Syntheses of novel diphenyl piperazine derivatives and their activities as inhibitors of dopamine uptake in the central nervous system

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 8, 2003, Pages 1621-1630

  Kimura, Makoto ^a   Masuda, Tomoko ^a   Yamada, Koji ^a   Mitani, Masaki ^a   Kubota, Nobuo ^a   Kawakatsu, Nobuyuki ^a   Kishii, Kenichi ^a   Inazu, Masato ^b   Kiuchi, Yuji ^c   Oguchi, Katsuji ^c   Namiki, Takayuki ^a  

^a POLA CHEMICAL INDUSTRIES INC   (Japan)

^b TOKYO MEDICAL UNIVERSITY   (Japan)

^c SHOWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 FLUOROPHENYL) 4 (4 TRIPHENYLMETHYL 1 PIPERAZINE) 1 BUTANONE; 1 [(4 FLUOROPHENYL) 4 OXOBUTYL] 4 [(2 HYDROXY 3 PHENYLAMINO)PROPYL]PIPERAZINE; 1 [2 (BENZHYDRYLOXY)ETHYL] 4 (3 PHENYLPROPYL)PIPERAZINE; 1 [2 [BIS(4 FLUOROPHENYL)METHOXY]ETHYL 4 [2 HYDROXY 3 (PHENYLAMINO)PROPYL]PIPERAZINE DIMALEATE; 1 [2 [BIS(4 FLUOROPHENYL)METHOXY]ETHYL] 4 [2 HYDROXY 3 (PHENYLAMINO)PROPYL]PIPERAZINE; 1 [2 [BIS(4 FLUOROPHENYL)METHOXY]ETHYL] 4 [3 [(N ETHOXYCARBONYL N PHENYL)AMINO] 2 HYDROXYPROPYL]PIPERAZINE; 1 [2,2 BIS(4 FLUOROPHENYL)ETHYL] 4 [2 HYDROXY 3 (PHENYLAMINO)PROPYL]PIPERAZINE; 1 [2,2 BIS(4 FLUOROPHENYL)ETHYL] 4 [3 [(N ETHOXYCARBONYL N PHENYL)AMINO] 2 HYDROXYPROPYL]PIPERAZINE; 1 [3 [(N ETHOXYCARBONYL N PHENYL)AMINO] 2 HYDROXYPROPYL] 4 [(4 FLUOROPHENYL) 4 OXOBUTYL] 4 PIPERAZINE; 1 [3 [N,N BIS(4 FLUOROPHENYL)AMINO]PROPYL] 4 [2 HYDROXY 3 (PHENYLAMINO)PROPYL]PIPERAZINE; 1 [3 [N,N BIS(4 FLUOROPHENYL)AMINO]PROPYL] 4 [3 [(N ETHOXYCARBONYL N PHENYL)AMINO] 