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Volumn 4, Issue 12, 2009, Pages 2098-2102

Synthesis and pharmacological evaluation of dimeric follicle-stimulating hormone receptor antagonists

(6) Bonger, Kimberly M a Hoogendoorn, Sascha a Van Koppen, Chris J b Timmers, Cornelis M b Overkleeft, Herman S a Van Der Marel, Gijsbert A a

a LEIDEN UNIVERSITY (Netherlands)

b MERCK RESEARCH LABORATORIES (United States)

Author keywords

Medicinal chemistry; Membrane proteins; Receptors; Signal transduction; Structure activity relationships

Indexed keywords

ETHYLENE GLYCOL; FOLLITROPIN RECEPTOR BINDING INHIBITOR;

ARTICLE; DIMERIZATION; DRUG CONFORMATION; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ENANTIOMER; FRIEDEL CRAFTS REACTION; HUMAN; IC 50; PHARMACOPHORE; PRIORITY JOURNAL;

ANIMALS; CHO CELLS; CRICETINAE; CRICETULUS; DIMERIZATION; LIGANDS; MOLECULAR STRUCTURE; RECEPTORS, FSH; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 73449123404 PISSN: 18607179 EISSN: 18607187 Source Type: Journal
DOI: 10.1002/cmdc.200900344 Document Type: Article

Times cited : (18)

References (31)

1
- 24944502148
- S. Costagliola, E. Urizar, F. Mendive, G. Vassart, Reproduction 2005, 130, 275-281.
- (2005) Reproduction , vol.130 , pp. 275-281
- Costagliola, S.¹ Urizar, E.² Mendive, F.³ Vassart, G.⁴

2
- 1542316313
- G. Vassart, L. Pardo, S. Costagliola, Trends Biochem. Sci. 2004, 29, 119-126.
- (2004) Trends Biochem. Sci , vol.29 , pp. 119-126
- Vassart, G.¹ Pardo, L.² Costagliola, S.³

3
- 0036217072
- M. Ascoli, F. Fanelli, D. L. Segaloff, Endocr. Rev. 2002, 23, 141-174.
- (2002) Endocr. Rev , vol.23 , pp. 141-174
- Ascoli, M.¹ Fanelli, F.² Segaloff, D.L.³

4
- 0031457992
- M. Simoni, J. Gromoll, E. Nieschlag, Endocr. Rev. 1997, 18, 739-773.
- (1997) Endocr. Rev , vol.18 , pp. 739-773
- Simoni, M.¹ Gromoll, J.² Nieschlag, E.³

5
- 0037020293
- N. C. van Straten, G. G. Schoonus-Gerritsma, R. G. van Someren, J. Draaijer, A. E. Adang, C. M. Timmers, R. G. Hanssen, C. A. van Boeckel, ChemBioChem 2002, 3, 1023-1026.
- (2002) ChemBioChem , vol.3 , pp. 1023-1026
- van Straten, N.C.¹ Schoonus-Gerritsma, G.G.² van Someren, R.G.³ Draaijer, J.⁴ Adang, A.E.⁵ Timmers, C.M.⁶ Hanssen, R.G.⁷ van Boeckel, C.A.⁸

6
- 54249130252
- C. J. van Koppen, G. J. Zaman, C. M. Timmers, J. Kelder, S. Mosselman, R. van de Lagemaat, M. J. Smit, R. G. Hanssen, Naunyn-Schmiedeberg's Arch. Pharmacol. 2008, 378, 503-514.
- (2008) Naunyn-Schmiedeberg's Arch. Pharmacol , vol.378 , pp. 503-514
- van Koppen, C.J.¹ Zaman, G.J.² Timmers, C.M.³ Kelder, J.⁴ Mosselman, S.⁵ van de Lagemaat, R.⁶ Smit, M.J.⁷ Hanssen, R.G.⁸

7
- 73449132090
- R. G. Hanssen, C. M. Timmers, WO03020726, 2003.
- R. G. Hanssen, C. M. Timmers, WO03020726, 2003.

