Synthesis and evaluation of a series of 2-substituted-5-thiopropylpiperazine (piperidine)-1,3,4-oxadiazoles derivatives as atypical antipsychotics

PLoS ONE

Volumn 7, Issue 4, 2012, Pages

  Chen, Yin ^a   Xu, Xiangqing ^b   Liu, Xin ^a   Yu, Minquan ^b   Liu, Bi Feng ^a   Zhang, Guisen ^a,b  

^a HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b Jiangsu Nhwa Pharmaceutical Co Ltd   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 [3 [4 (6 FLUOROBENZO[D]ISOXAZOL 3 YL)PIPERIDIN 1 YL]PROPYLTHIO] 5 (4 CHLOROPHENYL) 1,3,4 OXADIAZOLE; 2 [3 [4 (6 FLUOROBENZO[D]ISOXAZOL 3 YL)PIPERIDIN 1 YL]PROPYLTHIO] 5 (4 FLUOROPHENYL) 1,3,4 OXADIAZOLE; 2 [3 [4 (6 FLUOROBENZO[D]ISOXAZOL 3 YL)PIPERIDIN 1 YL]PROPYLTHIO] 5 (4 METHOXYPHENYL) 1,3,4 OXADIAZOLE; 2 [3 [4 (6 FLUOROBENZO[D]ISOXAZOL 3 YL)PIPERIDIN 1 YL]PROPYLTHIO] 5 (NAPHTHALEN 1 YL) 1,3,4 OXADIAZOLE; 2 [3 [4 (6 FLUOROBENZO[D]ISOXAZOL 3 YL)PIPERIDIN 1 YL]PROPYLTHIO] 5 [4 (TRIFLUOROMETHYL)PHENYL] 1,3,4 OXADIAZOLE; 2 [3 [4 (6 FLUOROBENZO[D]ISOXAZOL 3 YL)PIPERIDIN 1 YL]PROPYLTHIO] 5 PHENYL 1,3,4 OXADIAZOLE; 2 [3 [4 (BENZO[D]ISOTHIAZOL 3 YL)PIPERAZIN 1 YL]PROPYLTHIO] 5 (4 FLUOROPHENYL) 1,3,4 OXADIAZOLE; 2 [3 [4 (BENZO[D]ISOTHIAZOL 3 YL)PIPERAZIN 1 YL]PROPYLTHIO] 5 (NAPHTHALEN 1 YL) 1,3,4 OXADIAZOLE; 2 [3 [4 (BENZO[D]ISOTHIAZOL 3 YL)PIPERAZIN 1 YL]PROPYLTHIO] 5 (THIOPHEN 1 YL) 1,3,4 OXADIAZOLE; 2 [[3 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]PROPYL]THIO] 5 PHENYL 1,3,4 OXADIAZOLE; 2 [[3 [4 (2,3 DICHLOROPHENYL)PIPERAZIN 1 YL]PROPYL]THIO] 5 PHENYL 1,3,4 OXADIAZOLE; 2 [[3 [4 (2,3 DIMETHYLPHENYL)PIPERAZIN 1 YL]PROPYL]THIO] 5 PHENYL 1,3,4 OXADIAZOLE; 2 [[3 [4 (BENZO[D]ISOTHIAZOL 3 YL)PIPERAZIN 1 YL]PROPYL]THIO] 5 (4 CHLOROPHENYL) 1,3,4 OXADIAZOLE; 2 [[3 [4 (BENZO[D]ISOTHIAZOL 3 YL)PIPERAZIN 1 YL]PROPYL]THIO] 5 (4 METHOXYPHENYL) 1,3,4 OXADIAZOLE; 2 [[3 [4 (BENZO[D]ISOTHIAZOL 3 YL)PIPERAZIN 1 YL]PROPYL]THIO] 5 PHENYL 1,3,4 OXADIAZOLE; 2 [[3 [4 (BENZO[D]ISOXAZOL 3 YL)PIPERAZIN 1 YL]PROPYL]THIO] 5 [4 (TRIFLUOROMETHYL)PHENYL] 1,3,4 OXADIAZOLE; 2 [[3 [4 [3 (TRIFLUOROMETHYL)PHENYL]PIPERAZIN 1 YL]PROPYL]THIO] 5 PHENYL 1,3,4 OXADIAZOLE; 2 SUBSTITUTED 5 THIOPROPYLPIPERAZINE 1,3,4 OXADIAZOLE DERIVATIVE; APOMORPHINE; ATYPICAL ANTIPSYCHOTIC AGENT; CLOZAPINE; DOPAMINE 2 RECEPTOR; DOPAMINE 3 RECEPTOR; HALOPERIDOL; HISTAMINE H1 RECEPTOR; RISPERIDONE; SEROTONIN 1A RECEPTOR; SEROTONIN 2A RECEPTOR; SEROTONIN 2C RECEPTOR; UNCLASSIFIED DRUG; UNINDEXED DRUG; NEUROLEPTIC AGENT; OXADIAZOLE DERIVATIVE; PIPERIDINE DERIVATIVE; SEROTONIN 1 RECEPTOR;

