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Volumn 2, Issue 12, 2007, Pages 1741-1749

Synthesis, enantiomeric resolution, and structure-activity relationship study of a series of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene MT2 receptor antagonists

(12) Spadoni, Gilberto b Bedini, Annalida b Diamantini, Giuseppe b Tarzia, Giorgio b Rivara, Silvia a Lorenzi, Simone a Lodola, Alessio a Mor, Marco a Lucini, Valeria c Pannacci, Marilou c Caronno, Alessia c Fraschini, Franco c

a UNIVERSITY OF PARMA (Italy)

b UNIVERSITY OF URBINO (Italy)

c UNIVERSITY OF MILAN (Italy)

Author keywords

Docking; Medicinal chemistry; Melatonin; MT2 antagonists; Structure activity relationships

Indexed keywords

10,11 DIHYDRO 5H DIBENZO(A,D)CYCLOHEPTENE; 10,11-DIHYDRO-5H-DIBENZO(A,D)CYCLOHEPTENE; CYCLOHEPTANE DERIVATIVE; MELATONIN 2 RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL; ARTICLE; CELL STRAIN 3T3; CHEMISTRY; DRUG ANTAGONISM; ELECTROSPRAY MASS SPECTROMETRY; INFRARED SPECTROPHOTOMETRY; MOUSE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STEREOISOMERISM;

ANIMALS; CYCLOHEPTANES; MAGNETIC RESONANCE SPECTROSCOPY; MICE; NIH 3T3 CELLS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTOR, MELATONIN, MT2; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM;

EID: 48849104646 PISSN: 18607179 EISSN: 18607187 Source Type: Journal
DOI: 10.1002/cmdc.200700141 Document Type: Article

Times cited : (13)

References (42)

1
- 33947460818
- A. Lerner, J. D. Case, Y. Takahashi, J. Am. Chem. Soc. 1958, 80, 2587.
- (1958) J. Am. Chem. Soc , vol.80 , pp. 2587
- Lerner, A.¹ Case, J.D.² Takahashi, Y.³

2
- 22544455330
- J. Arendt, J. Biol. Rhythms 2005, 20, 291-303.
- (2005) J. Biol. Rhythms , vol.20 , pp. 291-303
- Arendt, J.¹

3
- 4344638051
- J. Barrenetxe, P. Delagrange, J. A. Martínez, J. Physiol. Biochem. 2004, 60, 61-72.
- (2004) J. Physiol. Biochem , vol.60 , pp. 61-72
- Barrenetxe, J.¹ Delagrange, P.² Martínez, J.A.³

4
- 33745205104
- S. R. Pandi-Perumal, V. Srinivasan, G. J. M. Maestroni, D. P. Cardinali, B. Poeggeler, R. Hardeland, FEBS J. 2006, 273, 2813-2838.
- (2006) FEBS J , vol.273 , pp. 2813-2838
- Pandi-Perumal, S.R.¹ Srinivasan, V.² Maestroni, G.J.M.³ Cardinali, D.P.⁴ Poeggeler, B.⁵ Hardeland, R.⁶

5
- 2942580561
- a) M. L. Dubocovich, M. A. Rivera-Bermudez, M. J. Gerdin, M. I. Masana, Front. Biosci. 2003, 8, 1093-1108;
- (2003) Front. Biosci , vol.8 , pp. 1093-1108
- Dubocovich, M.L.¹ Rivera-Bermudez, M.A.² Gerdin, M.J.³ Masana, M.I.⁴

6
- 0242301704
- b) P. Barrett, S. Conway, P. J. Morgan, J. Pineal Res. 2003, 35, 221-230.
- (2003) J. Pineal Res , vol.35 , pp. 221-230
- Barrett, P.¹ Conway, S.² Morgan, P.J.³

7
- 0035991404
- C. von Gall, J. H. Stehle, D. R. Weaver, Cell Tissue Res. 2002, 309, 151-162.
- (2002) Cell Tissue Res , vol.309 , pp. 151-162
- von Gall, C.¹ Stehle, J.H.² Weaver, D.R.³

