Estrone formate: A novel type of irreversible inhibitor of human steroid sulfatase

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 19, 2004, Pages 4999-5002

  Schreiner, Erwin P ^a   Billich, Andreas ^a  

^a Novartis Institutes Biomed Res GDC   (Austria)

Author keywords

Estrone formate; Inactivator; Steroid sulfatase

Indexed keywords

ACETIC ACID; BENZOXAZOLE DERIVATIVE; CARBAMIC ACID; CYANIC ACID; ENZYME INHIBITOR; ESTRONE DERIVATIVE; ESTRONE FORMATE; FORMIC ACID; STEROID; STERYL SULFATASE; THIOCARBAMIC ACID; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CHO CELL; CONCENTRATION RESPONSE; DRUG ACTIVITY; DRUG POTENCY; ENZYME ASSAY; ENZYME INHIBITION; IC 50; NONHUMAN;

BINDING SITES; ENZYME INHIBITORS; ESTRONE; FORMATES; HUMANS; STERYL-SULFATASE;

EID: 4444249442     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.07.013     Document Type: Article

References (30)

1. For reviews see: J.R. Pasqualini, C. Gelly, B.L. Nguyen, and C. Vella J. Steroid Biochem. 34 1989 155
2. M.J. Reed, and A. Purohit Rev. Endocrine Related Cancer 45 1993 51
3. D. Poirier, L.C. Ciobanu, and R. Maltais Exp. Opin. Ther. Patents 9 1999 1083
4. P. Nussbaumer, and A. Billich Exp. Opin. Ther. Patents 13 2003 605
5. N.M. Howarth, G. Cooper, A. Purohit, L. Duncan, M.J. Reed, and B.V.L. Potter Bioorg. Med. Chem. Lett. 3 1993 313
6. P.-K. Li, R. Pillai, and L. Dibbelt Steroids 60 1995 299
7. N.M. Howarth, A. Purohit, M.J. Reed, and B.V.L. Potter J. Med. Chem. 37 1994 219
8. A. Purohit, G.J. Williams, N.M. Howarth, B.L.V. Potter, and M.J. Reed Biochemistry 34 1995 11508
9. P. Nussbaumer, P. Lehr, and A. Billich J. Med. Chem. 73 2002 4310
10. Billich, A.; Schreiner, E. P.; Wolff-Winiski, B. 2001, WO 0136398 A1
11. 3) δ 220.5, 154.5, 137.5, 136.0, 128.7, 127.6, 126.2, 121.6, 118.8, 50.3, 47.9, 45.2, 44.0, 37.9, 35.8, 31.5, 29.3, 26.3, 25.7, 21.5, 13.7
12. D. Onken, K. Kutz, and D. Martin Zeitschr. f. Chem. 11 1971 65
13. D. Onken, D. Martin, and S. Rackow Zeitschr. f. Chem. 9 1969 228
14. E. Grigat, and R. Puetter Chem. Ber. 98 1965 1186
15. 3) δ 220.8, 192.1, 151.3, 137.9, 126.2, 122.2, 119.5, 50.4, 47.9, 44.2, 37.9, 35.8, 31.5, 29.4, 26.3, 25.7, 21.6, 13.8
16. R.W.H. Edwards J. Chromatogr. 12 1963 212
17. 3) δ 220.3, 167.0, 147.8, 138.1, 138.0, 126.3, 121.2, 118.5, 50.4, 47.7, 44.0, 42.5, 37.8, 35.7, 31.5, 29.3, 26.3, 21.5, 13.7
18. A. Billich, P. Nussbaumer, and P. Lehr J. Steroid Biochem. Mol. Biol. 73 2000 225
19. S. Ahmed, C.P. Owen, K. James, C.K. Patel, and L. Sampson J. Steroid Biochem. Mol. Biol. 80 2002 429
20. L.C. Ciobanu, R.P. Boivin, V. Luu-The, and D. Poirier J. Enzyme Inhib. Med. Chem. 18 2003 15
21. 4 solution and brine. The solvent was evaporated and the residue was purified by chromatography over silica gel with EtOAc/c-hexane (1/2) providing 240 mg (76%) of 17 as a white crystalline solid
22. J.R. Pliego, and J.M. Riveros Chem. Eur. J. 7 2001 169
23. S. Ahmed, K. James, C.P. Owen, K.C. Patel, and L. Sampson J. Steroid Biochem. Mol. Biol. 80 2002 429
24. L.W.L. Woo, M. Lightowler, A. Purohit, M.J. Reed, and B.L.V. Potter J. Steroid Biochem. Mol. Biol. 57 1996 79
25. J.C. Powers, R. Seidner, T.G. Parsons, and H.J. Berwin J. Org. Chem. 31 1966 2623
26. Lithiated amines react with carbon monoxide even in the absence of a transition metal to form formamides, see: N.S. Nudelman, and D. Perez J. Org. Chem. 48 1983 133
27. H.L. Yale J. Org. Chem. 36 1971 3238
28. D.G. Laplante, S. Manku, and J. Nagendran J. Org. Chem. 64 1999 698
29. J. Martinez, and J. Laur Synthesis 1982 979
30. N.M. Howarth, T. Purohit, J.J. Robinson, N. Vicker, M.J. Reed, and B.L.V. Potter Biochemistry 41 2002 14801