Design and evaluation of fragment-like estrogen receptor tetrahydroisoquinoline ligands from a scaffold-detection approach

Journal of Medicinal Chemistry

Volumn 54, Issue 7, 2011, Pages 2005-2011

  Möcklinghoff, Sabine ^a,b   Van Otterlo, Willem A L ^c,d   Rose, Rolf ^b   Fuchs, Sascha ^a   Zimmermann, Tobias J ^c   Dominguez Seoane, Marta ^b   Waldmann, Herbert ^c   Ottmann, Christian ^b   Brunsveld, Luc ^a,b  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

^b CHEMICAL GENOMICS CENTRE OF THE MAX PLANCK SOCIETY   (Germany)

^c MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

^d UNIVERSITY OF THE WITWATERSRAND   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

ESTROGEN RECEPTOR; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; TETRAHYDROISOQUINOLINE;

ARTICLE; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

DRUG DESIGN; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; LIGANDS; MODELS, MOLECULAR; PROTEIN STRUCTURE, TERTIARY; SMALL MOLECULE LIBRARIES; SUBSTRATE SPECIFICITY; TETRAHYDROISOQUINOLINES;

EID: 79953795527     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1011116     Document Type: Article

References (39)

1. Hajduk, P. J.; Greer, J. A decade of fragment-based drug design: strategic advances and lessons learned Nature Rev. Drug Discovery 2007, 6, 211-219 (Pubitemid 46344625)
2. Siegel, M. G.; Vieth, M. Drugs in other drugs: a new look at drugs as fragments Drug Discovery Today 2007, 12, 71-79 (Pubitemid 46014488)
3. Congreve, M.; Chessari, G.; Tisi, D.; Woodhead, A. J. Recent developments in fragment-based drug discovery J. Med. Chem. 2008, 51, 3661-3680 (Pubitemid 351956496)
4. Koch, M. A.; Schuffenhauer, A.; Scheck, M.; Wetzel, S.; Casaulta, M.; Odermatt, A.; Ertl, P.; Waldmann, H. Charting biologically relevant chemical space: a structural classification of natural products (SCONP) Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 17272-17277 (Pubitemid 41740856)
5. Clark, A. M.; Labute, P. Detection and assignment of common scaffolds in project databases of lead molecules J. Med. Chem. 2009, 52, 469-483
6. Renner, S.; van Otterlo, W. A. L.; Dominguez Seoane, M.; Mocklinghoff, S.; Hofmann, B.; Wetzel, S.; Schuffenhauer, A.; Ertl, P.; Oprea, T. I.; Steinhilber, D.; Brunsveld, L.; Rauh, D.; Waldmann, H. Bioactivity-guided mapping and navigation of chemical space Nature Chem. Biol. 2009, 5, 585-592
7. Bon, R. S.; Waldmann, H. Bioactivity-Guided Navigation of Chemical Space Acc. Chem. Res. 2010, 43, 1103-1114
8. Sato, M.; Grese, T. A.; Dodge, J. A.; Bryant, H. U.; Turner, C. H. Emerging therapies for the prevention or treatment of postmenopausal osteoporosis J. Med. Chem. 1999, 42, 1-24 (Pubitemid 29056485)
9. Kuiper, G. G.; Carlsson, B.; Grandien, K.; Enmark, E.; Haggblad, J.; Nilsson, S.; Gustafsson, J. A. Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta Endocrinology 1997, 138, 863-870 (Pubitemid 27089735)
10. Green, S.; Walter, P.; Kumar, V.; Krust, A.; Bornert, J. M.; Argos, P.; Chambon, P. Human estrogen-receptor cDNA - sequence, expression and homology to v- erb-A Nature 1986, 320, 134-139 (Pubitemid 16105150)
11. Greene, G. L.; Gilna, P.; Waterfield, M.; Baker, A.; Hort, Y.; Shine, J. Sequence and expression of human estrogen-receptor complementary DNA Science 1986, 231, 1150-1154 (Pubitemid 16016313)