8
- 28244496559
- F. Mailliet, G. Ferry, F. Vella, S. Berger, F. Cogé, P. Chomarat, C. Mallet, S.-P. Guénin, G. Guillaumet, M.-C. Viaud-Massuard, S. Yous, P. Delagrange, J. A. Boutin, Biochem. Pharmacol. 2005, 71, 74-88.
- (2005) Biochem. Pharmacol , vol.71 , pp. 74-88
- Mailliet, F.¹ Ferry, G.² Vella, F.³ Berger, S.⁴ Cogé, F.⁵ Chomarat, P.⁶ Mallet, C.⁷ Guénin, S.-P.⁸ Guillaumet, G.⁹ Viaud-Massuard, M.-C.¹⁰ Yous, S.¹¹ Delagrange, P.¹² Boutin, J.A.¹³

9
- 33645402334
- C. Ekmekcioglu, Biomed. Pharmacother. 2006, 60, 97-108.
- (2006) Biomed. Pharmacother , vol.60 , pp. 97-108
- Ekmekcioglu, C.¹

10
- 27644449587
- M. L. Dubocovich, M. Markowska, Endocrine 2005, 27, 101-110.
- (2005) Endocrine , vol.27 , pp. 101-110
- Dubocovich, M.L.¹ Markowska, M.²

11
- 21844433213
- Chem. Sci. Ed
- D. P. Zlotos, Arch. Pharm. Chem. Sci. Ed. 2005, 338, 229-247.
- (2005) Arch. Pharm , vol.338 , pp. 229-247
- Zlotos, D.P.¹

12
- 33444465365
- L. R. Fitzgerald, J. E. Reed, Annu. Rep. Med. Chem. 2004, 39, 25-37.
- (2004) Annu. Rep. Med. Chem , vol.39 , pp. 25-37
- Fitzgerald, L.R.¹ Reed, J.E.²

13
- 33645981919
- S. Rivara, M. Mor, S. Lorenzi, A. Lodola, P. V. Plazzi, G. Spadoni, A. Bedini, G. Tarzia, Arkivoc. 2006, viii, 8-16.
- (2006) Arkivoc , vol.8 , pp. 8-16
- Rivara, S.¹ Mor, M.² Lorenzi, S.³ Lodola, A.⁴ Plazzi, P.V.⁵ Spadoni, G.⁶ Bedini, A.⁷ Tarzia, G.⁸

14
- 0038303310
- V. Audinot, F. Maillet, C. Lahaye-Brasseur, A. Bonnaud, A. Le Gall, C. Amossé, S. Dromaint, M. Rodriguez, N. Nagel, J.-P. Galizzi, B. Malpaux, G. Guillaumet, D. Lesieur, F. Lefoulon, P. Renard, P. Delagrange, J. A. Boutin, Naunyn-Schmiedeberg's Arch. Pharmacol. 2003, 367, 553-561.
- (2003) Naunyn-Schmiedeberg's Arch. Pharmacol , vol.367 , pp. 553-561
- Audinot, V.¹ Maillet, F.² Lahaye-Brasseur, C.³ Bonnaud, A.⁴ Le Gall, A.⁵ Amossé, C.⁶ Dromaint, S.⁷ Rodriguez, M.⁸ Nagel, N.⁹ Galizzi, J.-P.¹⁰ Malpaux, B.¹¹ Guillaumet, G.¹² Lesieur, D.¹³ Lefoulon, F.¹⁴ Renard, P.¹⁵ Delagrange, P.¹⁶ Boutin, J.A.¹⁷

15
- 0035974703
- G. Spadoni, C. Balsamini, G. Diamantini, A. Tontini, G. Tarzia, M. Mor, S. Rivara, P. V. Plazzi, R. Nonno, V. Lucini, M. Pannacci, F. Fraschini, B. M. Stankov, J. Med. Chem. 2001, 44, 2900-2912.
- (2001) J. Med. Chem , vol.44 , pp. 2900-2912
- Spadoni, G.¹ Balsamini, C.² Diamantini, G.³ Tontini, A.⁴ Tarzia, G.⁵ Mor, M.⁶ Rivara, S.⁷ Plazzi, P.V.⁸ Nonno, R.⁹ Lucini, V.¹⁰ Pannacci, M.¹¹ Fraschini, F.¹² Stankov, B.M.¹³