8
- 20144367831
- N. C. van Straten, T. H. van Berkel, D. R. Demont, W. J. Karstens, R. Merkx, J. Med. Chem. 2005, 48, 1697-1700.
- (2005) J. Med. Chem , vol.48 , pp. 1697-1700
- van Straten, N.C.¹ van Berkel, T.H.² Demont, D.R.³ Karstens, W.J.⁴ Merkx, R.⁵

9
- 12144286406
- T. Guo, A. E. Adang, R. E. Dolle, G. Dong, D. Fitzpatrick, P. Geng, K. K. Ho, S. G. Kultgen, R. Liu, E. McDonald, B. F. McGuinness, K. W. Saionz, K. J. Valenzano, N. C. van Straten, D. Xie, M. L. Webb, Bioorg. Med. Chem. Lett. 2004, 14, 1713 -1716.
- (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 1713-1716
- Guo, T.¹ Adang, A.E.² Dolle, R.E.³ Dong, G.⁴ Fitzpatrick, D.⁵ Geng, P.⁶ Ho, K.K.⁷ Kultgen, S.G.⁸ Liu, R.⁹ McDonald, E.¹⁰ McGuinness, B.F.¹¹ Saionz, K.W.¹² Valenzano, K.J.¹³ van Straten, N.C.¹⁴ Xie, D.¹⁵ Webb, M.L.¹⁶

10
- 12144290509
- T. Guo, A. E. Adang, G. Dong, D. Fitzpatrick, P. Geng, K. K. Ho, C. H. Jibilian, S. G. Kultgen, R. Liu, E. McDonald, K. W. Saionz, K. J. Valenzano, N. C. van Straten, D. Xie, M. L. Webb, Bioorg. Med. Chem. Lett. 2004, 14, 1717 -1720.
- (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 1717-1720
- Guo, T.¹ Adang, A.E.² Dong, G.³ Fitzpatrick, D.⁴ Geng, P.⁵ Ho, K.K.⁶ Jibilian, C.H.⁷ Kultgen, S.G.⁸ Liu, R.⁹ McDonald, E.¹⁰ Saionz, K.W.¹¹ Valenzano, K.J.¹² van Straten, N.C.¹³ Xie, D.¹⁴ Webb, M.L.¹⁵

11
- 11144356160
- D. Maclean, F. Holden, A. M. Davis, R. A. Scheuerman, S. Yanofsky, C. P. Holmes, W. L. Fitch, K. Tsutsui, R. W. Barrett, M. A. Gallop, J. Comb. Chem. 2004, 6, 196-206.
- (2004) J. Comb. Chem , vol.6 , pp. 196-206
- Maclean, D.¹ Holden, F.² Davis, A.M.³ Scheuerman, R.A.⁴ Yanofsky, S.⁵ Holmes, C.P.⁶ Fitch, W.L.⁷ Tsutsui, K.⁸ Barrett, R.W.⁹ Gallop, M.A.¹⁰

12
- 0036772776
- B. J. Arey, D. C. Deecher, E. S. Shen, P. E. Stevis, E. H. Meade, Jr., J. Wrobel, D. E. Frail, F. J. Lopez, Endocrinology 2002, 143, 3822-3829.
- (2002) Endocrinology , vol.143 , pp. 3822-3829
- Arey, B.J.¹ Deecher, D.C.² Shen, E.S.³ Stevis, P.E.⁴ Meade Jr., E.H.⁵ Wrobel, J.⁶ Frail, D.E.⁷ Lopez, F.J.⁸

13
- 61449108160
- R. van de Lagemaat, C. M. Timmers, J. Kelder, C. van Koppen, S. Mosselman, R. G. Hanssen, Hum. Reprod. 2009, 24, 640- 648.
- (2009) Hum. Reprod , vol.24 , pp. 640-648
- van de Lagemaat, R.¹ Timmers, C.M.² Kelder, J.³ van Koppen, C.⁴ Mosselman, S.⁵ Hanssen, R.G.⁶

