SCOPUS 정보 검색 플랫폼

Volumn 22, Issue 10, 2014, Pages 2887-2895

Identification of the stereochemical requirements in the 4-aryl-2-cycloalkylidenhydrazinylthiazole scaffold for the design of selective human monoamine oxidase B inhibitors

(10) D'Ascenzio, Melissa a Carradori, Simone a Secci, Daniela a Mannina, Luisa a,e Sobolev, Anatoly P e De Monte, Celeste a Cirilli, Roberto b Yáñez, Matilde c Alcaro, Stefano d Ortuso, Francesco d

a SAPIENZA UNIVERSITY OF ROME (Italy)

b ISTITUTO SUPERIORE DI SANITÀ (Italy)

c UNIVERSITY OF SANTIAGO DE COMPOSTELA (Spain)

d UNIVERSITY MAGNA GRAECIA OF CATANZARO (Italy)

e CNR (Italy)

Author keywords

Diastereoseparation; Methylcyclopentane; Molecular modeling; Monoamine oxidase inhibitors; Thiazole

Indexed keywords

1 (2 METHYLCYCLOPENTYLIDENE) 2 [4 (4 NITROPHENYL)THIAZOL 2 YL]HYDRAZINE; 1 (3 METHYLCYCLOPENTYLIDENE) 2 [4 (4 NITROPHENYL)THIAZOL 2 YL]HYDRAZINE; 1 [4 (2,4 DIFLUOROPHENYL)THIAZOL 2 YL] 2 (2 METHYLCYCLOPENTYLIDENE)HYDRAZINE; 1 [4 (2,4 DIFLUOROPHENYL)THIAZOL 2 YL] 2 (3 METHYLCYCLOPENTYLIDENE)HYDRAZINE; 1 [4 (4 CYANOPHENYL)THIAZOL 2 YL] 2 (2 METHYLCYCLOPENTYLIDENE)HYDRAZINE; 1 [4 (4 CYANOPHENYL)THIAZOL 2 YL] 2 (3 METHYLCYCLOPENTYLIDENE)HYDRAZINE; 1 [4 (4 FLUOROPHENYL)THIAZOL 2 YL] 2 (2 METHYLCYCLOPENTYLIDENE)HYDRAZINE; 1 [4 (4 FLUOROPHENYL)THIAZOL 2 YL] 2 (3 METHYLCYCLOPENTYLIDENE)HYDRAZINE; CLORGYLINE; IPRONIAZID; ISATIN; MOCLOBEMIDE; MONOAMINE OXIDASE B INHIBITOR; SELEGILINE; UNCLASSIFIED DRUG; AMINE OXIDASE (FLAVIN CONTAINING); ISOENZYME; MONOAMINE OXIDASE INHIBITOR; THIAZOLE DERIVATIVE;

ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DIASTEREOISOMER; DRUG DESIGN; DRUG IDENTIFICATION; DRUG MECHANISM; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO STUDY; STEREOCHEMISTRY; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; HUMANS; ISOENZYMES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 84899498676 PISSN: 09680896 EISSN: 14643391 Source Type: Journal
DOI: 10.1016/j.bmc.2014.03.042 Document Type: Article

Times cited : (24)

References (39)

1
- 84899571106
- D.L. Murphy Biochem. Pharmacol. 1978 1889 27
- (1889) Biochem. Pharmacol. , vol.1978 , pp. 27
- Murphy, D.L.¹

2
- 0024042954
- A.W. Bach, N.C. Lan, D.L. Johnson, C.W. Abell, M.E. Bembenek, S.-W. Kwan, P.H. Seeburg, and J.C. Shih PNAS 85 1988 4934
- (1988) PNAS , vol.85 , pp. 4934
- Bach, A.W.¹ Lan, N.C.² Johnson, D.L.³ Abell, C.W.⁴ Bembenek, M.E.⁵ Kwan, S.-W.⁶ Seeburg, P.H.⁷ Shih, J.C.⁸

