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

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 15, 2008, Pages 7291-7301

  Ablordeppey, Seth Y ^a   Altundas, Ramazan ^a   Bricker, Barbara ^a   Zhu, Xue Y ^a   Suresh Kumar, Eyunni V K ^a   Jackson, Tanise ^a   Khan, Abdul ^a   Roth, Bryan L ^b  

^a FLORIDA A AND M UNIVERSITY   (United States)

^b UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

Author keywords

Antipsychotics; Atypical antipsychotics; Butyrophenone; D2 like receptor ligands; Diazepane; Dopamine receptor ligands; Haloperidol; Serotonin receptor ligands

Indexed keywords

4 [3 (4 CHLOROPHENYL) 3,9 DIAZABICYCLO[4.2.1]NON 9 YL] 1 (4 FLUOROPHENYL)BUTAN 1 ONE; 4 [4 (2 PYRIMIDINE)PIPERAZIN 1 YL] 1 (4 FLUOROPHENYL)BUTAN 1 ONE; 4 [4 (4 CHLOROPHENYL) 1,4 DIAZEPAN 1 YL] 1 (FLUOROPHENYL)BUTAN 1 ONE; 4 [5 (4 CHLOROPHENYL) 2,5 DIAZABICYCLO[2.2.1]HEPT 2 YL] 1 (4 FLUOROPHENYL)BUTAN 1 ONE; 8 PHENYL 3,8 DIAZABICYCLO[3.2.1]OCTAN 1 YL 1 (4 FLUOROPHENYL)BUTAN 1 ONE; ARIPIPRAZOLE; BUTYROPHENONE DERIVATIVE; CLOZAPINE; DOPAMINE TRANSPORTER; HALOPERIDOL; NEUROLEPTIC AGENT; NORADRENALIN TRANSPORTER; OLANZAPINE; QUETIAPINE; RECEPTOR SUBTYPE; RISPERIDONE; SEROTONIN 1A RECEPTOR; SEROTONIN 2A RECEPTOR; SEROTONIN 2C RECEPTOR; SEROTONIN RECEPTOR; UNCLASSIFIED DRUG; ZIPRASIDONE;

ANIMAL EXPERIMENT; ARTICLE; BINDING AFFINITY; CATALEPSY; CONTROLLED STUDY; DRUG DOSE INCREASE; DRUG EFFICACY; DRUG IDENTIFICATION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SYNTHESIS; EXPERIMENTAL MODEL; EXPERIMENTAL MOUSE; EXPERIMENTAL RAT; IN VIVO STUDY; MALE; MOUSE; NONHUMAN; RAT;

ANIMALS; ANTIPSYCHOTIC AGENTS; APOMORPHINE; AZEPINES; BUTYROPHENONES; CLOZAPINE; HALOPERIDOL; LETHAL DOSE 50; MALE; MICE; MOLECULAR STRUCTURE; RATS; RATS, SPRAGUE-DAWLEY; STEREOTYPED BEHAVIOR; STRUCTURE-ACTIVITY RELATIONSHIP;

RATTUS;

EID: 48449091717     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.06.030     Document Type: Article

References (56)

