Improved synthesis of EM-1745, preparation of its C17-ketone analogue and comparison of their inhibitory potency on 17β-hydroxysteroid dehydrogenase type 1

References

• BE Henderson, R Ross, L Bernstein. Estrogens as a cause of human cancer: The Richard and Hinda Rosenthal foundation award lecture. Cancer Res 1988;48:246–253.
   PubMed Web of Science ®Google Scholar
• ME Lippman, RB Dickson, S Bates, C Knabbe, K Huff, S Swain, M McManaway, D Bronzert, A Kasid, EP Gelmann. Autocrine and paracrine growth regulation of human breast cancer. Breast Cancer Res Treat 1986;7:59–70.
   PubMed Web of Science ®Google Scholar
• HJ Smith, PJ Nicholls, C Simons, R Le Lain. Inhibitors of steroidogenesis as agents for the treatment of hormone-dependent cancers. Exp Opin Ther Patents 2001;11:789–824.
   Web of Science ®Google Scholar
• JI Macgregor, VC Jordan. Basic guide to the mechanisms of antiestrogen action. Pharmacol Rev 1998;50:151–196.
   PubMed Web of Science ®Google Scholar
• JR Pasqualini, GS Chetrite. Recent insight on the control of enzymes involved in estrogen formation and transformation in human breast cancer. J Steroid Biochem Mol Biol 2005;93:221–236.
   PubMed Web of Science ®Google Scholar
• AH Payne, DB Hales. Overview of steroidogenic enzymes in the pathway from cholesterol to active steroid hormones. Endocr Rev 2006;25:947–970.
   Web of Science ®Google Scholar
• D Poirier, R Maltais. Solid-phase organic synthesis (SPOS) of modulators of estrogenic and androgenic action. Mini-Rev Med Chem 2006;6:37–52.
   PubMed Web of Science ®Google Scholar
• RW Brueggemeier, JC Hackett, ES Diaz-Cruz. Aromatase inhibitors in the treatment of breast cancer. Endocr Rev 2005;23:331–345.
   Web of Science ®Google Scholar
• RJ Santen. Inhibition of aromatase: Insights from recent studies. Steroids 2003;68:559–567.
   PubMed Web of Science ®Google Scholar
• IE Smith, M Dowsett. Aromatase inhibitors in breast cancer. N Engl J Med 2003;348:2431–2442.
   PubMed Web of Science ®Google Scholar
• MJ Reed, A Purohit, LWL Woo, SP Newman, BVL Potter. Steroid sulfatase: Molecular biology, regulation, and inhibition. Endocr Rev 2005;26:171–202.
   PubMed Web of Science ®Google Scholar
• P Nussbaumer, A Billich. Steroid sulfatase inhibitors. Med Res Rev 2004;24:529–576.
   PubMed Web of Science ®Google Scholar
• S Ahmed, CP Owen, K James, L Sampson, CK Patel. Review of estrone sulfatase and its inhibitors–An important new target against hormone dependent breast cancer. Curr Med Chem 2002;9:263–273.
   PubMed Web of Science ®Google Scholar
• D Poirier, LC Ciobanu, R Maltais. Steroid sulfatase inhibitors. Exp Opin Ther Patents 1999;9:1083–1099.
   Web of Science ®Google Scholar
• LJ Langer, LL Engel. Human placental estradiol-17β dehydrogenase. I. Concentration, characterization and assay. J Biol Chem 1958;233:583–588.
   PubMed Web of Science ®Google Scholar
• KJ Ryan, LL Engel. The interconversion of estrone and estradiol by human tissue slices. Endocrinology 1953;52:287–291.
   PubMed Web of Science ®Google Scholar
• G Moller, J Adamski. Multifunctionality of human 17β-hydroxysteroid dehydrogenases. Mol Cell Endocrinol 2006;248:47–55.
   PubMed Web of Science ®Google Scholar
• P Lukacik, KL Kavanagh, U Oppermann. Structure and function of human 17β-hydroxysteroid dehydrogenases. Mol Cell Endocrinol 2006;248:61–71.
   PubMed Web of Science ®Google Scholar
• V Luu-The. Analysis and characteristics of multiple types of human 17β-hydroxysteroid dehydrogenase. J Steroid Biochem Mol Biol 2001;76:143–151.
   PubMed Web of Science ®Google Scholar
• TM Penning. Molecular endocrinology of hydroxysteroid dehydrogenases. Endocr Rev 1997;18:281–305.
   PubMed Web of Science ®Google Scholar
• C Martel, E Rhéaume, M Takahashi, C Trudel, J Couet, V Luu-The, J Simard, F Labrie. J Distribution of 17β-hydroxysteroid dehydrogenase gene expression and activity in rat and human tissues. J Steroid Biochem Mol Biol 1992;41:597–603.
   PubMed Web of Science ®Google Scholar
• V Speirs, AR Green, DS Walton, SL Atkins. Short-term primary culture of epithelial cells derived from breast tumours. Br J Cancer 1998;78:1421–1429.