3
- 0023942459
- K.N. Westlund, R.M. Denney, R.M. Rose, and C.W. Abell Neuroscience 25 1988 439
- (1988) Neuroscience , vol.25 , pp. 439
- Westlund, K.N.¹ Denney, R.M.² Rose, R.M.³ Abell, C.W.⁴

4
- 34948857723
- D.E. Edmondson, A. Mattevi, C. Binda, M. Li, and F. Hubálek Curr. Med. Chem. 2004 1983 11
- (1983) Curr. Med. Chem. , vol.2004 , pp. 11
- Edmondson, D.E.¹ Mattevi, A.² Binda, C.³ Li, M.⁴ Hubálek, F.⁵

5
- 66149173641
- D.E. Edmondson, C. Binda, J. Wang, A.K. Upadhayay, and A. Mattevi Biochemistry 48 2009 4220
- (2009) Biochemistry , vol.48 , pp. 4220
- Edmondson, D.E.¹ Binda, C.² Wang, J.³ Upadhayay, A.K.⁴ Mattevi, A.⁵

6
- 0032914318
- J.C. Shih, K. Chen, and M.J. Ridd Annu. Rev. Neurosci. 22 1999 197
- (1999) Annu. Rev. Neurosci. , vol.22 , pp. 197
- Shih, J.C.¹ Chen, K.² Ridd, M.J.³

7
- 3242779537
- J.C. Shih, and K. Chen Curr. Med. Chem. 11 2004 1995
- (2004) Curr. Med. Chem. , vol.11 , pp. 1995
- Shih, J.C.¹ Chen, K.²

8
- 38949167692
- L.M. Sayre, G. Perry, and M.A. Smith Chem. Res. Toxicol. 21 2008 172
- (2008) Chem. Res. Toxicol. , vol.21 , pp. 172
- Sayre, L.M.¹ Perry, G.² Smith, M.A.³

9
- 24644441649
- F. Blandini CNS Drug Rev. 11 2005 183
- (2005) CNS Drug Rev. , vol.11 , pp. 183
- Blandini, F.¹

10
- 3242772321
- P. Riederer, L. Lachenmayer, and G. Laux Curr. Med. Chem. 11 2004 2033
- (2004) Curr. Med. Chem. , vol.11 , pp. 2033
- Riederer, P.¹ Lachenmayer, L.² Laux, G.³

11
- 33645307953
- M.B.H. Youdim, D.E. Edmondson, and K.F. Tipton Nat. Rev. 7 2006 295
- (2006) Nat. Rev. , vol.7 , pp. 295
- Youdim, M.B.H.¹ Edmondson, D.E.² Tipton, K.F.³

12
- 51249118269
- M. Bortolato, K. Chen, and J.C. Shih Adv. Drug Deliv. Rev. 60 2008 1527
- (2008) Adv. Drug Deliv. Rev. , vol.60 , pp. 1527
- Bortolato, M.¹ Chen, K.² Shih, J.C.³

13
- 30344432647
- A. Bolasco, R. Fioravanti, and S. Carradori Expert Opin. Ther. Patents 15 2005 1763
- (2005) Expert Opin. Ther. Patents , vol.15 , pp. 1763
- Bolasco, A.¹ Fioravanti, R.² Carradori, S.³

14
- 77953743826
- A. Bolasco, S. Carradori, and R. Fioravanti Expert Opin. Ther. Patents 20 2010 909
- (2010) Expert Opin. Ther. Patents , vol.20 , pp. 909
- Bolasco, A.¹ Carradori, S.² Fioravanti, R.³

15
- 84862867905
- S. Carradori, D. Secci, A. Bolasco, P. Chimenti, and M. D'Ascenzio Expert Opin. Ther. Patents 22 2012 759
- (2012) Expert Opin. Ther. Patents , vol.22 , pp. 759
- Carradori, S.¹ Secci, D.² Bolasco, A.³ Chimenti, P.⁴ D'Ascenzio, M.⁵