1. Crilly J. Hist. Psychiatry 18 (2007) 39
2. Peabody C.A., Brody D., and Warner M.D. Biol. Psychiatry 22 (1987) 111
3. Riddle M.A., Hardin M.T., Towbin K.E., Leckman J.F., and Cohen D.J. Arch. Gen. Psychiatry 44 (1987) 98
4. Chirita V., Boisteanu P., and Pirozynski T. Rev. Med. Chir. Soc. Med. Nat. Iasi. 91 (1987) 53
5. Munyon W.H., Salo R., and Briones D.F. Psychopharmacology (Berlin) 91 (1987) 182
6. Petty L.K., and Spar C.J. Am. J. Psychiatry 137 (1980) 745
7. Gerlach J., and Simmelsgaard H. Psychopharmacology (Berlin) 59 (1978) 105
8. Ablordeppey S.Y., and Borne R.F. Pharmacol. Biochem. Behav. 46 (1993) 739
9. Subramanyam B., Rollema H., Woolf T., and Castagnoli Jr. N. Biochem. Biophys. Res. Commun. 166 (1990) 238
10. Subramanyam B., Pond S.M., Eyles D.W., Whiteford H.A., Fouda H.G., and Castagnoli Jr. N. Biochem. Biophys. Res. Commun. 181 (1991) 573
11. Subramanyam B., Woolf T., and Castagnoli Jr. N. Chem. Res. Toxicol. 4 (1991) 123
12. Fang J., and Gorrod J.W. Toxicol. Lett. 59 (1991) 117
13. Eyles D.W., McLennan H.R., Jones A., McGrath J.J., Stedman T.J., and Pond S.M. Clin. Pharmacol. Ther. 56 (1994) 512
14. Eyles D.W., Avent K.M., Stedman T.J., and Pond S.M. Life Sci. 60 (1997) 529
15. Fang J., Zuo D., and Yu P.H. Psychopharmacology 121 (1995) 373
16. Rollema H., Skolnik M., D'Engelbronner J., Igarashi K., Usuki E., and Castagnoli Jr. N. J. Pharmacol. Exp. Ther. 268 (1994) 380
17. Ablordeppey S.Y., Lyles-Eggleston M., Bricker B., Zhang W., Zhu X.Y., Goodman C., and Roth B.L. Bioorg. Med. Chem. Lett. 16 (2006) 3219
18. Ablordeppey S.Y., and Borne R.F. Med. Chem. Res. 3 (1993) 459
19. Lyles-Eggleston M., Altundas R., Xia J., Sikazwe D.M.N., Fan P., Yang Q., Li S., Zhang W., Zhu X., Schmidt A.W., Vanase-Frawley M., Shrihkande A., Villalobos A., and Ablordeppey S.Y. J. Med. Chem. 47 (2004) 497
20. Sikazwe D.M.N., Li S., Mardenborough L., Cody V., Roth B.L., and Ablordeppey S.Y. Bioorg. Med. Chem. Lett. 14 (2004) 5739
21. Sikazwe D.M.N., Li S., Lyles-Eggleston M., and Ablordeppey S.Y. Bioorg. Med. Chem. Lett. 13 (2003) 3779
22. Tacke R., Popp F., Müller B., Theis B., Burschka C., Hamacher A., Kassack M.U., Schepmann D., Wünsch B., Jurva U., and Wellner E. ChemMedChem 3 (2008) 152
23. McIntyre R.S., McCann S.M., and Kennedy S.H. Can. J. Psychiatry 46 (2001) 273
24. Taylor D.M., and McAskill R. Acta Psychiatry Scand. 101 (2000) 416
25. Wirshing D.A., Spellberg B.J., Erhart S.M., Marder S.R., and Wirshing W.C. Biol. Psychiatry 44 (1998) 778
26. Seeger T.F., Seymour P.A., Schmidt A.W., Zorn S.H., Schulz D.W., Lebel L.A., McLean S., Guanowsky V., Howard H.R., Lowe J.A., and Heym J. J. Pharmacol. Exp. Ther. 275 (1995) 101
27. Schmidt A.W., Lebel L.A., Howard Jr. H.R., and Zorn S.H. Eur. J. Pharmacol. 425 (2001) 197
28. McCreary A.C., Glennon J.C., Ashby Jr. C.R., Meltzer H.Y., Li Z., Reinders J.H., Hesselink M.B., Long S.K., Herremans A.H., van Stuivenberg H., Feenstra R.W., and Kruse C.G. Neuropsychopharmacology 32 (2007) 78
29. Matsui-Sakata A., Ohtani H., and Sawada Y. Drug Metab. Pharmacokinet. 20 (2005) 368
30. Sanberg P.R., Bunsey M.D., Giordano M., and Norman A.B. Behav. Neurosci. 102 (1988) 748
31. Crocker A.D., and Hemsley K.M. Prog. Neuropsychophamachol. Biol. Psychiatry 25 (2001) 573
32. Hoffman D.C., and Donovan H. Psychopharmacology 120 (1995) 128
33. Cignarella G., Giangiacomo N., and Emilio O. J. Org. Chem. 26 (1961) 2747
34. Thompson P.E., Zeigler J.B., and McCall J.W. J. Med. Chem. 17 (1974) 481
35. Yevich J.P., New J.S., Lobeck W.G., Dextraze P., Bernstein E., Taylor D.P., Yocca F.D., Eison M.S., and Temple Jr. D.L. J. Med. Chem. 35 (1992) 4516
36. Seeman P., Lee T., Chau-Wong M., and Wong K. Nature 261 (1976) 717
37. Seeman P., Chau-Wong M., Tedesco J., and Wong K. Proc. Natl. Acad. Sci. U.S.A. 72 (1975) 4376
38. Seeman P., Corbett R., and Van Tol H.H.M. Neuropsychopharmacology 16 (1997) 93
39. Bardin L., Auclair A., Kleven M.S., Prinssen E.P., Koek W., Newman-Tancredi A., and Depoortère R. Behav. Pharmacol. 18 (2007) 103
40. Cuisiat S., Bourdiol N., Lacharme V., Newman-Tancredi A., Colpaert F., and Vacher B. J. Med. Chem. 50 (2007) 865
41. Meltzer H.Y., Matsubara S., and Lee J.-C. J. Pharmacol. Exp. Ther. 251 (1989) 238
42. Rasmussen K., and Aghajanian G.K. Neuropsychopharmacology 1 (1988) 101
43. Meltzer H.Y., Li Z., Kaneda Y., and Ichikawa J. Prog. Neuropsychopharmacol. Biol. Psychiatry 27 (2003) 1159
44. Kroeze W.K., Hufeisen S.J., Popadak B.A., Renock S.M., Steinberg S., Ernsberger P., Jayathilake K., Meltzer H.Y., and Roth B.L. Neuropsychopharmacology 28 (2003) 519
45. Matsui-Sakata A., Ohtani H., and Sawada Y. Drug Metab. Pharmacokinet. 20 (2005) 368
46. Setola V., Dukat M., Glennon R.A., and Roth B.L. Mol. Pharmacol. 68 (2005) 20
47. Rothman R.B., Baumann M.H., Savage J.E., Rauser L., McBride A., Hufeisen S.J., and Roth B.L. Circulation 102 (2000) 2836
48. http://cardiology.jwatch.org/cgi/content/full/2007/103/2.
49. http://www.rxlist.com/cgi/generic/abilify_cp.htm.
50. Michaels R.J., and Zaugg H.E. J. Org. Chem. 25 (1960) 637
51. Shapiro D.A., Renock S., Arrington E., Chiodo L.A., Liu L.X., Sibley D.R., Roth B.L., and Mailman R. Neuropsychopharmacology 28 (2003) 1400
52. See references in Ref. 25.
53. Needham P.L., Atkinson J., Skill M.J., and Heal D.J. Psychopharmacol. Bull. 32 (1996) 123
54. Protais P., Costentin J., and Schwartz J.C. Psychopharmacology 50 (1976) 1
55. Hoffman D.C., and Donovan H. Psychopharmacology (Berlin) 120 (1995) 128
56. Hoffman D.C., and Donovan H. Psychopharmacology (Berlin) 115 (1994) 447