2 HYDROXYPROPYL]PIPERAZINE; 1 [3,3 BIS(4 FLUOROPHENYL)PROPYL] 4 [2 HYDROXY 3 (PHENYLAMINO)PROPYL]PIPERAZINE; 1 [3,3 BIS(4 FLUOROPHENYL)PROPYL] 4 [3 [(N ETHOXYCARBONYL N PHENYL)AMINO] 2 HYDROXYPROPYL]PIPERAZINE; 1 [4,4 BIS(4 FLUOROPHENYL) 3 BUTENYL] 4 [2 HYDROXY 3 (PHENYLAMINO)PROPYL]PIPERAZINE; 1 [4,4 BIS(4 FLUOROPHENYL) 3 BUTENYL] 4 [3 [(N ETHOXYCARBONYL N PHENYL)AMINO] 2 HYDROXYPROPYL]PIPERAZINE; 1 [4,4 BIS(4 FLUOROPHENYL) 4 HYDROXYBUTYL] 4 [2 HYDROXY 3 (PHENYLAMINO)PROPYL]PIPERAZINE; 1 [4,4 BIS(4 FLUOROPHENYL)BUTYL] 4 [2 HYDROXY 3 (PHENYLAMINO)PROPYL]PIPERAZINE; 1 [4,4 BIS(4 FLUOROPHENYL)BUTYL] 4 [3 [(N ETHOXYCARBONYL N PHENYL)AMINO] 2 HYDROXYPROPYL]PIPERAZINE; 1 [5,5 BIS(4 FLUOROPHENYL)PENTYL] 4 [2 HYDROXY 3 (PHENYLAMINO)PROPYL]PIPERAZINE; 1 [5,5 BIS(4 FLUOROPHENYL)PENTYL] 4 [3 [N ETHOXYCARBONYL N PHENYL)AMINO] 2 HYDROXYPROPYL]PIPERAZINE; 1 [BIS(4 FLUOROPHENYL)METHYL] 4 [2 HYDROXY 3 (PHENYLAMINO)PROPYL]PIPERAZINE; 1 [BIS(4 FLUOROPHENYL)METHYL] 4 [3 [(N ETHOXYCARBONYL N PHENYL)AMINO] 2 HYDROXYPROPYL]PIPERAZINE; 5 [4 [BIS(4 FLUOROPHENYL)METHYL] 1 PIPERAZINYL]METHYL 3 PHENYL 2 OXAZOLIDONE; DOPAMINE TRANSPORTER; DOPAMINE UPTAKE INHIBITOR; N (2,3 EPOXYPROPYL) N ETHOXYCARBONYLANILINE; PIPERAZINE DERIVATIVE; TRITIUM; UNCLASSIFIED DRUG; VANOXERINE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CENTRAL NERVOUS SYSTEM; CONTROLLED STUDY; DOPAMINE BRAIN LEVEL; DOPAMINE UPTAKE; DRUG ACTIVITY; DRUG INHIBITION; DRUG MECHANISM; DRUG SYNTHESIS; IC 50; MALE; MICRODIALYSIS; NONHUMAN; RAT; STRIATE CORTEX;

