Structure-based design, synthesis and in vitro characterization of potent 17β-hydroxysteroid dehydrogenase type 1 inhibitors based on 2-substitutions of estrone and D-homo-estrone

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 23, 2009, Pages 6740-6744

  Möller, Gabriele ^a   Deluca, Dominga ^a   Gege, Christian ^b   Rosinus, Andrea ^a   Kowalik, Dorota ^a   Peters, Olaf ^b   Droescher, Peter ^b   Elger, Walter ^c   Adamski, Jerzy ^a   Hillisch, Alexander ^c  

^a INSTITUTE OF EPIDEMIOLOGY   (Germany)

^b BAYER PHARMA AG   (Germany)

^c EnTec GmbH   (Germany)

Author keywords

Cancer; Inhibitors; Molecular docking; Steroid metabolism; Structure based drug design

Indexed keywords

ANTINEOPLASTIC AGENT; ESTRADIOL; ESTRONE; TESTOSTERONE 17BETA DEHYDROGENASE TYPE 1 INHIBITOR; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CRYSTAL STRUCTURE; DRUG BINDING; DRUG DESIGN; DRUG INHIBITION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; IN VITRO STUDY; MOLECULAR DOCKING; STRUCTURE ACTIVITY RELATION; X RAY;

17-HYDROXYSTEROID DEHYDROGENASES; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; ENZYME INHIBITORS; ESTRONE; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 71749120228     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.09.113     Document Type: Article

References (64)