12. Kuiper, G. G. J. M.; Enmark, E.; Pelto-Huikko, M.; Nilsson, S.; Gustafsson, J. A. Cloning of a novel estrogen receptor expressed in rat prostate and ovary Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 5925-5930 (Pubitemid 26190778)
13. Mosselman, S.; Polman, J.; Dijkema, R. ER beta: identification and characterization of a novel human estrogen receptor FEBS Lett. 1996, 392, 49-53 (Pubitemid 26268330)
14. Zhang, W. H.; Andersson, S.; Cheng, G. J.; Simpson, E. R.; Warner, M.; Gustafsson, J. A. Update on estrogen signaling FEBS Lett. 2003, 546, 17-24 (Pubitemid 36789762)
15. Veeneman, G. H. Subtype-selective Estrogens. In Nuclear Receptors as Durg Targets; Ottow, E.; Weinmann, H., Eds.; Wiley-VCH: Weinheim, Germany, 2008; pp 65-126.
16. Nilsson, S.; Kuiper, G.; Gustafsson, J. A. ERbeta: a novel estrogen receptor offers the potential for new drug development Trends Endocrinol. Metab. 1998, 9, 387-395 (Pubitemid 28553623)
17. Miller, C. P. SERMs: evolutionary chemistry, revolutionary biology Curr. Pharm. Des. 2002, 8, 2089-2111 (Pubitemid 34982172)
18. Wallace, O. B.; Richardson, T. I.; Dodge, J. A. Estrogen receptor modulators: relationships of ligand structure, receptor affinity and functional activity Curr. Top. Med. Chem. 2003, 3, 1663-1680
19. Harris, H. A.; Albert, L. M.; Leathurby, Y.; Malamas, M. S.; Mewshaw, R. E.; Miller, C. P.; Kharode, Y. P.; Marzolf, J.; Komm, B. S.; Winneker, R. C.; Frail, D. E.; Henderson, R. A.; Zhu, Y.; Keith, J. C., Jr. Evaluation of an estrogen receptor-beta agonist in animal models of human disease Endocrinology 2003, 144, 4241-4249 (Pubitemid 37204818)
20. Artis, D. R. Scaffold-based discovery of indeglitazar, a PPAR pan-active anti-diabetic agent Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 262-267
21. Barlaam, B.; Dantzman, C. Preparation of isoquinolines and isoindolines as selective estrogen receptor- ligand. (AstraZeneca, PLC). Patent WO 2002/46164, 2002.
22. Chesworth, R.; Wessel, M. D.; Heyden, L.; Mangano, F. M.; Zawistoski, M.; Gegnas, L.; Galluzzo, D.; Lefker, B.; Cameron, K. O.; Tickner, J.; Lu, B. H.; Castleberry, T. A.; Petersen, D. N.; Brault, A.; Perry, P.; Ng, O.; Owen, T. A.; Pan, L.; Ke, H. Z.; Brown, T. A.; Thompson, D. D.; DaSilva-Jardine, P. Tetrahydroisoquinolines as subtype selective estrogen agonists/antagonists Bioorg. Med. Chem. Lett. 2004, 14, 2729-2733 (Pubitemid 38569728)
23. See for example: Paul, R.; Coppola, J. A.; Cohen, E. 1-Phenyl-2- phenylethyl-1,2,3,4-tetrahydroisoquinolines - new series of nonsteroidal female antifertility agents J. Med. Chem. 1972, 15, 720-726
24. Nagarajan, K.; Talwalker, P. K.; Kulkarni, C. L.; Shah, R. K.; Shenoy, S. J.; Prabhu, S. S. Antiimplantation agents 2. 1,2-Diaryl-1,2,3,4- tetrahydroisoquinolines Ind. J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1985, 24, 83-97
25. Renaud, J.; Bischoff, S. F.; Buhl, T.; Floersheim, P.; Fournier, B.; Geiser, M.; Halleux, C.; Kallen, J.; Keller, H.; Ramage, P. Selective estrogen receptor modulators with conformationally restricted side chains. Synthesis and structure-activity relationship of ERalpha-selective tetrahydroisoquinoline ligands J. Med. Chem. 2005, 48, 364-379
26. Lin, H. R.; Safo, M. K.; Abraham, D. J. Identification of a series of tetrahydroisoquinoline derivatives as potential therapeutic agents for breast cancer Bioorg. Med. Chem. Lett. 2007, 17, 2581-2589 (Pubitemid 46507769)
27. Hoye, T. R.; Renner, M. K.; Vos-DiNardo, T. J. Practical method for chemoselective formation of MTPA amide derivatives from amino alcohols and phenols J. Org. Chem. 1997, 62, 4168-4170