16
- 84894081989
- S. Carradori, M. D'Ascenzio, P. Chimenti, D. Secci, and A. Bolasco Mol. Div. 18 2014 219
- (2014) Mol. Div. , vol.18 , pp. 219
- Carradori, S.¹ D'Ascenzio, M.² Chimenti, P.³ Secci, D.⁴ Bolasco, A.⁵

17
- 84879467536
- P. Chimenti, A. Petzer, S. Carradori, M. D'Ascenzio, R. Silvestri, S. Alcaro, F. Ortuso, J.P. Petzer, and D. Secci Eur. J. Med. Chem. 66 2013 221
- (2013) Eur. J. Med. Chem. , vol.66 , pp. 221
- Chimenti, P.¹ Petzer, A.² Carradori, S.³ D'Ascenzio, M.⁴ Silvestri, R.⁵ Alcaro, S.⁶ Ortuso, F.⁷ Petzer, J.P.⁸ Secci, D.⁹

18
- 50249143998
- F. Chimenti, E. Maccioni, D. Secci, A. Bolasco, P. Chimenti, A. Granese, S. Carradori, S. Alcaro, F. Ortuso, M. Yáñez, F. Orallo, R. Cirilli, R. Ferretti, and F. La Torre J. Med. Chem. 51 2008 4874
- (2008) J. Med. Chem. , vol.51 , pp. 4874
- Chimenti, F.¹ Maccioni, E.² Secci, D.³ Bolasco, A.⁴ Chimenti, P.⁵ Granese, A.⁶ Carradori, S.⁷ Alcaro, S.⁸ Ortuso, F.⁹ Yáñez, M.¹⁰ Orallo, F.¹¹ Cirilli, R.¹² Ferretti, R.¹³ La Torre, F.¹⁴

19
- 66349115617
- F. Chimenti, S. Carradori, D. Secci, A. Bolasco, P. Chimenti, A. Granese, and B. Bizzarri J. Heterocycl. Chem. 46 2009 575
- (2009) J. Heterocycl. Chem. , vol.46 , pp. 575
- Chimenti, F.¹ Carradori, S.² Secci, D.³ Bolasco, A.⁴ Chimenti, P.⁵ Granese, A.⁶ Bizzarri, B.⁷

20
- 77955325332
- F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, A. Granese, S. Carradori, E. Maccioni, M.C. Cardia, M. Yáñez, F. Orallo, S. Alcaro, F. Ortuso, R. Cirilli, R. Ferretti, S. Distinto, J. Kirchmair, and T. Langer Bioorg. Med. Chem. 18 2010 5063
- (2010) Bioorg. Med. Chem. , vol.18 , pp. 5063
- Chimenti, F.¹ Secci, D.² Bolasco, A.³ Chimenti, P.⁴ Granese, A.⁵ Carradori, S.⁶ Maccioni, E.⁷ Cardia, M.C.⁸ Yáñez, M.⁹ Orallo, F.¹⁰ Alcaro, S.¹¹ Ortuso, F.¹² Cirilli, R.¹³ Ferretti, R.¹⁴ Distinto, S.¹⁵ Kirchmair, J.¹⁶ Langer, T.¹⁷

21
- 77955418391
- F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, A. Granese, S. Carradori, M. Yáñez, F. Orallo, F. Ortuso, and S. Alcaro Bioorg. Med. Chem. 18 2010 5715
- (2010) Bioorg. Med. Chem. , vol.18 , pp. 5715
- Chimenti, F.¹ Secci, D.² Bolasco, A.³ Chimenti, P.⁴ Granese, A.⁵ Carradori, S.⁶ Yáñez, M.⁷ Orallo, F.⁸ Ortuso, F.⁹ Alcaro, S.¹⁰

