Novel (bisarylmethoxy)butylpiperidine analogues as neurotransmitter transporter inhibitors with activity at dopamine receptor sites

Bioorganic and Medicinal Chemistry

Volumn 10, Issue 12, 2002, Pages 4091-4102

  Choi, Sung Woon ^a   Elmaleh, David R ^a   Hanson, Robert N ^b   Shoup, Timothy M ^a   Fischman, Alan J ^a  

^a MASSACHUSETTS GENERAL HOSPITAL   (United States)

^b NORTHEASTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 [1 [4 [BIS(4 FLUOROPHENYL)METHOXYL]BUTYL]PIPERIDIN 4 YL] 1,3 DIHYDROBENZOIMIDAZOL 2 ONE; 1 [4 [BIS(4 FLUOROPHENYL)METHOXY]BUTYL] 3 HYDROXYPIPERIDINE; 1 [4 [BIS(4 FLUOROPHENYL)METHOXY]BUTYL] 3 PIPERIDINE CARBOXAMIDE; 1 [4 [BIS(4 FLUOROPHENYL)METHOXY]BUTYL] 4 (4 BROMOPHENYL) 4 PIPERIDINOL; 1 [4 [BIS(4 FLUOROPHENYL)METHOXY]BUTYL] 4 ACETYL 4 PHENYLPIPERIDINE; 1 [4 [BIS(4 FLUOROPHENYL)METHOXY]BUTYL] 4 HYDROXYPIPERIDINE; 1 [4 [BIS(4 FLUOROPHENYL)METHOXY]BUTYL] 4 PHENYLPIPERIDIN 4 OL; 1 [4 [BIS(4 FLUOROPHENYL)METHOXY]BUTYL] 4 PHENYLPIPERIDINE 4 CARBONITRILE; 1 [4 [BIS(4 FLUOROPHENYL)METHOXY]ETHYL] 4 (4 BROMOPHENYL) 4 PIPERIDINOL; 2 [4 [4 (4 BROMOPHENYL) 4 HYDROXYPIPERIDIN 1 YL]BUTYL]ISOINDOLE 1,3 DIONE; 2 [4 [BIS(4 FLUOROPHENYL)METHOXY]BUTYL] 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 [4 [BIS(4 FLUOROPHENYL)METHOXY]BUTYL] 6,7 DIMETHOXY 1 PHENYL 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 [4 [BIS(4 FLUOROPHENYL)METHOXY]BUTYL] 6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE; 4 BENZYL 1 [4 [BIS(4 FLUOROPHENYL)METHOXY]BUTYL] 4 PIPERIDINOL; 8 [4 [BIS(4 FLUOROPHENYL)METHOXY]BUTYL] 1 PHENYL 1,3,8 TRIAZASPIRO[4,5]DECAN 4 ONE; COCAINE; DOPAMINE RECEPTOR; DOPAMINE TRANSPORTER; DOPAMINE UPTAKE INHIBITOR; NEUROTRANSMITTER; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ABSTINENCE; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; ATTENUATION; BINDING AFFINITY; COCAINE DEPENDENCE; CONTROLLED STUDY; DRUG ANTAGONISM; DRUG EFFECT; DRUG RECEPTOR BINDING; DRUG RESPONSE; DRUG SCREENING; DRUG SYNTHESIS; EMBRYO; HUMAN; HUMAN CELL; HYBRID; HYPERACTIVITY; IN VITRO STUDY; IN VIVO STUDY; LOCOMOTION; MALE; MOUSE; NEUROTRANSMISSION; NONHUMAN; PHARMACOPHORE; RAT; STIMULATION;

ANIMALS; CELL LINE; COCAINE; COCAINE-RELATED DISORDERS; DOPAMINE ANTAGONISTS; DOPAMINE PLASMA MEMBRANE TRANSPORT PROTEINS; HUMANS; HYPERKINESIS; LIGANDS; MALE; MEMBRANE GLYCOPROTEINS; MEMBRANE TRANSPORT PROTEINS; MICE; MOTOR ACTIVITY; NERVE TISSUE PROTEINS; NEUROTRANSMITTER UPTAKE INHIBITORS; PIPERIDINES; RADIOLIGAND ASSAY; RATS; RECEPTORS, DOPAMINE; RECEPTORS, SEROTONIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0036973278     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(02)00348-6     Document Type: Article