16
- 0037431390
- S. Rivara, M. Mor, C. Silva, V. Zuliani, F. Vacondio, G. Spadoni, A. Bedini, G. Tarzia, V. Lucini, M. Pannacci, F. Fraschini, P. V. Plazzi, J. Med. Chem. 2003, 46, 1429-1439.
- (2003) J. Med. Chem , vol.46 , pp. 1429-1439
- Rivara, S.¹ Mor, M.² Silva, C.³ Zuliani, V.⁴ Vacondio, F.⁵ Spadoni, G.⁶ Bedini, A.⁷ Tarzia, G.⁸ Lucini, V.⁹ Pannacci, M.¹⁰ Fraschini, F.¹¹ Plazzi, P.V.¹²

17
- 3843069978
- V. Lucini, M. Pannacci, F. Scaglione, S. Rivara, M. Mor, F. Bordi, P. V. Plazzi, G. Spadoni, A. Bedini, G. Piersanti, G. Diamantini, G. Tarzia, J. Med. Chem. 2004, 47, 4202-4212.
- (2004) J. Med. Chem , vol.47 , pp. 4202-4212
- Lucini, V.¹ Pannacci, M.² Scaglione, F.³ Rivara, S.⁴ Mor, M.⁵ Bordi, F.⁶ Plazzi, P.V.⁷ Spadoni, G.⁸ Bedini, A.⁹ Piersanti, G.¹⁰ Diamantini, G.¹¹ Tarzia, G.¹²

18
- 20444363062
- S. Rivara, S. Lorenzi, M. Mor, P. V. Plazzi, G. Spadoni, A. Bedini, G. Tarzia, J. Med. Chem. 2005, 48, 4049-4060.
- (2005) J. Med. Chem , vol.48 , pp. 4049-4060
- Rivara, S.¹ Lorenzi, S.² Mor, M.³ Plazzi, P.V.⁴ Spadoni, G.⁵ Bedini, A.⁶ Tarzia, G.⁷

19
- 0027773051
- Y. Liu, H. Yu, B. E. Svensson, L. Cortizo, T. Lewander, U. Hacksell, J. Med. Chem. 1993, 36, 4221-4229.
- (1993) J. Med. Chem , vol.36 , pp. 4221-4229
- Liu, Y.¹ Yu, H.² Svensson, B.E.³ Cortizo, L.⁴ Lewander, T.⁵ Hacksell, U.⁶

20
- 26844485913
- E. Yashima, C. Yamamoto, Y. Okamoto, Synlett 1998, 344-360.
- (1998) Synlett , pp. 344-360
- Yashima, E.¹ Yamamoto, C.² Okamoto, Y.³

21
- 0028148647
- J. M. Jansen, S. Copinga, G. Gruppen, R. Isaksson, D. T. Witte, C. J. Grol, Chirality 1994, 6, 596-604.
- (1994) Chirality , vol.6 , pp. 596-604
- Jansen, J.M.¹ Copinga, S.² Gruppen, G.³ Isaksson, R.⁴ Witte, D.T.⁵ Grol, C.J.⁶

22
- 33645919613
- S. Rivara, G. Diamantini, B. Di Giacomo, D. Lamba, G. Gatti, V. Lucini, M. Pannacci, M. Mor, G. Spadoni, G. Tarzia, Bioorg. Med. Chem. 2006, 14, 3383-3391.
- (2006) Bioorg. Med. Chem , vol.14 , pp. 3383-3391
- Rivara, S.¹ Diamantini, G.² Di Giacomo, B.³ Lamba, D.⁴ Gatti, G.⁵ Lucini, V.⁶ Pannacci, M.⁷ Mor, M.⁸ Spadoni, G.⁹ Tarzia, G.¹⁰

23
- 0037142332
- V. Wallez, S. Durieux-Poissonnier, P. Chavatte, J. A. Boutin, V. Audinot, J.-P. Nicolas, C. Bennejean, P. Delagrange, P. Renard, D. Lesieur, J. Med. Chem. 2002, 45, 2788-2800.
- (2002) J. Med. Chem , vol.45 , pp. 2788-2800
- Wallez, V.¹ Durieux-Poissonnier, S.² Chavatte, P.³ Boutin, J.A.⁴ Audinot, V.⁵ Nicolas, J.-P.⁶ Bennejean, C.⁷ Delagrange, P.⁸ Renard, P.⁹ Lesieur, D.¹⁰

24
- 1242271965
- L.-Q. Sun, J. Chen, K. Takaki, G. Johnson, L. Iben, C. D. Mahle, E. Ryan, C. Xu, Bioorg. Med. Chem. Lett. 2004, 14, 1197-1200.
- (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 1197-1200
- Sun, L.-Q.¹ Chen, J.² Takaki, K.³ Johnson, G.⁴ Iben, L.⁵ Mahle, C.D.⁶ Ryan, E.⁷ Xu, C.⁸