22
- 77956325073
- F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, A. Granese, S. Carradori, M. D'Ascenzio, M. Yáñez, and F. Orallo Med. Chem. Commun. 1 2010 61
- (2010) Med. Chem. Commun. , vol.1 , pp. 61
- Chimenti, F.¹ Secci, D.² Bolasco, A.³ Chimenti, P.⁴ Granese, A.⁵ Carradori, S.⁶ D'Ascenzio, M.⁷ Yáñez, M.⁸ Orallo, F.⁹

23
- 77956305471
- F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, A. Granese, S. Carradori, M. Yáñez, F. Orallo, M.L. Sanna, B. Gallinella, and R. Cirilli J. Med. Chem. 53 2010 6516
- (2010) J. Med. Chem. , vol.53 , pp. 6516
- Chimenti, F.¹ Secci, D.² Bolasco, A.³ Chimenti, P.⁴ Granese, A.⁵ Carradori, S.⁶ Yáñez, M.⁷ Orallo, F.⁸ Sanna, M.L.⁹ Gallinella, B.¹⁰ Cirilli, R.¹¹

24
- 84868676600
- D. Secci, A. Bolasco, S. Carradori, M. D'Ascenzio, R. Nescatelli, and M. Yáñez Eur. J. Med. Chem. 58 2012 405
- (2012) Eur. J. Med. Chem. , vol.58 , pp. 405
- Secci, D.¹ Bolasco, A.² Carradori, S.³ D'Ascenzio, M.⁴ Nescatelli, R.⁵ Yáñez, M.⁶

25
- 84872226218
- S. Carradori, M. D'Ascenzio, C. De Monte, D. Secci, and M. Yáñez Arch. Pharm. Life Sci. 346 2013 17
- (2013) Arch. Pharm. Life Sci. , vol.346 , pp. 17
- Carradori, S.¹ D'Ascenzio, M.² De Monte, C.³ Secci, D.⁴ Yáñez, M.⁵

26
- 84986870251
- R. Benassi, A. Benedetti, F. Taddei, R. Cappelletti, D. Nardi, and A. Tajana Org. Magn. Reson. 20 1982 26
- (1982) Org. Magn. Reson. , vol.20 , pp. 26
- Benassi, R.¹ Benedetti, A.² Taddei, F.³ Cappelletti, R.⁴ Nardi, D.⁵ Tajana, A.⁶

27
- 35648952796
- R. Cirilli, R. Ferretti, F. La Torre, D. Secci, A. Bolasco, S. Carradori, and M. Pierini J. Chromatogr. A 1172 2007 160
- (2007) J. Chromatogr. A , vol.1172 , pp. 160
- Cirilli, R.¹ Ferretti, R.² La Torre, F.³ Secci, D.⁴ Bolasco, A.⁵ Carradori, S.⁶ Pierini, M.⁷

28
- 84870314704
- S. Carradori, R. Cirilli, S. Dei Cicchi, R. Ferretti, S. Menta, M. Pierini, and D. Secci J. Chromatogr. A 1269 2012 168
- (2012) J. Chromatogr. A , vol.1269 , pp. 168
- Carradori, S.¹ Cirilli, R.² Dei Cicchi, S.³ Ferretti, R.⁴ Menta, S.⁵ Pierini, M.⁶ Secci, D.⁷

29
- 33646092535
- M. Yáñez, N. Fraiz, E. Cano, and F. Orallo Biochem. Biophys. Res. Commun. 344 2006 688
- (2006) Biochem. Biophys. Res. Commun. , vol.344 , pp. 688
- Yáñez, M.¹ Fraiz, N.² Cano, E.³ Orallo, F.⁴

30
- 84899579942
- Schrödinger, LLC; New York, NY
- Schrödinger, LLC; New York, NY, 2013. http://www.schrodinger.com.
- (2013)