   PubMed Web of Science ®Google Scholar
• N Ariga, T Moriya, T Suzuki, M Kimura, N Ohuchi, S Satomi, H Sasano. 17 beta-Hydroxysteroid dehydrogenase type 1 and type 2 in ductal carcinoma in situ and intraductal proliferative lesions of the human breast. Anticancer Res 2000;20:1101–1108.
   PubMed Web of Science ®Google Scholar
• C Gunnarsson, BM Olson, O Stal. Abnormal expression of 17β-hydroxysteroid dehydrogenases in breast cancer predicts late recurrence. Cancer Res 2001;61:8448–8451.
   PubMed Web of Science ®Google Scholar
• OO Oduwole, Y Li, VV Isomaa, A Mantyniemi, AE Pulkka, Y Soini, PT Vihko. 17β-Hydroxysteroid dehydrogenase type 1 is an independent prognostic marker in breast cancer. Cancer Res 2004;64:7604–7609.
   PubMed Web of Science ®Google Scholar
• V Speirs, DS Walton, MC Hall, SL Atkins. In vivo and in vitro expression of steroid-converting enzymes in human breast tumours: Associations with interleukin-6. Br J Cancer 1999;81:690–695.
   PubMed Web of Science ®Google Scholar
• M Miettinen, M Mustonen, M Poutanen, V Isomaa, M Wickman, G Soderquist, R Vihko, P Vihko. 17β-Hydroxysteroid dehydrogenases in normal human mammary epithelial cells and breast tissue. Breast Cancer Res Treat 1999;57:175–182.
   PubMed Web of Science ®Google Scholar
• TM Penning. 17β-Hydroxysteroid dehydrogenase: Inhibitors and inhibitor design. Endocr Relat Cancer 1996;3:41–56.
   Web of Science ®Google Scholar
• D Poirier. Inhibitors of 17β-hydroxysteroid dehydrogenases. Curr Med Chem 2003;10:1241–1253.
   Web of Science ®Google Scholar
• S Gobec, P Brozic, TL Rizner. Inhibitors of 17β-hydroxysteroid dehydrogenase type 1. Curr Med Chem 2008;15:137–150.
   PubMed Web of Science ®Google Scholar
• J Day, H Tutill, A Purohit, M Reed. Design and validation of specific inhibitors of 17{β}-hydroxysteroid dehydrogenases for therapeutic application in breast and prostate cancer, and in endometriosis Endocr Relat Cancer 2008, doi:10.1677/ERC-08-0042 (9 June 2008).
   Google Scholar
• D Fournier, D Poirier, M Mazumdar, SX Lin. Design and synthesis of bisubstrate inhibitors of type 1 17β-hydroxysteroid dehydrogenase: Overview and perspectives Eur J Med Chem 2008., doi:10.1016/j.ejmech.2008.01.044 (14 February 2008).
   Google Scholar
• E Bey, S Marchais-Oberwinkler, P Kruchten, M Frotscher, R Werth, A Oster, O Algul, A Neugebauer, RW Hartmann. Design, synthesis and biological evaluation of bis(hydroxyphenyl) azoles as potent and selective non-steroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) for the treatment of estrogen-dependent diseases. Bioorg Med Chem 2008;16:6423–6435.
   PubMed Web of Science ®Google Scholar
• M Frotscher, E Ziegler, S Marchais-Oberwinkler, P Kruchten, A Neugebauer, L Fetzer, C Scherer, U Muller-Vieira, J Messinger, H Thole, RW Hartmann. Design, synthesis, and biological evaluation of (hydroxyphenyl)naphthalene and -quinoline derivatives: Potent and selective nonsteroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) for the treatment of estrogen-dependent diseases. J Med Chem 2008;51:2158–2169.
   PubMed Web of Science ®Google Scholar
• S Karkola, A Lilienkampf, K Wahala. A 3D QSAR model of 17β-HSD1 inhibitors based on a thieno[2,3-d] pyrimidin-4(3H)-one core applying molecular dynamics simulations and ligand-protein docking. Chem Med Chem 2008;3:461–472.
   Web of Science ®Google Scholar
• GM Allan, N Vicker, HR Lawrence, HJ Tutill, JM Day, M Huchet, E Ferrandis, MJ Reed, A Purohit, BVL Potter. Novel inhibitors of 17β-hydroxysteroid dehydrogenase type 1: Templates for design. Bioorg Med Chem 2008;16:4438–4456.
   PubMed Web of Science ®Google Scholar
• D Schuster, LG Nashev, J Kirchmair, C Laggner, G Wolber, T Langer, A Odermatt. Discovery of nonsteroidal 17β-hydroxysteroid dehydrogenase 1 inhibitors by pharmacophore-based screening of virtual compound libraries J Med Chem 2008, (in press).
   Google Scholar
• A Azzi, PH Rhese, DW Zhu, RL Campbell, F Labrie, SX Lin. Crystal structure of human estrogenic 17β-hydroxysteroid dehydrogenase complexed with 17β-estradiol. Nat Struct Biol 1996;3:665–668.