25
- 7044254907
- G. N. Karageorge, S. Bertenshaw, L. Iben, C. Xu, N. Sarbin, A. Gentile, G. M. Dubowchik, Bioorg. Med. Chem. Lett. 2004, 14, 5881-5884.
- (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 5881-5884
- Karageorge, G.N.¹ Bertenshaw, S.² Iben, L.³ Xu, C.⁴ Sarbin, N.⁵ Gentile, A.⁶ Dubowchik, G.M.⁷

26
- 0028909154
- D. Sugden, N. W. S. Chong, D. F. V. Lewis, Br. J. Pharmacol. 1995, 114, 618-623.
- (1995) Br. J. Pharmacol , vol.114 , pp. 618-623
- Sugden, D.¹ Chong, N.W.S.² Lewis, D.F.V.³

27
- 0031725325
- V. Leclerc, E. Fourmaintraux, P. Depreux, D. Lesieur, P. Morgan, H. E. Howell, P. Renard, D.-H. Caignard, B. Pfeiffer, P. Delagrange, B. Guardiola-Lemaitre, J. Andrieux, Bioorg. Med. Chem. 1998, 6, 1875-1887.
- (1998) Bioorg. Med. Chem , vol.6 , pp. 1875-1887
- Leclerc, V.¹ Fourmaintraux, E.² Depreux, P.³ Lesieur, D.⁴ Morgan, P.⁵ Howell, H.E.⁶ Renard, P.⁷ Caignard, D.-H.⁸ Pfeiffer, B.⁹ Delagrange, P.¹⁰ Guardiola-Lemaitre, B.¹¹ Andrieux, J.¹²

28
- 0037463810
- R. J. Mattson, J. D. Catt, D. Keavy, C. P. Sloan, J. Epperson, Q. Gao, D. B. Hodges, L. Iben, C. D. Mahle, E. Ryan, F. D. Yocca, Bioorg. Med. Chem. Lett. 2003, 13, 1199-1202.
- (2003) Bioorg. Med. Chem. Lett , vol.13 , pp. 1199-1202
- Mattson, R.J.¹ Catt, J.D.² Keavy, D.³ Sloan, C.P.⁴ Epperson, J.⁵ Gao, Q.⁶ Hodges, D.B.⁷ Iben, L.⁸ Mahle, C.D.⁹ Ryan, E.¹⁰ Yocca, F.D.¹¹

29
- 0030964398
- M. L. Dubocovich, M. I. Masana, S. Iacob, D. M. Sauri, Naunyn-Schmiedeberg's Arch. Pharmacol. 1997, 355, 365-375.
- (1997) Naunyn-Schmiedeberg's Arch. Pharmacol , vol.355 , pp. 365-375
- Dubocovich, M.L.¹ Masana, M.I.² Iacob, S.³ Sauri, D.M.⁴

30
- 0033786778
- R. Nonno, V. Lucini, G. Spadoni, M. Pannacci, A. Croce, D. Esposti, C. Balsamini, G. Tarzia, F. Fraschini, B. M. Stankov, J. Pineal Res. 2000, 29, 234-240.
- (2000) J. Pineal Res , vol.29 , pp. 234-240
- Nonno, R.¹ Lucini, V.² Spadoni, G.³ Pannacci, M.⁴ Croce, A.⁵ Esposti, D.⁶ Balsamini, C.⁷ Tarzia, G.⁸ Fraschini, F.⁹ Stankov, B.M.¹⁰

31
- 12144289984
- R. A. Friesner, J. L. Banks, R. B. Murphy, T. A. Halgren, J. J. Klicic, D. T. Mainz, M. P. Repasky, H. E. Knoll, M. Shelley, J. E. Perry, D. E. Shaw, P. Francis, P. S. Shenkin, J. Med. Chem. 2004, 47, 1739-1749.
- (2004) J. Med. Chem , vol.47 , pp. 1739-1749
- Friesner, R.A.¹ Banks, J.L.² Murphy, R.B.³ Halgren, T.A.⁴ Klicic, J.J.⁵ Mainz, D.T.⁶ Repasky, M.P.⁷ Knoll, H.E.⁸ Shelley, M.⁹ Perry, J.E.¹⁰ Shaw, D.E.¹¹ Francis, P.¹² Shenkin, P.S.¹³

