Novel potent neuropeptide Y Y5 receptor antagonists: Synthesis and structure-activity relationships of phenylpiperazine derivatives

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 22, 2006, Pages 7501-7511

  Takahashi, Toshiyuki ^a   Sakuraba, Aya ^a   Hirohashi, Tomoko ^a   Shibata, Takunobu ^a   Hirose, Masaaki ^a   Haga, Yuji ^a   Nonoshita, Katsumasa ^a   Kanno, Tetsuya ^a   Ito, Junko ^a   Iwaasa, Hisashi ^a   Kanatani, Akio ^a   Fukami, Takehiro ^a   Sato, Nagaaki ^a  

^a BANYU PHARMACEUTICAL CO LTD   (Japan)

Author keywords

(2 Methanesulfonamidephenyl)piperazine derivatives; Anti obesity; Neuropeptide Y Y5 receptor; Y5 antagonist

Indexed keywords

1 PHENYLPIPERAZINE DERIVATIVE; 4 (2 CHLOROPHENYL) N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL]PIPERAZINE 1 CARBOXAMIDE; 4 (3 CHLOROPHENYL) N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL]PIPERAZINE 1 CARBOXAMIDE; 4 (4 CHLOROPHENYL) N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL]PIPERAZINE 1 CARBOXAMIDE; 4 [2 [(METHYLSULFONYL)AMINO]PHENYL] N (3 PHENYL 1H PYRAZOL 5 YL)PIPERAZINE 1 CARBOXAMIDE; 4 BENZYL N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL]PIPERAZINE 1 CARBOXAMIDE; METHYL 2 [4 [[[3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL]AMINO]CARBONYL]PIPERAZIN 1 YL]BENZOATE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 1,3 DIHYDRO 2H ISOINDOLE 2 CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 3,4 DIHYDROISOQUINOLINE 2(1H) CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 4 (2 ACETYLAMINOPHENYL)PIPERAZINE 1 CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 4 (2 CYANOPHENYL)PIPERAZINE 1 CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 4 (2 METHOXYPHENYL)PIPERAZINE 1 CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 4 (2 METHYLPHENYL)PIPERAZINE 1 CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 4 (2 NITROPHENYL)PIPERAZINE 1 CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 4 (3 METHOXYPHENYL)PIPERAZINE 1 CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 4 (3 METHYLPHENYL)PIPERAZINE 1 CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 4 (4 METHOXYPHENYL)PIPERAZINE 1 CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 4 (4 METHYLPHENYL)PIPERAZINE 1 CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 4 [2 (DIMETHYLAMINO)PHENYL] PIPERAZINE 1 CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 4 [2 (METHYLAMINO)PHENYL]PIPERAZINE 1 CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 4 [2 (METHYLSULFONYL)PHENYL] PIPERAZINE 1 CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 4 [2 [(METHYLSULFONYL)AMINO]PHENYL] PIPERAZINE 1 CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 4 [2 [METHYL(METHYLSULFONYL)AMINO] PHENYL]PIPERAZINE 1 CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 4 [3 [(METHYLSULFONYL)AMINO]PHENYL] PIPERAZINE 1 CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 4 [4 [(METHYLSULFONYL)AMINO]PHENYL] PIPERAZINE 1 CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 4 PHENYLPIPERAZINE 1 CARBOXAMIDE; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] N' (2,3 DIHYDRO 1H INDEN 1 YL)UREA; N [3 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] N' (2,3 DIHYDRO 1H INDEN 2 YL)UREA; NEUROPEPTIDE Y RECEPTOR ANTAGONIST; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG BINDING; DRUG SCREENING; DRUG STRUCTURE; DRUG SUBSTITUTION; DRUG SYNTHESIS;

HUMANS; MOLECULAR STRUCTURE; PIPERAZINES; RECEPTORS, NEUROPEPTIDE Y; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33749250382     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.07.023     Document Type: Article

References (30)