31
- 0033954256
- H.M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T.N. Bhat, H. Weissig, I.N. Shindyalov, and P.E. Bourne Nucleic Acids Res. 28 2000 235
- (2000) Nucleic Acids Res. , vol.28 , pp. 235
- Berman, H.M.¹ Westbrook, J.² Feng, Z.³ Gilliland, G.⁴ Bhat, T.N.⁵ Weissig, H.⁶ Shindyalov, I.N.⁷ Bourne, P.E.⁸

32
- 44449117421
- S.Y. Son, J. Ma, Y. Kondou, M. Yoshimura, E. Yamashita, and T. Tsukihara Proc. Natl. Acad. Sci. U.S.A. 105 2008 5739
- (2008) Proc. Natl. Acad. Sci. U.S.A. , vol.105 , pp. 5739
- Son, S.Y.¹ Ma, J.² Kondou, Y.³ Yoshimura, M.⁴ Yamashita, E.⁵ Tsukihara, T.⁶

33
- 36148955400
- C. Binda, J. Wang, L. Pisani, C. Caccia, A. Carotti, P. Salvati, D.E. Edmondson, and A. Mattevi J. Med. Chem. 50 2007 5848
- (2007) J. Med. Chem. , vol.50 , pp. 5848
- Binda, C.¹ Wang, J.² Pisani, L.³ Caccia, C.⁴ Carotti, A.⁵ Salvati, P.⁶ Edmondson, D.E.⁷ Mattevi, A.⁸

34
- 0035913529
- G.A. Kaminski, R.A. Friesner, J. Tirado-Rives, and W.J. Jorgensen J. Phys. Chem. B 105 2001 6474
- (2001) J. Phys. Chem. B , vol.105 , pp. 6474
- Kaminski, G.A.¹ Friesner, R.A.² Tirado-Rives, J.³ Jorgensen, W.J.⁴

35
- 0001308921
- W. Hasel, T.F. Hendrickson, and W.C. Still Tetrahedron Comput. Methodol. 1 1988 103
- (1988) Tetrahedron Comput. Methodol. , vol.1 , pp. 103
- Hasel, W.¹ Hendrickson, T.F.² Still, W.C.³

36
- 33750124980
- R.A. Friesner, R.B. Murphy, M.P. Repasky, L.L. Frye, J.R. Greenwood, T.A. Halgren, P.C. Sanschagrin, and D.T. Mainz J. Med. Chem. 49 2006 6177
- (2006) J. Med. Chem. , vol.49 , pp. 6177
- Friesner, R.A.¹ Murphy, R.B.² Repasky, M.P.³ Frye, L.L.⁴ Greenwood, J.R.⁵ Halgren, T.A.⁶ Sanschagrin, P.C.⁷ Mainz, D.T.⁸

37
- 1642310340
- T.A. Halgren, R.B. Murphy, R.A. Friesner, H.S. Beard, L.L. Frye, W.T. Pollard, and J.L. Banks J. Med. Chem. 47 2004 1750
- (2004) J. Med. Chem. , vol.47 , pp. 1750
- Halgren, T.A.¹ Murphy, R.B.² Friesner, R.A.³ Beard, H.S.⁴ Frye, L.L.⁵ Pollard, W.T.⁶ Banks, J.L.⁷

38
- 12144289984
- R.A. Friesner, J.L. Banks, R.B. Murphy, T.A. Halgren, J.J. Klicic, D.T. Mainz, M.P. Repasky, E.H. Knoll, D.E. Shaw, M. Shelley, J.K. Perry, P. Francis, and P.S. Shenkin J. Med. Chem. 47 2004 1739
- (2004) J. Med. Chem. , vol.47 , pp. 1739
- 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, E.H.⁸ Shaw, D.E.⁹ Shelley, M.¹⁰ Perry, J.K.¹¹ Francis, P.¹² Shenkin, P.S.¹³

39
- 84871301540
- LLC
- The PyMOL Molecular Graphics System, Version 1.3 Schrödinger, LLC. http://www.schrodinger.com.
- The PyMOL Molecular Graphics System, Version 1.3 Schrödinger

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.