ACUTE TOXICITY; ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; BINDING AFFINITY; CATALEPSY; CLIMBING; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG DOSE INCREASE; DRUG HALF LIFE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; EXTRAPYRAMIDAL SYMPTOM; FEMALE; HYPERACTIVITY; LD 50; MALE; MAXIMUM PLASMA CONCENTRATION; MOUSE; NONHUMAN; RAT; TIME TO MAXIMUM PLASMA CONCENTRATION; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DEVELOPMENT; HUMAN; HYPERKINESIA; METABOLISM; METHODOLOGY; PROTEIN BINDING; SCHIZOPHRENIA; SYNTHESIS;

MUS;

ANIMALS; ANTIPSYCHOTIC AGENTS; DRUG DISCOVERY; HUMANS; HYPERKINESIS; MICE; MOLECULAR STRUCTURE; OXADIAZOLES; PIPERIDINES; PROTEIN BINDING; RECEPTORS, DOPAMINE D2; RECEPTORS, DOPAMINE D3; RECEPTORS, SEROTONIN, 5-HT1; SCHIZOPHRENIA;

EID: 84860447812     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0035186     Document Type: Article

References (51)

1. Lewine RRJ, Fogg L, Meltzer HY, (1983) Assessment of Negative and Positive Symptoms in Schizophrenia. Schizophr Bull 9: 368-376.
2. Marde SR, Wirshing WC, Van Putten T, (1991) Drug treatment of schizophrenia. Overview of recent research. Schizophr Res 4: 81-90.
3. Baldessarini RJ, Tarsy D, (1980) Dopamine and the pathophysiology of dyskinesias induced by antipsychotic drugs. Annu Rev Neurosci 3: 23-41.
4. Boyd AE, Reichlin S, (1978) Neural control of prolactin secretion in man. Psychoneuroendocrino 3: 113-130.
5. Campbell M, Young PI, Bateman DN, (1999) The use of atypical antipsychotics in the management of schizophrenia. Br J Clin Pharmacol 47: 13-22.
6. Jones CA, McCreary AC, (2008) Serotonergic approaches in the development of novel antipsychotics. Neuropharmacology 55: 1056-1063.
7. Shapiro D, Renock S, Arrington E, Chiodo L, Liu L, et al. (2003) Aripiprazole: a novel atypical antipsychotic drug with a unique and robust pharmacology. Neuropsychopharmacol 28: 1400-1411.
8. Roth BL, Hanizavareh SM, Blum AE, (2004) Serotonin receptors represent highly favorable molecular targets for cognitive enhancement in schizophrenia and other disorders. Psychopharmacology 174: 17-24.
9. Meltzer HY, Li Z, Kaneda Y, Ichikawa J, (2003) Serotonin receptors: their key role in drugs to treat schizophrenia. Prog Neuropsychopharmacol Biol Psych 27: 1159-1172.
10. Butini S, Gemma S, Campiani G, Franceschini S, Trotta F, et al. (2009) 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 behavior. J Med Chem 52: 151-169.
11. Tamminga CA, (1997) The promise of new drugs for schizophrenia treatment. Can J Psychiatry 42: 265-273.
12. Vohora D, (2007) Atypical antipsychotic drugs: current issues of safety and efficacy in the management of schizophrenia. Curr Opin Invest Drugs 8: 531-538.
13. Schultz SH, North SW, Shields CG, (2007) Schizophrenia: a review. Am Fam Physician 75: 1821-1829.
14. Meltzer HY, (2004) What's atypical about atypical antipsychotic drugs? Curr Op Pharmacol 4: 53-57.
15. Morphy R, Rankovic Z, (2009) Designing Multiple Ligands - Medicinal Chemistry Strategies and Challenges. Curr Pharm Des 15: 587-600.
16. Wong EH, Tarazi FI, Shahid M, (2010) The effectiveness of multi-target agents in schizophrenia and mood disorders: Relevance of receptor signature to clinical action. Pharmacol Ther 126: 173-185.
17. Ohno Y, (2010) New insight into the therapeutic role of 5-HT1A receptors in central nervous system disorders. Cent Nerv Syst Agents Med Chem 10: 148-157.