1. Hardy L.W., and Peet N.P. Drug Discovery Today 9 (2004) 117
2. Hopkins A.L., and Groom C.R. Nat. Rev. Drug Disc. 1 (2002) 727
3. Möller G., and Adamski J. Mol. Cell. Endocrinol. 301 (2009) 7
4. Vihko P., Härkönen P., Soronen P., Törn S., Herrala A., Kurkela R., Pulkka A., Oduwole O., and Isomaa V. Mol. Cell. Endocrinol. 215 (2004) 83
5. Luu-The V. J. Steroid Biochem. Mol. Biol. 76 (2001) 143
6. Persson B., Kallberg Y., Bray J.E., Bruford E., Dellaporta S.L., Favia A.D., Gonzalez Duarte R., Jörnvall H., Kavanagh K.L., Kedishvili N., Kisiela M., Maser E., Mindich R., Orchard S., Penning T.M., Thornton J.M., Adamski J., and Oppermann U. Chem. Biol. Interact. 178 (2009) 94
7. Jin Y., and Penning T.M. Annu. Rev. Pharmacol. Toxicol. 47 (2007) 263
8. Gunnarsson C., Hellqvist E., and Stål O. Br. J. Cancer 92 (2005) 547
9. Oduwole O.O., Li Y., Isomaa V.V., Mäntyniemi A., Pulkka A.E., Soini Y., and Vihko P.T. Cancer Res. 64 (2004) 7604
10. Nagasaki S., Suzuki T., Miki Y., Akahira J., Kitada K., Ishida T., Handa H., Ohuchi N., and Sasano H. Cancer Res. 69 (2009) 1392
11. Rasiah K.K., Gardiner-Garden M., Padilla E.J., Möller G., Kench J.G., Alles M.C., Eggleton S.A., Stricker P.D., Adamski J., Sutherland R.L., Henshall S.M., and Hayes V.M. Mol. Cell. Endocrinol. 301 (2009) 89
12. Einspanier A., Lieder K., Brüns A., Husen B., Thole H., and Simon C. Mol. Hum. Reprod. 12 (2006) 291
13. Šmuc T., Pucelj M.R., Sinkovec J., Husen B., Thole H., and Lanišnik Rižner T. Gynecol. Endocrinol. 23 (2007) 105
14. Day J.M., Tutill H.J., Purohit A., and Reed M.J. Endocr. Relat. Cancer 15 (2008) 665
15. Poirier D. Curr. Med. Chem. 10 (2003) 453
16. Poirier D. Anti-Cancer Agents Med. Chem. 19 (2009) 642
17. Lawrence H.R., Vicker N., Allan G.M., Smith A., Mahon M.F., Tutill H.J., Purohit A., Reed M.J., and Potter B.V.L. J. Med. Chem. 48 (2005) 2759
18. Tchedam Ngatcha B., Luu-The V., Labrie F., and Poirier D. J. Med. Chem. 48 (2005) 5257
19. Frotscher M., Ziegler E., Marchais-Oberwinkler S., Kruchten P., Neugebauer A., Fetzer L., Scherer C., Müller-Vieira U., Messinger J., Thole H., and Hartmann R.W. J. Med. Chem. 51 (2008) 2158
20. Breton R., Housset D., Mazza C., and FontecillaCamps J.C. Structure 4 (1996) 905
21. Morrissey C., and Watson R.W. Curr. Drug Targets 4 (2003) 231
22. Adlercreutz H. J. Steroid Biochem. Mol. Biol. 83 (2002) 113
23. Deluca D., Krazeisen A., Breitling R., Prehn C., Möller G., and Adamski J. J. Steroid Biochem. Mol. Biol. 93 (2005) 285
24. Brožič P., Lanišnik Rižner T.L., and Gobec S. Curr. Med. Chem. 15 (2008) 137
25. Tremblay M.R., Boivin R.P., Luu-The V., and Poirier D. J. Enzyme Inhib. Med. Chem. 20 (2005) 153
26. Poirier D., Chang H.J., Azzi A., Boivin R.P., and Lin S.X. Mol. Cell. Endocrinol. 248 (2006) 236
27. Allan G.M., Lawrence H.R., Cornet J., Bubert C., Fischer D.S., Vicker N., Smith A., Tutill H.J., Purohit A., Day J.M., Mahon M.F., Reed M.J., and Potter B.V.L. J. Med. Chem. 49 (2006) 1325
28. Vicker N., Lawrence H.R., Allan G.M., Bubert C., Smith A., Tutill H.J., Purohit A., Day J.M., Mahon M.F., Reed M.J., and Potter B.V.L. ChemMedChem 1 (2006) 464
29. Fischer D.S., Allan G.M., Bubert C., Vicker N., Smith A., Tutill H.J., Purohit A., Wood L., Packham G., Mahon M.F., Reed M.J., and Potter B.V.L. J. Med. Chem. 48 (2005) 5749
30. Schwarz S., Thieme I., Richter M., Undeutsch B., Henkel H., and Elger W. Steroids 61 (1996) 710
31. Poirier D., Ciobanu L.C., and Berube M. Bioorg. Med. Chem. Lett. 12 (2002) 2833