32
- 0033002220
- G. Spadoni, M. Mor, G. Tarzia, Biol. Signals Recept. 1999, 8, 15-23.
- (1999) Biol. Signals Recept , vol.8 , pp. 15-23
- Spadoni, G.¹ Mor, M.² Tarzia, G.³

33
- 0034704888
- R. Faust, P. J. Garratt, R. Jones, L.-K. Yeh, A. Tsotinis, M. Panoussopoulou, T. Calogeropoulou, M.-T. Teh, D. Sugden, J. Med. Chem. 2000, 43, 1050-1061.
- (2000) J. Med. Chem , vol.43 , pp. 1050-1061
- Faust, R.¹ Garratt, P.J.² Jones, R.³ Yeh, L.-K.⁴ Tsotinis, A.⁵ Panoussopoulou, M.⁶ Calogeropoulou, T.⁷ Teh, M.-T.⁸ Sugden, D.⁹

34
- 0031801678
- R. Nonno, V. Lucini, M. Pannacci, C. Mazzucchelli, D. Angeloni, F. Fraschini, B. M. Stankov, Br. J. Pharmacol. 1998, 124, 485-492.
- (1998) Br. J. Pharmacol , vol.124 , pp. 485-492
- Nonno, R.¹ Lucini, V.² Pannacci, M.³ Mazzucchelli, C.⁴ Angeloni, D.⁵ Fraschini, F.⁶ Stankov, B.M.⁷

35
- 0032812567
- R. Nonno, M. Pannacci, V. Lucini, D. Angeloni, F. Fraschini, B. M. Stankov, Br. J. Pharmacol. 1999, 127, 1288-1294.
- (1999) Br. J. Pharmacol , vol.127 , pp. 1288-1294
- Nonno, R.¹ Pannacci, M.² Lucini, V.³ Angeloni, D.⁴ Fraschini, F.⁵ Stankov, B.M.⁶

36
- 0017184389
- M. M. Bradford, Anal. Biochem. 1976, 72, 248-254.
- (1976) Anal. Biochem , vol.72 , pp. 248-254
- Bradford, M.M.¹

37
- 0015861774
- Y.-C. Cheng, W. H. Prusoff, Biochem. Pharmacol. 1973, 22, 3099-3108.
- (1973) Biochem. Pharmacol , vol.22 , pp. 3099-3108
- Cheng, Y.-C.¹ Prusoff, W.H.²

38
- 14444284336
- G. Spadoni, C. Balsamini, A. Bedini, G. Diamantini, B. Di Giacomo, A. Tontini, G. Tarzia, M. Mor, P. V. Plazzi, S. Rivara, R. Nonno, M. Pannacci, V. Lucini, F. Fraschini, B. M. Stankov, J. Med. Chem. 1998, 41, 3624-3634.
- (1998) J. Med. Chem , vol.41 , pp. 3624-3634
- Spadoni, G.¹ Balsamini, C.² Bedini, A.³ Diamantini, G.⁴ Di Giacomo, B.⁵ Tontini, A.⁶ Tarzia, G.⁷ Mor, M.⁸ Plazzi, P.V.⁹ Rivara, S.¹⁰ Nonno, R.¹¹ Pannacci, M.¹² Lucini, V.¹³ Fraschini, F.¹⁴ Stankov, B.M.¹⁵

39
- 5544242529
- T. A. Halgren, J. Comput. Chem. 1999, 20, 720-729.
- (1999) J. Comput. Chem , vol.20 , pp. 720-729
- Halgren, T.A.¹

40
- 54549100793
- Macromodel 8.6, Schrödinger LLC, New York, NY (USA).
- Macromodel 8.6, Schrödinger LLC, New York, NY (USA).

41
- 54549119733
- Sybyl 7.2, Tripos Inc., 1699 South Hanley Rd., St. Louis, MO, 63144 (USA).
- Sybyl 7.2, Tripos Inc., 1699 South Hanley Rd., St. Louis, MO, 63144 (USA).

42
- 0037571112
- T. A. Halgren, J. Comput. Chem. 1996, 17, 490-519.
- (1996) J. Comput. Chem , vol.17 , pp. 490-519
- Halgren, T.A.¹

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