References (51)

1. (a) Das G. J. Clin. Pharmacol. 33:1993;296
2. (b) Substance Abuse and Mental Health Services Administration National Household Survey on Drug Abuse: Main Findings 1997; Department of Health and Human Services: Washington, D.C., 1998.
3. (c) McCance E.F. NIDA Res. Monogr. 175:1997;36.
4. For reviews, see (a) Carroll, F. I.; Lewin, A. H.; Boja, J. W.; Kuhar, M. J. J. Med. Chem. 1992 35 969, and references therein (b) Carroll F.I., Howell L.L., Kuhar M.J. J. Med. Chem. 42:1999;2721 (c) Howell L.L., Wilcox K.M. Prespectives in Pharmacology. 28:2001;1.
5. For reviews, see (a) Carroll, F. I.; Lewin, A. H.; Boja, J. W.; Kuhar, M. J. J. Med. Chem. 1992 35 969, and references therein (b) Carroll F.I., Howell L.L., Kuhar M.J. J. Med. Chem. 42:1999;2721 (c) Howell L.L., Wilcox K.M. Prespectives in Pharmacology. 28:2001;1.
6. For reviews, see (a) Carroll, F. I.; Lewin, A. H.; Boja, J. W.; Kuhar, M. J. J. Med. Chem. 1992 35 969, and references therein (b) Carroll F.I., Howell L.L., Kuhar M.J. J. Med. Chem. 42:1999;2721 (c) Howell L.L., Wilcox K.M. Prespectives in Pharmacology. 28:2001;1.
7. (a) Ritz M.C., Lamb R.J., Goldberg S.R., Kuhar M.J. Science. 237:1987;1219.
8. (b) Kuhar M.J., Ritz M.C., Boja J.W. Trends Neurosci. 14:1991;299.
9. (c) Giros B., Jaber M., Jones S.R., Wightman R.M., Caron M.G. Nature. 379:1996;606.
10. (a) Reith M.E.A., Sershen H., Lajtha A. Life Sci. 27:1980;1055.
11. (b) Reith M.E.A., Meisler B.E., Sershen H., Lajtha A. Brain Res. 342:1985;145.
12. (a) Witkin J.M. Neurosci. Biobehav. Rev. 18:1994;121.
13. (b) Mello N.K., Negus S.S. Neuropsychopharmacology. 14:1996;375.
14. (a) Spealman R.D. Psychopharmacology. 101:1990;142.
15. (b) Witkin J.M., Schindler C.W., Tella S.R., Goldberg S.R. Psychopharmacology. 104:1991;425.
16. (a) Corrigall W.A., Coen K.M. Pharmacol. Biochem. Behav. 39:1991;799.
17. (b) Britton D.R., Curzon P., MacKenzie R.G., Kebabian J.W., Williams J.E.G., Kerkman D. Pharmacol. Biochem. Behav. 39:1991;911.
18. Shafer R.A., Levant B. Psychopharmacology. 135:1998;1.
19. Pilla M., Perachon S., Sautel F., Garrido F., Mann A., Wermuth C.G., Schwartz J.-C., Everitt B.J., Sokoloff P. Nature. 400:1999;371.
20. Rothman R.B., Becketts K.M., Radesca L.R., de Costa B.R., Rice K.C., Carroll F.I., Dersch C.M. Life Sci. 53:1993;PL.
21. Deutsch H.M., Collard D.M., Zhang L., Burnham K.S., Deshpande A.K., Holtzman S.G., Schweri M.M. J. Med. Chem. 42:1999;882.
22. (a) Simoni D., Stoelwinder J., Kozikowski A.P., Johnson K.M., Bergmann J.S., Ball R.G. J. Med. Chem. 36:1993;3975.
23. (b) Nader M.A., Grant K.A., Davies H.M.L., Mach R.H., Childers S.R. J. Pharmacol. Exp. Ther. 280:1997;541.
24. (a) Matecka D., Rothman R.B., Radesca L., de Costa B.R., Dersch C.M., Partilla J.S., Pert A., Glowa J.R., Wojnicki F.H.E., Rice K.C. J. Med. Chem. 39:1996;4704.
25. (b) Matecka D., Lewis D., Rothman R.B., Dersch C.M., Wojnicki F.H.E., Glowa J.R., DeVries A.C., Pert A., Rice K.C. J. Med. Chem. 40:1997;705
