinger R., Kroth H., Piecha D., Hofmann M.W., Krause S., Schaaf O., Nicolau C., and Eliseev A.V. J. Med. Chem. 46 (2003) 356
9. Congreve M.S., Davis D.J., Devine L., Granata C., O'Reilly M., Wyatt P.G., and Jhoti H. Angew. Chem., Int. Ed. 42 (2003) 4479
10. Bunyapaiboonsri T., Ramström H., Ramström O., Haiech J., and Lehn J.-M. J. Med. Chem. 46 (2003) 5803
11. Hong L., Williams P., Micklefield J., Gardiner J.M., and Stephens G. Tetrahedron 60 (2004) 753
12. Zameo S., Vauzeilles B., and Beau J.-M. Angew. Chem., Int. Ed. 44 (2005) 965
13. Pei, Z.; Larsson, R.; Aastrup, T.; Anderson, H.; Ramström, O. Abstracts of Papers, 230th ACS National Meeting, Washington, DC, United States, 2005.
14. Ramström O., Lohmann S., Bunyapaiboonsri T., and Lehn J.-M. Chemistry-A European Journal 10 (2004) 1711
15. Erlanson D.A., McDowell R.S., and O'Brien T. J. Med. Chem. 47 (2004) 3463
16. Nicolaou K.C., Hughes R., Cho S.Y., Winssinger N., Smethurst C., Labischinski H., and Endermann R. Angew. Chem., Int. Ed. 39 (2000) 3823
17. Supuran C.T., and Scozzafava A. Curr. Med. Chem.-Immunol. Endocrinol. Metab. Agents 1 (2001) 61
18. Pastorekova S., Parkkila S., Pastorek J., and Supuran C.T. J. Enzyme Inhib. Med. Chem. 19 (2004) 199
19. Scozzafava A., Owa T., Mastrolorenzo A., and Supuran C.T. Curr. Med. Chem. 10 (2003) 925
20. Pastorekova S., Casini A., Scozzafava A., Vullo D., Pastorek J., and Supuran C.T. Bioorg. Med. Chem. Lett. 14 (2004) 869
21. Supuran C.T. Expert Opin. Investig. Drugs 12 (2003) 283
22. Grubbs R.H., and Chang S. Tetrahedron 54 (1998) 4413
23. Grubbs R.H. Tetrahedron 60 (2004) 7117
24. Chatterjee A.K., Choi T.-L., Sanders D.P., and Grubbs R.H. J. Am. Chem. Soc. 125 (2003) 11360
25. Poulsen S.-A., Bornaghi L.F., and Healy P.C. Bioorg. Med. Chem. Lett. 15 (2005) 5429
26. Sigal G.B., and Whitesides G.M. Bioorg. Med. Chem. Lett. 6 (1996) 559
27. Chen R.F., and Kernohan J.C. J. Biol. Chem. 242 (1967) 5813
28. Poulsen S.-A., Davis R.D., and Keys T.G. Bioorg. Med. Chem. 14 (2006) 510
29. Poulsen S.-A., and Bornaghi L.F. Tetrahedron Lett. 46 (2005) 7389
30. Guo Q., Miyaji T., Hara R., Shen B., and Takahashi T. Tetrahedron 58 (2002) 7327
31. Crosignani S., Gonzales J., and Swinnen D. Org. Lett. 6 (2004) 4579
32. Cheng Y.-C., and Prusoff W.H. Biochem. Pharmacol. 22 (1973) 3099