Design, synthesis, pharmacological evaluation and computational studies of 1-(biphenyl-4-yl)-2-[4-(substituted phenyl)-piperazin-1-yl]ethanones as potential antipsychotics

European Journal of Medicinal Chemistry

Volumn 74, Issue , 2014, Pages 358-365

  Bhosale, Sharad H ^a   Kanhed, Ashish M ^a   Dash, Radha Charan ^a   Suryawanshi, Mugdha R ^a   Mahadik, K R ^a  

^a BHARATI VIDYAPEETH DEEMED UNIVERSITY   (India)

Author keywords

1 (Biphenyl 4 yl) 2 4 (substituted phenyl) piperazin 1 yl ethanones; Antipsychotic; Descriptor based similarity study; Pharmacological evaluation; QSAR

Indexed keywords

1 (BIPHENYL 4 YL) 2 (4 M TOLYL PIPERAZIN 1 YL)ETHANONE; 1 (BIPHENYL 4 YL) 2 (4 O TOLYLPIPERAZIN 1 YL)ETHANONE; 1 (BIPHENYL 4 YL) 2 (4 P TOLYL PIPERAZIN 1 YL)ETHANONE; 1 (BIPHENYL 4 YL) 2 (4 PHENYL PIPERAZIN 1 YL)ETHANONE; 1 (BIPHENYL 4 YL) 2 [4 (2 CHLOROPHENYL)PIPERAZIN 1 YL]ETHANONE; 1 (BIPHENYL 4 YL) 2 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]ETHANONE; 1 (BIPHENYL 4 YL) 2 [4 (2,3 DICHLOROPHENYL)PIPERAZIN 1 YL]ETHANONE; 1 (BIPHENYL 4 YL) 2 [4 (2,3 DIMETHYLPHENYL)PIPERAZIN 1 YL]ETHANONE; 1 (BIPHENYL 4 YL) 2 [4 (3 CHLOROPHENYL)PIPERAZIN 1 YL]ETHANONE; 1 (BIPHENYL 4 YL) 2 [4 (3 TRIFLUROMETHYLPHENYL)PIPERAZIN 1 YL]ETHANONE; 1 (BIPHENYL 4 YL) 2 [4 (3,4 DICHLOROPHENYL)PIPERAZIN 1 YL]ETHANONE; 1 (BIPHENYL 4 YL) 2 [4 (4 CHLOROPHENYL)PIPERAZIN 1 YL]ETHANONE; 1 (BIPHENYL 4 YL) 2 [4 (4 FLUROPHENYL)PIPERAZIN 1 YL]ETHANONE; 1 (BIPHENYL 4 YL) 2 [4 (4 METHOXYPHENYL)PIPERAZIN 1 YL]ETHANONE; APOMORPHINE; ARIPIPRAZOLE; DOPAMINE 2 RECEPTOR; HALOPERIDOL; NEUROLEPTIC AGENT; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL BEHAVIOR; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIDOPAMINERGIC ACTIVITY; ANTISEROTONERGIC ACTIVITY; ARTICLE; CLIMBING; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HALOPERIDOL-INDUCED CATALEPSY; HEAD TWITCH; MALE; MASS SPECTROMETRY; MOLECULAR DOCKING; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT; REARING;

1-(BIPHENYL-4-YL)-2-[4-(SUBSTITUTED PHENYL)-PIPERAZIN-1-YL]ETHANONES; ANTIPSYCHOTIC; DESCRIPTOR BASED SIMILARITY STUDY; PHARMACOLOGICAL EVALUATION; QSAR;

ANTIPSYCHOTIC AGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR DOCKING SIMULATION; PIPERAZINES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84893420171     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.12.043     Document Type: Article

References (27)