18. Politis M, Wu K, Loane C, Quinn NP, Brooks DJ, et al. (2010) Serotonergic neurons mediate dyskinesia side effects in Parkinson's patients with neural transplants. Sci Transl Med 2: 38-46.
19. Millan MJ, (2000) Improving the Treatment of Schizophrenia: Focus on Serotonin (5-HT)1A Receptors. J Pharmacol Exp Ther 295: 853-861.
20. Meltzer HY, Matsubara S, Lee MA, (1989) Classification of typical and atypical antipsychotic drug on the basis of D1, D2 and serotonin 2 pK values. J Pharmacol Exp Ther 251: 238-246.
21. Meltzer HY, (2004) Cognitive factors in schizophrenia: causes, impact, and treatment. CNS Spectrosc 9: 15-24.
22. Bézard E, Ferry S, Mach U, Stark H, Leriche L, (2003) Attenuation of Levodopa-Induced Dyskinesia by Normalizing Dopamine D(3) Receptor Function. Nat Med 9: 762-767.
23. Millan MJ, Loiseau F, Dekeyne A, Gobert A, Flik G, et al. (2008) S33138 (N-[4-[2-[(3aS,9bR)-8-cyano-1,3a,4,9b-tetrahydro[1] benzopyrano[3,4-c]pyrrol-2(3H)-yl)-ethyl]phenyl-acetamide), a Preferential Dopamine D3 versus D2 Receptor Antagonist and Potential Antipsychotic Agent: III. Actions in Models of Therapeutic Activity and Induction of Side Effects. J Pharmacol Exper Ther 324: 1212-1226.
24. Kroeze WK, Hufeisen SJ, Popadak BA, Renock S, Steinberg S, et al. (2003) H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs. Neuropsychopharmacol 28: 519-526.
25. Kim SF, Huang AS, Snowman AD, Teuscher T, Snyder SH, (2007) Antipsychotic Drug-Induced Weight Gain Mediated by Histamine H1 Receptor-Linked Activation of Hypothalamic AMP-Kinase. Proc Natl Acad Sci USA 104: 3456-3459.
26. Reavill C, Kettle A, Holland V, Riley G, Blackburn TP, (1999): Attenuation of haloperidol-induced catalepsy by a 5-HT2C receptor antagonist. Br J Pharmacol 126: 572-574.
27. Wood MD, Reavill C, Trail B, Wilson A, Stean T, et al. (2001) SB-243213; a selective 5-HT2C receptor inverse agonist with improved anxiolytic profile: Lack of tolerance and withdrawal anxiety. Neuropharmacology 41: 186-199.
28. Buckland PR, Hoogendoorn B, Guy CA, Smith SK, Coleman SL, (2005) Low gene expression conferred by association of an allele of the 5-HT2C receptor gene with antipsychotic-induced weight gain. Am. J. Psychiatry 162: 613-615.
29. Reynolds GP, Hill MJ, Kirk SL, (2006) The 5-HT2C receptor and antipsychoticinduced weight gain-mechanisms and genetics. J Psychopharmacol 20: 15-18.
30. Garzya V, Forbes IT, Gribble AD, Hadley MS, Lightfoot AP, et al. (2007) Studies towards the identification of a new generation of atypical antipsychotic agents. Bioorg Med Chem Lett 17: 400-405.
31. Ablordeppey SY, Altundas R, Bricker B, Zhu XY, Kumar EV, et al. (2008) Identification of a butyrophenone analog as a potential atypical antipsychotic agent: 4-[4-(4-Chlorophenyl)-1,4-diazepan-1-yl]-1-(4-fluorophenyl)butan-1-one. Bioorg Med Chem 16: 7291-7301.
32. Neves G, Menegatti R, Antonio CB, Grazziottin LR, Vieira RO, et al. (2010) Searching for multi-target antipsychotics: Discovery of orally active heterocyclic N-phenylpiperazine ligands of D2-like and 5-HT1A receptors. Bioorg Med Chem 18: 1925-1935.
33. Glennon RA, Naiman RA, Lyon RA, Titeler M, (1988) Arylpiperazine Derivatives as High-Affinity 5-HT1A Serotonin Ligands. J Med Chem 31: 1968-1971.
34. Lowe JA, Seeger TF, Nagel AA, Howard HR, Seymour PA, et al. (1991) 1-Naphthylpiperazine derivatives as potential atypical antipsychotic agents. J Med Chem 34: 1860-1866.