   PubMedGoogle Scholar
• D Ghosh, VZ Pletnev, DW Zhu, Z Wawrzak, WL Duax, W Pangborn, F Labrie, SX Lin. 1995. Structure of human estrogenic 17β-hydroxysteroid dehydrogenase at 2.20A resolution. 3:503–513.
   Google Scholar
• SX Lin, DW Zhu, A Azzi, RL Campbell, R Breton, F Labrie, D Ghosh, V Pletnev, WL Duax, W Pangborn. Studies on the three-dimensional structure of estrogenic 17β-hydroxysteroid dehydrogenase. J Endocrinol 1996;150:S13–S20.
   PubMed Web of Science ®Google Scholar
• D Poirier, RP Boivin, MR Tremblay, M Bérubé, W Qiu, SX Lin. Estradiol-adenosine hybrid compounds designed to inhibit type 1 17β-hydroxysteroid dehydrogenase. J Med Chem 2005;48:8134–8147.
   PubMed Web of Science ®Google Scholar
• W Qiu, RL Campbell, A Gangloff, P Dupuis, RP Boivin, MR Tremblay, D Poirier, SX Lin. A concerted, rational design of type 1 17β-hydroxysteroid dehydrogenase inhibitors: Estradiol-adenosine hybrids with high affinity. FASEB J 2002;16:1829–1831.
   PubMed Web of Science ®Google Scholar
• M Bérubé, D Poirier. Synthesis of simplified hybrid inhibitors of type 1 17β-hydroxysteroid dehydrogenase via cross-metathesis and Sonogashira coupling reactions. Org Lett 2004;6:3127–3130.
   PubMed Web of Science ®Google Scholar
• JZ Jin, SX Lin. Human estrogenic 17β-hydroxysteroid dehydrogenase: Predominance of estrone reduction and its induction by NADPH. Biochem Biophys Res Commun 1999;259:489–493.
   PubMed Web of Science ®Google Scholar
• M Berube, Y Laplante, D Poirier. Design, synthesis and in vitro evaluation of 4-androstene-3,17-dione/adenosine hybrid compounds as bisubstrate inhibitors of type 3 17β-hydroxysteroid dehydrogenase. Med Chem 2006;2:329–347.
   PubMedGoogle Scholar
• P Dionne, BT Nagatcha, D Poirier. D-ring allyl derivatives of 17β- and 17α-estradiols: Chemical synthesis and 13C NMR data. Steroids 1997;62:674–681.
   PubMed Web of Science ®Google Scholar
• D Poirier, RP Boivin, M Berube, SX Lin. Synthesis of a first estradiol-adenosine hybrid compound. Synth Commun 2003;33:3183–3191.
   Web of Science ®Google Scholar
• MR Tremblay, D Poirier. Solid-phase synthesis of phenolic steroids: From optimization studies to a convenient procedure for combinatorial synthesis of biologically relevant estradiol derivatives. J Comb Chem 2000;2:48–65.
   PubMedGoogle Scholar
• MR Tremblay, SX Lin, D Poirier. Chemical synthesis of 16β-propylaminoacyl derivatives of estradiol and their inhibitory potency on type 1 17β-hydroxysteroid dehydrogenase and binding affinity on steroid receptors. Steroids 2001;66:821–831.
   PubMed Web of Science ®Google Scholar
• SJ Connon, S Blechert. Recent developments in olefin cross-metathesis. Angew Chem Int Ed 2003;42:1900–1923.
   PubMed Web of Science ®Google Scholar
• C Cadot, Y Laplante, F Kamal, V Luu-The, D Poirier. C6-(N,N-butyl-methyl-heptanamide) derivatives of estrone and estradiol as inhibitors of type 1 17β-hydroxysteroid dehydrogenase: Chemical synthesis and biological evaluation. Bioorg Med Chem 2007;15:714–726.
   PubMed Web of Science ®Google Scholar
• D Poirier, P Dionne, S Auger. A 6β-(thiaheptanamide) derivative of estradiol as inhibitor of 17β-hydroxysteroid dehydrogenase type 1. J Steroid Biochem Mol Biol 1998;64:83–90.
   PubMed Web of Science ®Google Scholar
• Y Laplante, C Cadot, MA Fournier, D Poirier. Estradiol and estrone C-16 derivatives as inhibitors of type 1 17β-hydroxystreroid dehydrogenase: Blocking of ER+ breast cancer cell proliferation induced by estrone. Bioorg Med Chem 2008;16:1849–1860.
   PubMed Web of Science ®Google Scholar
• KY Sam, RP Boivin, MR Tremblay, S Auger, D Poirier. C16 and C17 derivatives of estradiol as inhibitors of 17β-hydroxysteroid dehydrogenase type 1: Chemical synthesis and structure-activity relationships. Drug Design Discov 1998;15:157–180.
   PubMedGoogle Scholar