1. J.S. Mayer, and L.F. Quenzer Psychopharmacology: Drugs, the Brain and Behavior 2005 Sinauer Associates Inc. Sunderland, Massachusetts, USA
2. B. Capuano, I.T. Crosby, and E.J. Lloyd Schizophrenia: genesis, receptorology and current therapeutics Curr. Med. Chem. 9 5 2002 521 548 (Pubitemid 34436433)
3. S. Aldridge Magic Molecules: How Drugs Works 1998 Cambridge University Press
4. S. Wu, R. Gao, Q. Xing, H. Li, Y. Shen, N. Gu, G. Feng, and L. He Association of DRD2 polymorphisms and chlorpromazine-induced extrapyramidal syndrome in Chinese schizophrenic patients Acta Pharmacol. Sin. 27 8 2006 966 970 (Pubitemid 44127903)
5. A. Wieck, and P. Haddad Hyperprolactinaemia caused by antipsychotic drugs BMJ 324 7332 2002 250 252 (Pubitemid 34121831)
6. B.H. Hansen, B.V. Christensen, F.C. Gronvald, and J.P. Mongensen Mesolimbic selective antipsychotic arylcarbamates Eur. J. Med. Chem. 33 11 1998 839 858 (Pubitemid 29533408)
7. S. Kapur, and G. Remington Serotonin-dopamine interaction and its relevance to schizophrenia Am. J. Psychiatry 153 1996 466 476 (Pubitemid 26113309)
8. D.A. Wirshing, W.C. Wirshing, L. Kysar, M.A. Berisford, D. Goldstein, J. Pashdag, J. Mintz, and S.R. Marder Novel antipsychotics: comparison of weight gain liabilities J. Clin. Psychiatry 60 6 1999 358 363 (Pubitemid 29289721)
9. M. Lorenz, W.E. Evering, A. Provencher, J.T. Blue, H.B. Lewis, J.R. Hazelette, P. Rajagopalan, P.C. Meunier, and B.D. Car Atypical antipsychotic-induced neutropenia in dogs Toxicol. Appl. Pharmacol. 155 3 1999 227 236 (Pubitemid 29153370)
10. J.A. Lowe, T.F. Seeger, A.A. Nagel, H.R. Howard, P.A. Seymour, J.H.Heym, F.E. Ewing, M.E. Newman, A.W. Schmidt, and J.S. Furman 1-Naphthylpiperazine derivatives as potential atypical antipsychotic agents J. Med. Chem. 34 6 1991 1860 1866
11. R.W. Feenstra, J. Moes, J.J. Hofma, H. Kling, W. Kuipers, S.K. Long, and M.M. Tulp New 1-aryl-4-(biarylmethylene)piperazines as potential atypical antipsychotics sharing dopamine D2-receptor and serotonin 5-HT1A-receptor affinities Bioorg. Med. Chem. Lett. 11 2001 2345 2349 (Pubitemid 32781696)
12. G.E. Martin, R.J. Elgin, J.R. Mathiasen, C.B. Davis, J.M. Kesslick, W.J. Baldy, R.P. Shank, D.L. DiStefano, C.L. Fedde, and M.K. Scott Activity of aromatic substituted phenylpiperazines lacking affinity for dopamine binding sites in a preclinical test of antipsychotic efficacy J. Med. Chem. 32 5 1989 1052 1056 (Pubitemid 19122156)
13. S. Butini, S. Gemma, G. Campiani, S. Franceschini, F. Trotta, M. Borriello, N. Ceres, S. Ros, S.S. Coccone, M. Bernetti, M. De Angelis, M. Brindisi, V. Nacci, I. Fiorini, E. Novellino, A. Cagnotto, T. Mennini, K. Sandager-Nielsen, J.T. Andreasen, J. Scheel-Kruger, J.D. Mikkelsen, and C. Fattorusso Discovery of a new class of potential multifunctional atypical antipsychotic agents targeting dopamine D3 and serotonin 5-HT1A and 5-HT2A receptors: design, synthesis, and effects on behaviour J. Med. Chem. 52 1 2009 151 169
14. A. Deep, S. Jain, and P.C. Sharma Synthesis and anti-inflammatory activity of some novel biphenyl-4-carboxylic acid 5-(arylidene)-2-(aryl)-4- oxothiazolidin-3-yl amides Acta Pol. Pharm. 67 1 2010 63 67
15. R. Sharma, and P.S. Kodavanti In vitro effects of polychlorinated biphenyls and hydroxy metabolites on nitric oxide synthases in rat brain Toxicol. Appl. Pharmacol. 178 2002 127 136 (Pubitemid 34214661)
16. N. Sachan, S. Thareja, R. Agarwal, S.S. Kadam, and V.M. Kulkarni Substituted biphenyl ethanones as antidiabetic agents: synthesis and in-vivo screening Int. J. PharmTech Res. 1 4 2009 1625 1631
17. M.G. Setzu, G. Stefancich, P. LaColla, and S. Castellano Synthesis and antifungal properties of N-[(1,1′-biphenyl)-4-ylmethyl]-1H-imidazol-1- amine derivatives Farmaco 57 12 2002 1015 1018 (Pubitemid 35477631)
18. R.C. Dash, S.H. Bhosale, S.M. Shelke, M.R. Suryawanshi, A.M. Kanhed, and K.R. Mahadik Scaffold hopping for identification of novel D2 antagonist based on 3D pharmacophore modelling of illoperidone analogs Mol. Diversity 16 2 2012 367 375
19. N. Bodor, and P. Buchwald Recent advances in the brain targeting of neuropharmaceuticals by chemical delivery systems Adv. Drug. Delivery Rev. 36 1999 229 254 (Pubitemid 29121974)
20. Glide, Version 5.5 Schrödinger 2009 LLC New York, NY
21. S.R. Kesten, T.G. Heffner, S.J. Johnson, T.A. Pugsley, J.L. Wright, and L.D. Wise Design, synthesis, and evaluation of chromen-2-ones as potent and selective human dopamine D4 antagonists J. Med. Chem. 42 18 1999 3718 3725 (Pubitemid 29445105)
22. H.G. Vogel Drug Discovery and Evaluation: Pharmacological Assay 2002 Springer-Verlag Berlin Heidelberg New York
23. R.T. Khisti, S.N. Mandhane, and C.T. Chopde The neurosteroid 3 alpha-hydroxy-5 alpha-pregnan-20-one induces catalepsy in mice Neurosci. Lett. 251 2 1998 85 88 (Pubitemid 28358260)
24. MAESTRO, Version 9.0, Schrödinger 2009 LLC New York, NY
25. MacroModel, Version 9.7, Schrödinger 2009 LLC New York, NY
26. QikProp, Version 3.2, Schrödinger 2009 LLC New York, NY
27. Strike, Version 1.8, Schrödinger 2009 LLC New York, NY