32. Deluca D., Möller G., Rosinus A., Elger W., Hillisch A., and Adamski J. Mol. Cell. Endocrinol. 248 (2006) 218
33. Qiu W., Campbell R.L., Gangloff A., Dupuis P., Boivin R.P., Tremblay M.R., Poirier D., and Lin S.X. FASEB J. 16 (2002) 1829
34. Berube M., and Poirier D. Org. Lett. 6 (2004) 3127
35. Brown W.M., Metzger L.E., Barlow J.P., Hunsaker L.A., Deck L.M., Royer R.E., and Vander Jagt D.L. Chem. Biol. Interact. 143-144 (2003) 481
36. Bey E., Marchais-Oberwinkler S., Kruchten P., Frotscher M., Werth R., Oster A., Algül O., Neugebauer A., and Hartmann R.W. Bioorg. Med. Chem. 16 (2008) 6423
37. Schuster D., Nashev L.G., Kirchmair J., Laggner C., Wolber G., Langer T., and Odermatt A. J. Med. Chem. 51 (2008) 4188
38. Allan G.M., Vicker N., Lawrence H.R., Tutill H.J., Day J.M., Huchet M., Ferrandis E., Reed M.J., Purohit A., and Potter B.V.L. Bioorg. Med. Chem. 16 (2008) 4438
39. Marchais-Oberwinkler S., Frotscher M., Ziegler E., Werth R., Kruchten P., Messinger J., Thole H., and Hartmann R.W. Mol. Cell. Endocrinol. 301 (2009) 205
40. Hillisch, A.; Regenhardt, W.; Gege, C.; Peters, O.; Bothe, U.; Adamski, J.; Möller, G.; Rosinus, A.; Elger, W.; Schneider, B. Patent WO06/003013, 2006.
41. Gege, C.; Regenhardt, W.; Peters, O.; Hillisch, A.; Adamski, J.; Möller, G.; Deluca, D.; Elger, W.; Schneider, B. Patent WO06/003012, 2006.
42. Leese M.P., Hejaz H.A., Mahon M.F., Newman S.P., Purohit A., Reed M.J., and Potter B.V.L. J. Med. Chem. 48 (2005) 5243
43. Bulman Page P.C., Hussain F., Maggs J.L., Morgan P., and Park B.K. Tetrahedron 46 (1990) 2059
44. Patton T.L. J. Org. Chem. 27 (1962) 910
45. Nambara T., Honma S., and Akiyama S. Chem. Pharm. Bull. 18 (1970) 474
46. Ito Y., Hirao T., and Seagusa T. J. Org. Chem. 43 (1978) 1011
47. Schwarz S., Thieme I., Kosemund D., Undeutsch B., Kummer M., Görls H., Römer W., Kaufmann G., Elger W., Hillisch A., and Schneider B. Pharmazie 56 (2001) 843
48. Paaren, H. E.; Duff, S. R. Patent US6448419B1, 2002.
49. Cushman M., He H.M., Katzenellenbogen J.A., Varma R.K., Hamel E., Lin C.M., Ram S., and Sachdeva Y.P. J. Med. Chem. 40 (1997) 2323
50. Stalford A.C., Maggs J.L., Gilchrist T.L., and Park B.K. Steroids 62 (1997) 750
51. Hübner M., and Noack I. J. Prakt. Chem. 314 (1972) 667
52. Hübner M., and Ponsold K. Z. Chem. 22 (1982) 186
53. Stavber S., Jereb M., and Zupan M. Synthesis (2002) 2609
54. Leenders F., Tesdorpf J.G., Markus M., Engel T., Seedorf U., and Adamski J. J. Biol. Chem. 271 (1996) 5438
55. Halgren T.A. J. Comp. Chem. 17 (1996) 490
56. Rarey M., Kramer B., Lengauer T., and Klebe G. J. Mol. Biol. 261 (1996) 470
57. Marchais-Oberwinkler S., Kruchten P., Frotscher M., Ziegler E., Neugebauer A., Bhoga U., Bey E., Müller-Vieira U., Messinger J., Thole H., and Hartmann R.W. J. Med. Chem. 51 (2008) 4685
58. Bey E., Marchais-Oberwinkler S., Werth R., Negri M., Al-Soud Y.A., Kruchten P., Oster A., Frotscher M., Birk B., and Hartmann R.W. J. Med. Chem. 51 (2008) 6725
59. Karkola S., Lilienkampf A., and Wähälä K. ChemMedChem 3 (2008) 461
60. Allan G.M., Bubert C., Vicker N., Smith A., Tutill H.J., Purohit A., Reed M.J., and Potter B.V.L. Mol. Cell. Endocrinol. 248 (2006) 204
61. Stomberg R., and Lundquist K. Z. Kristallogr. - New Cryst. Struct. 214 (1999) 403
62. Shi R., and Lin S.X. J. Biol. Chem. 279 (2004) 16778
63. Gangloff A., Shi R., Nahoum V., and Lin S.X. FASEB J. 17 (2003) 274
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