EID: 12244283141     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00061-0     Document Type: Article

References (44)

1. Kuhar M.J. Life Sci. 13:1973;1623.
2. Bernheimer H., Birkmayer W., Hornykiewicz O., Jellinger K., Seitelberger F. J. Neurol. Sci. 20:1973;415.
3. Brown A.S., Gershon S. J. Neural. Transm. Gen. Sect. 91:1993;75.
4. Carroll F.I., Howell L.L., Kuhar M.J. J. Med. Chem. 42:1999;2721.
5. Rothman R.B. Life Sci. 46:1990;17.
6. Graybiel A.M., Hirsch E.C., Agid Y. Adv. Neurol. 53:1990;17.
7. Nomoto M., Iwata S., Kaseda S. Folia Pharmacol. Jpn. 117:2001;111.
8. Sit S.Y. Curr. Pharm. Des. 6:2000;1211.
9. Le W.D., Jankovic J. Drugs Aging. 18:2001;389.
10. Nomoto M., Jpn J. Psychopharmacol. 16:1996;113.
11. Wang Y.X., Castagnoli N. Jr. J. Med. Chem. 38:1995;1904.
12. Lebreton L., Curet O., Gueddari S., Mazouz F., Bernard S., Burstein C., Milcent R. J. Med. Chem. 38:1995;4786.
13. Moron J.A., Campillo M., Perez V., Unzeta M., Pardo L. J. Med. Chem. 43:2000;1684.
14. Bäckström R., Honkanen E., Pippuri A., Kairisalo P., Pystynen J., Heinola K., Nissinen E., Linden I.B., Männistö P.T., Kaakkola S., Pohto P. J. Med. Chem. 32:1989;841.
15. Heikkila R.E., Manzino L. Eur. J. Pharmacol. 103:1984;241.
16. Pileblad E., Carlsson A. Neuropharmacology. 24:1985;689.
17. Ritz M.C., Lamb R.J., Goldberg S.R., Kuhar M.J. Science. 237:1987;1219.
18. Itoh K., Ikarashi Y., Way E.L., Maruyama Y. Neurosci. Lett. 125:1991;22.
19. Milius R.A., Saha J.K., Madras B.K., Neumeyer J.L. J. Med. Chem. 34:1991;1728.
20. Van der Zee P., Koger H.S., Goojtes J., Hespe W. Eur. J. Med. Chem. 15:1980;363.
21. Wang S., Sakamuri S., Enyedy I.J., Kozikowski A.P., Deschaux O., Bandyopadhyay B.C., Tella S.R., Zaman W.A., Johnson K.M. J. Med. Chem. 43:2000;351.
22. Wang S., Sakamuri S., Enyedy I.J., Kozikowski A.P., Zaman W.A., Johnson K.M. Bioorg. Med. Chem. 9:2001;1753.
23. Carroll F.I., Abraham P., Lewin A.H., Parham K.A., Boja J.W., Kuhar M.J. J. Med. Chem. 35:1992;2497.
24. Carroll F.I., Kotian P., Dehghani A., Gray J.L., Kuzemko M.A., Parham K.A., Abraham P., Lewin A.H., Boja J.W., Kuhar M.J. J. Med. Chem. 38:1995;379.
25. Carroll F.I., Lewin A.H., Boja J.W., Kuhar M.J. J. Med. Chem. 35:1992;969.
26. Dutta A.K., Meltzer P.C., Madras B.K. Med. Chem. Res. 3:1993;209.
27. 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.
28. Choi S.W., Elmaleh D.R., Hanson R.N., Fischman A.J. J. Med. Chem. 42:1999;3647.
29. Bogeso K.P. J. Med. Chem. 26:1983;935.
30. Dutta A.K., Xu C., Reith M.E.A. J. Med. Chem. 41:1998;3293.
31. Husbands S.M., Izenwasser S., Kopajtic T., Bowen W.D., Vilner B.J., Katz J.L., Newman A.H. J. Med. Chem. 42:1999;4446.
32. Dutta A.K., Xu C., Reith M.E.A. J. Med. Chem. 39:1996;749.
33. 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.
34. Dutta A.K., Coffey L.L., Reith M.E.A. J. Med. Chem. 40:1997;35.
35. Dutta A.K., Coffey L.L., Reith M.E.A. J. Med. Chem. 41:1998;699.
36. Kimura M., Masuda T., Yamada K., Kubota N., Kawakatsu N., Mitani M., Kishii K., Inazu M., Namiki T. Bioorg. Med. Chem. Lett. 12:2002;1947.
37. Kelley A.E., Lang C.G. Eur. J. Pharmacol. 167:1989;385.
38. Nakachi N., Kiuchi Y., Inagaki M., Inazu M., Yamazaki Y., Oguchi K. Eur. J. Pharmacol. 281:1995;195.
39. Gubert S., Braso M.A., Sacristan A., Ortiz J.A. Arzneim.-Forsch./Drug Res. 37:1987;1103.
40. Wolfgang, R.; Hansjorg, U.; Wilhelm, B.; Joachim, K. DE Patent 36 00 390, 1966.
41. Rajsner M., Kopicova Z., Holubek J., Svatek E., Metys J., Bartosova M., Miksik F., Protiva M. Collection Czechoslov. Chem. Commun. 43:1978;1760.
42. Bartl V., Dlabac A., Protiva M. Collection Czechoslov. Chem. Commun. 45:1980;3182.
43. Sindelar K., Rajsner M., Cervena I., Valenta V., Jilek J.O., Kakac B., Holubek J., Svatek E., Miksik F., Protiva M. Collection Czechoslov. Chem. Commun. 38:1973;3879.
44. Wise L.D., Pattison I.C., Butler D.E., DeWald H.A., Lewis E.P., Lobbestael S.J., Nordin I.C., Poschel B.P., Coughenour L.L. J. Med. Chem. 28:1985;606.