26. (c) Zhang Y. Med. Chem. Res. 8:1998;66.
27. (a) Madras B.K., Reith M.E.A., Meltzer P.C., Dutta A.K. Eur. J. Pharmacol. 267:1994;167.
28. (b) Dutta A.K., Coffey L.L., Reith M.E.A. J. Med. Chem. 40:1997;35.
29. (a) van der Zee P., Koger H.S., Gootjes J., Hespe W. Eur. J. Med. Chem. 15:1980;363
30. (b) Rothman R.B., Mele A., Reid A.A., Akunne H.C., Greig N., Thurkauf A., de Costa B.R., Rice K.C., Pert A. Pharmacol. Biochem. Behav. 40:1991;387.
31. (c) Baumann M.H., Char G.U., de Costa B.R., Rice K.C., Rothman R.B. J. Pharmacol. Exp. Ther. 271:1994;1216
32. (d) Tella S.R., Ladenheim B., Andrews A.M., Goldberg S.R., Cadet J.L. J. Neurosci. 16:1996;7416.
33. Lewis D.B., Matecka D., Zhang Y., Hsin L.-W., Dersch C.M., Stafford D., Glowa J.R., Rothman R.B., Rice K.C. J. Med. Chem. 42:1999;5029.
34. Bergman J., Madras B.K., Johnson S.E., Spealman R.D. J. Pharmacol. Exp. Ther. 251:1989;150.
35. Howell L.L., Byrd L.D. J. Pharmacol. Exp. Ther. 258:1991;178.
36. Katz J.L., Izenwasser S., Terry P. Psychopharmacology. 148:2000;90.
37. Howell L.L., Czoty P.W., Byrd L.D. Psychopharmacology. 131:1997;40.
38. Deutsch H.M., Schweri M.M. Life Sci. 55:1994;PL.
39. (a) Hanson R.N., Choi S.-W., Elmaleh D.R., Fischman A. J. Bioorg. Med. Chem. Lett. 7:1997;2559.
40. (b) Choi S.-W., Elmaleh D.R., Hanson R.N., Fischman A.J. J. Med. Chem. 42:1999;3647.
41. Dutta A.K., Meltzer P.C., Madras B.K. Med. Chem. Res. 3:1993;209.
42. Taverne T., Diouf O., Depreux P., Poupaert J.H., Lesieur D., Guardiola-Lemaitre B., Renard P., Rettori M-C., Caignard D-H., Pfeiffer B. J. Med. Chem. 41:1998;2010.
43. Caliendo G., Fiorino F., Grieco P., Perissutti E., Santagada V., Severino B., Bruni G., Romeo M.R. Bioorg. Med. Chem. 8:2000;533.
44. Results from an arylpiperazine series are currently under manuscript preparation.
45. Ahmad Y.E., Maillet P., Laurent E., Talab A., Teste J.F., Cedat M.J., Fiez-Vandal P.Y., Dokhan R., Ollivier R. Eur. J. Med. Chem. 32:1997;205.
46. Eshleman A.J., Carmolli M., Cumbay M., Martens C.R., Neve K.A., Janowsky A. J. Pharmacol. Exp. Ther. 289:1999;877.
47. (a) In vitro pharmacological assays for receptors by NIDA/MDD (NIDA contract NO1DA-7-8072, Contract title: 'Receptor Activity Testing for Medication Discovery'.
48. (b) Chio C.L., Lajiness M.E., Huff R.M. Mol. Pharmacol. 45:1994;51.
49. Dubinsky B., McGuire J.L., Niemegeers C.J.E., Janssen P.A.J., Weintraub H.S., McKenzie B.E. Psychopharmacology. 78:1982;1.
50. After testing compounds 18 and 23 which are also potent NE reuptake inhibitor, NIDA indicated that they are looking for ligands that posses a high DR value and a high selectivity but with a low NE reuptake inhibition. Also, compound 22 contained a partial structure of a strong dopamine D2 receptor antagonist, and thus, metabolism might generate a N-dealkylation product, which has freezing activities that can be correlated to the EPS of conventional antipsychotics.
51. Manzanedo C., Aguilar M.A., Miñarro J. Psychopharmacology. 143:1999;82.