14
- 67749127694
- K. M. Bonger, R. J. B. H. N. van den Berg, A. D. Knijnenburg, L. H. Heitman, C. J. van Koppen, C. M. Timmers, H. S. Overkleeft, G. A. van der Marel, ChemMedChem 2009, 4, 1189-1195.
- (2009) ChemMedChem , vol.4 , pp. 1189-1195
- Bonger, K.M.¹ van den Berg, R.J.B.H.N.² Knijnenburg, A.D.³ Heitman, L.H.⁴ van Koppen, C.J.⁵ Timmers, C.M.⁶ Overkleeft, H.S.⁷ van der Marel, G.A.⁸

15
- 33751225377
- Y. Lei, G. M. Hagen, S. M. Smith, J. Liu, G. Barisas, D. A. Roess, Mol. Cell. Endocrinol. 2007, 260-262, 65-72.
- (2007) Mol. Cell. Endocrinol , vol.260-262 , pp. 65-72
- Lei, Y.¹ Hagen, G.M.² Smith, S.M.³ Liu, J.⁴ Barisas, G.⁵ Roess, D.A.⁶

16
- 21244460359
- E. Urizar, L. Montanelli, T. Loy, M. Bonomi, S. Swillens, C. Gales, M. Bouvier, G. Smits, G. Vassart, S. Costagliola, EMBO J. 2005, 24, 1954-1964.
- (2005) EMBO J , vol.24 , pp. 1954-1964
- Urizar, E.¹ Montanelli, L.² Loy, T.³ Bonomi, M.⁴ Swillens, S.⁵ Gales, C.⁶ Bouvier, M.⁷ Smits, G.⁸ Vassart, G.⁹ Costagliola, S.¹⁰

17
- 34249792937
- R. M. Thomas, C. A. Nechamen, J. E. Mazurkiewicz, M. Muda, S. Palmer, J. A. Dias, Endocrinology 2007, 148, 1987-1995.
- (2007) Endocrinology , vol.148 , pp. 1987-1995
- Thomas, R.M.¹ Nechamen, C.A.² Mazurkiewicz, J.E.³ Muda, M.⁴ Palmer, S.⁵ Dias, J.A.⁶

18
- 1242272013
- Y. X. Tao, N. B. Johnson, D. L. Segaloff, J. Biol. Chem. 2003, 279, 5904-5914.
- (2003) J. Biol. Chem , vol.279 , pp. 5904-5914
- Tao, Y.X.¹ Johnson, N.B.² Segaloff, D.L.³

19
- 0344739567
- D. A. Roess, S. M. Smith, Biol. Reprod. 2003, 69, 1765 -1770.
- (2003) Biol. Reprod , vol.69 , pp. 1765-1770
- Roess, D.A.¹ Smith, S.M.²

20
- 33751217461
- M. Jeoung, C. Lee, I. Ji, T. H. Ji, Mol. Cell. Endocrinol. 2007, 260-262, 137- 143.
- (2007) Mol. Cell. Endocrinol , vol.260-262 , pp. 137-143
- Jeoung, M.¹ Lee, C.² Ji, I.³ Ji, T.H.⁴

21
- 1842530957
- I. Ji, C. Lee, M. Jeoung, Y. Koo, G. A. Sievert, T. H. Ji, Mol. Endocrinol. 2004, 18, 968- 978.
- (2004) Mol. Endocrinol , vol.18 , pp. 968-978
- Ji, I.¹ Lee, C.² Jeoung, M.³ Koo, Y.⁴ Sievert, G.A.⁵ Ji, T.H.⁶