35. Obniska J, Kolaczkowski M, Bojarski AJ, Duszyńska B, (2006) Synthesis, anticonvulsant activity and 5-HT1A, 5-HT2A receptor affinity of new N-[(4-arylpiperazin-1-yl)-alkyl] derivatives of 2-azaspiro[4.4]nonane and [4.5]decane-1,3-dione. Eur J Med Chem 41: 874-881.
36. Costall B, Naylor RJ, Nohria V, (1978) Climbing behaviour induced by apomorphine in mice: A potential model for the detection of neuroleptic activity. Eur J Pharmacol 50: 39-50.
37. Campiani G, Butini S, Fattorusso C, Catalanotti B, Gemma S, et al. (2004) Pyrrolo[1,3]benzothiazepine-based serotonin and dopamine receptor antagonists. Molecular modeling, further structure-activity relationship studies, and identification of novel atypical antipsychotic agents. J Med Chem 47: 143-157.
38. Xiberas X, Martinot JL, Mallet L, Artiges E, Loc'H C, et al. (2001) Extrastriatal and striatal D2 dopamine receptor blockade with haloperidol or new antipsychotic drugs in patients with schizophrenia. Br J Psychiatry 179: 503-508.
39. Gaonkar SL, Rai KML, Prabhuswamy B, (2006) Synthesis and antimicrobial studies of a new series of 2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}-5-substituted-1,3,4-oxadiazoles. Eur J Med Chem 41: 841-846.
40. Doria JS, Fanny PB, Marina I, Mesquita PKF, et al. (2011) Novel benzofuroxan derivatives against multidrug-resistant Staphylococcus aureus strains: Design using Topliss decision tree, synthesis and biological. Bioorg Med Chem 19: 5031-5038.
41. Li XR, Zhao ZG, Li GH, Shi PY, (2010) Design and synthesis of novel molecular tweezer anion receptors based on diphenic acid carbonyl thiosemicarbazide. J Chem Res (S) 7: 410-413.
42. Abdel-Aziz M, Abuo-Rahma GD, Hassan AA, (2009) Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities. Eur J Med Chem 44: 3480-3487.
43. Rao MEB, Rajurkar VG, (2011) Synthesis and biological studies of N-phenyl substituted 2-(5-(pyridin-4-yl)-1,3,4-oxadiazol-2-ylthio)acetamides. Asian J Chem 23: 2648-2652.
44. Liu F, Luo XQ, Song BA, Bhadury PS, Yang S, et al. (2008) Synthesis and antifungal activity of novel sulfoxide derivatives containing trimethoxyphenyl substituted 1, 3, 4-thiadiazole and 1, 3, 4-oxadiazole moiety. Bioorg Med Chem 16: 3632-3640.
45. Joshi S, Karnik AV, (2002) Facile conversion of acyldiithiocarbazinate salts to 1,3,4-oxadiazole derivatives under microwave irradiation. Synthetic Commun 32: 111-114.
46. Mission NAD, Doyle WC Jr, Kans L, (1969) Combating unwanted vegetation with 2-aryl-5- substituted 1,3,4-oxadiazoles.
47. Oreste T, Mario G, (1963) 2-Mercapto-5-heterocyclic-substituted-1,3,4-oxadiazoles. Annali di Chimica 53: 1687-1698.
48. Pramanik SS, Mukherjee A, (1998) Synthesis and in-vitro serotonin-3-antagonist activities of some new 1,3,4-oxadiazole-2-thiones. J Indian Chem Soc 75: 53-54.
49. Frecentese F, Fiorino F, Perissutti E, Severino B, Magli E, (2010) Efficient microwave combinatorial synthesis of novel indolic arylpiperazine derivatives as serotoninergic ligands. Eur J Med Chem 45: 752-759.
50. Dini S, Caselli GF, Ferrari MP, Giani R, Clavenna G, (1991) Heterogenity of [3H]-mepyramine binding sites in guinea pig cerebellum and lung. Agents Actions 33: 181-184.
51. Khisti RT, Mandhane SN, Chopde CT, (1998) The neurosteroid 3α-hydroxy-5α-pregan-20-one induces catalepsy in mice. Neurosci Lett 251: 85-88.