28. Möcklinghoff, S.; Rose, R.; Carraz, M.; Visser, A.; Ottmann, C.; Brunsveld, L. Synthesis and crystal structure of phosphorylated estrogen receptor ligand binding domain ChemBioChem 2010, 11, 2251-2254
29. Pike, A. C. W.; Brzozowski, A. M.; Hubbard, R. E.; Bonn, T.; Thorsell, A. G.; Engstrom, O.; Ljunggren, J.; Gustafsson, J. K.; Carlquist, M. Structure of the ligand-binding domain of oestrogen receptor beta in the presence of a partial agonist and a full antagonist EMBO J. 1999, 18, 4608-4618 (Pubitemid 29415516)
30. Brzozowski, A. M.; Pike, A. C. W.; Dauter, Z.; Hubbard, R. E.; Bonn, T.; Engstrom, O.; Ohman, L.; Greene, G. L.; Gustafsson, J. A.; Carlquist, M. Molecular basis of agonism and antagonism in the oestrogen receptor Nature 1997, 389, 753-758 (Pubitemid 27458965)
31. Norman, B. H.; Dodge, J. A.; Richardson, T. I.; Borromeo, P. S.; Lugar, C. W.; Jones, S. A.; Chen, K.; Wang, Y.; Durst, G. L.; Barr, R. J.; Montrose-Rafizadeh, C.; Osborne, H. E.; Amos, R. M.; Guo, S.; Boodhoo, A.; Krishnan, V. Benzopyrans are selective estrogen receptor beta agonists with novel activity in models of benign prostatic hyperplasia J. Med. Chem. 2006, 49, 6155-6157 (Pubitemid 44595191)
32. Richardson, T. I.; Dodge, J. A.; Wang, Y.; Durbin, J. D.; Krishnan, V.; Norman, B. H. Benzopyrans as selective estrogen receptor beta agonists (SERBAs). Part 5: Combined A- and C-ring structure-activity relationship studies Bioorg. Med. Chem. Lett. 2007, 17, 5563-5566 (Pubitemid 47391324)
33. Manas, E. S.; Unwalla, R. J.; Xu, Z. B.; Malamas, M. S.; Miller, C. P.; Harris, H. A.; Hsiao, C.; Akopian, T.; Hum, W. T.; Malakian, K.; Wolfrom, S.; Bapat, A.; Bhat, R. A.; Stahl, M. L.; Somers, W. S.; Alvarez, J. C. Structure-based design of estrogen receptor-beta selective ligands J. Am. Chem. Soc. 2004, 126, 15106-15119 (Pubitemid 39557270)
34. Pike, A. C. W.; Brzozowski, A. M.; Hubbard, R. E. A structural biologist's view of the oestrogen receptor J. Steroid Biochem. Mol. Biol. 2000, 74, 261-268 (Pubitemid 32140404)
35. Warnmark, A.; Treuter, E.; Gustafsson, J. A.; Hubbard, R. E.; Brzozowski, A. M.; Pike, A. C. W. Interaction of transcriptional intermediary factor 2 nuclear receptor box peptides with the coactivator binding site of estrogen receptor alpha J. Biol. Chem. 2002, 277, 21862-21868 (Pubitemid 34959959)
36. Shiau, A. K.; Barstad, D.; Loria, P. M.; Cheng, L.; Kushner, P. J.; Agard, D. A.; Greene, G. L. The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen Cell 1998, 95, 927-937 (Pubitemid 29019045)
37. Malamas, M. S.; Manas, E. S.; McDevitt, R. E.; Gunawan, I.; Xu, Z. B.; Collini, M. D.; Miller, C. P.; Dinh, T.; Henderson, R. A.; Keith, J. C.; Harris, H. A. Design and synthesis of aryl diphenolic azoles as potent and selective estrogen receptor-beta ligands J. Med. Chem. 2004, 47, 5021-5040 (Pubitemid 39314900)
38. Yang, C. J.; Edsall, R.; Harris, H. A.; Zhang, X. C.; Manas, E. S.; Mewshaw, R. E. ER beta ligands. Part 2: Synthesis and structure-activity relationships of a series of 4-hydroxy-biphenyl-carbaldehyde oxime derivatives Bioorg. Med. Chem. 2004, 12, 2553-2570 (Pubitemid 38542781)
39. Mewshaw, R. E.; Edsall, R. J.; Yang, C. J.; Manas, E. S.; Xu, Z. B.; Henderson, R. A.; Keith., J. C.; Harris, H. A. ER beta ligands. 3. Exploiting two binding orientations of the 2-phenylnaphthalene scaffold to achieve ER beta selectivity J. Med. Chem. 2005, 48, 3953-3979 (Pubitemid 40800606)