22
- 85047686522
- I. Ji, C. Lee, Y. Song, P. M. Conn, T. H. Ji, Mol. Endocrinol. 2002, 16, 1299-1308.
- (2002) Mol. Endocrinol , vol.16 , pp. 1299-1308
- Ji, I.¹ Lee, C.² Song, Y.³ Conn, P.M.⁴ Ji, T.H.⁵

23
- 12744280744
- Q. R. Fan, W. A. Hendrickson, Nature 2005, 433, 269 -277.
- (2005) Nature , vol.433 , pp. 269-277
- Fan, Q.R.¹ Hendrickson, W.A.²

24
- 33751243638
- Q. R. Fan, W. A. Hendrickson, Mol. Cell. Endocrinol. 2007, 260-262, 73-82.
- (2007) Mol. Cell. Endocrinol , vol.260-262 , pp. 73-82
- Fan, Q.R.¹ Hendrickson, W.A.²

25
- 34249685481
- K. M. Bonger, R. J. van den Berg, L. H. Heitman, A. P. IJzerman, J. Oosterom, C. M. Timmers, H. S. Overkleeft, G. A. van der Marel, Bioorg. Med. Chem. 2007, 15, 4841 -4856.
- (2007) Bioorg. Med. Chem , vol.15 , pp. 4841-4856
- Bonger, K.M.¹ van den Berg, R.J.² Heitman, L.H.³ IJzerman, A.P.⁴ Oosterom, J.⁵ Timmers, C.M.⁶ Overkleeft, H.S.⁷ van der Marel, G.A.⁸

26
- 33644539496
- S. E. Denmark, S. Venkatraman, J. Org. Chem. 2006, 71, 1668 -1676.
- (2006) J. Org. Chem , vol.71 , pp. 1668-1676
- Denmark, S.E.¹ Venkatraman, S.²

27
- 0032510051
- L. G. Hamann, R. I. Higuchi, L. Zhi, J. P. Edwards, X. N. Wang, K. B. Marschke, J. W. Kong, L. J. Farmer, T. K. Jones, J. Med. Chem. 1998, 41, 623- 639.
- (1998) J. Med. Chem , vol.41 , pp. 623-639
- Hamann, L.G.¹ Higuchi, R.I.² Zhi, L.³ Edwards, J.P.⁴ Wang, X.N.⁵ Marschke, K.B.⁶ Kong, J.W.⁷ Farmer, L.J.⁸ Jones, T.K.⁹

28
- 33744966628
- B. Y. Lee, S. R. Park, H. B. Jeon, K. S. Kim, Tetrahedron Lett. 2006, 47, 5105 -5109.
- (2006) Tetrahedron Lett , vol.47 , pp. 5105-5109
- Lee, B.Y.¹ Park, S.R.² Jeon, H.B.³ Kim, K.S.⁴

29
- 0030444789
- D. E. Koshland, Jr., Curr. Opin. Struct. Biol. 1996, 6, 757- 761.
- (1996) Curr. Opin. Struct. Biol , vol.6 , pp. 757-761
- Koshland Jr., D.E.¹

30
- 73449144629
- M. Mammen, S. K. Choi, G. M. Whitesides, Angew. Chem. 1998, 110, 2908 -2953; Angew. Chem. Int. Ed. 1998, 37, 2755- 2794.
- M. Mammen, S. K. Choi, G. M. Whitesides, Angew. Chem. 1998, 110, 2908 -2953; Angew. Chem. Int. Ed. 1998, 37, 2755- 2794.

31
- 73449091032
- We are aware that the IC50 value we measure for (R/S)-1 deviates from the value we reported earlier.[8] This is likely due to slight variations between the tissue preparations used in the CHO-hFSHR(luc) assay reported earlier[8] and those reported herein.
- We are aware that the IC50 value we measure for (R/S)-1 deviates from the value we reported earlier.[8] This is likely due to slight variations between the tissue preparations used in the CHO-hFSHR(luc) assay reported earlier[8] and those reported herein.

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