1. Tatemoto K., Carlquist M., and Mutt V. Nature 296 (1982) 659
2. Clark J.T., Kalra P.S., Crowley W.R., and Kalra S.P. Endocrinology 115 (1984) 427
3. Stanley B.G., and Leibowitz S.F. Life Sci. 35 (1984) 2635
4. Stanley B.G., Kyrkouli S.E., Lampert S., and Leibowitz S.F. Peptides 7 (1986) 1189
5. Stanley B.G., Magdalin W., Seirafi A., Nguyen M.M., and Leibowitz S.F. Peptides 13 (1992) 581
6. Zarjevski N., Cusin I., Vettor R., Rohner-Jeanrenaud F., and Jeanrenaud B. Endocrinology 133 (1993) 1753
7. Kalra S.P., Dube M.G., Sahu A., Phelps C.P., and Kalra P.S. Proc. Natl. Acad. Sci. U.S.A. 88 (1991) 10931
8. Sanacora G., Kershaw M., Finkelstein J.A., and White J.D. Endocrinology 127 (1990) 730
9. Guan X.-M., Yu H., and Van der Ploeg L.H.T. Mol. Brain Res. 59 (1998) 273
10. Erickson J.C., Hollopeter G., and Palmiter R.D. Science 274 (1996) 1704
11. Blomqvist A.G., and Herzog H. Trends Neurosci. 20 (1997) 294
12. Gerald C., Walker M.W., Criscione L., Gustafson E.L., Batzl-Hartmann C., Smith K.E., Vaysse P., Durkin M.M., Laz T.M., Linemeyer D.L., Schaffhauser A.O., Whitebread S., Hofbauer K.G., Taber R.I., Branchchek T.A., and Weinshank R.L. Nature 382 (1996) 168
13. Galiano S., Erviti O., Pérez S., Moreno A., Juanenea L., Aldana I., and Monge A. Bioorg. Med. Chem. Lett. 14 (2004) 597
14. Juanenea L., Galiano S., Erviti O., Moreno A., Pérez S., Aldana I., and Monge A. Bioorg. Med. Chem. 12 (2004) 4717
15. Rueeger H., Gerspacher M., Buehlmayer P., Rigollier P., Yamaguchi Y., Schmidlin T., Whitebread S., Nuesslein-Hildesheim B., Nick H., and Cricione L. Bioorg. Med. Chem. Lett. 14 (2004) 2451
16. Aquino C.J., Ramanjulu J.M., Heyer D., Daniels A.J., Palazzo F., and Dezube M. Bioorg. Med. Chem. 12 (2004) 2691
17. Hammond M., Elliott R.L., Gillaspy M.L., Hager D.C., Hank R.F., LaFlamme J.A., Oliver R.M., DaSilva-Jardine P.A., Stevenson R.W., Mack C.M., and Cassella J.V. Bioorg. Med. Chem. Lett. 13 (2003) 1989
18. Islam I., Dhanoa D., Finn J., Du P., Walker M.W., Salon J.A., Zhang J., and Gluchowski C. Bioorg. Med. Chem. Lett. 12 (2002) 1767
19. Finn J., Pelham D., Walker M.W., and Gluchowski C. Bioorg. Med. Chem. Lett. 12 (2002) 1771
20. Tabuchi S., Itani H., Sakata Y., Oohashi H., and Satoh Y. Bioorg. Med. Chem. Lett. 12 (2002) 1171
21. Satoh Y., Hatori C., and Ito H. Bioorg. Med. Chem. Lett. 12 (2002) 1009
22. Itani H., Ito H., Sakata Y., Hatakeyama Y., Oohashi H., and Satoh Y. Bioorg. Med. Chem. Lett. 12 (2002) 757
23. Itani H., Ito H., Sakata Y., Hatakeyama Y., Oohashi H., and Satoh Y. Bioorg. Med. Chem. Lett. 12 (2002) 799
24. Sato N., Takahashi T., Shibata T., Haga Y., Sakuraba A., Hirose M., Sato M., Nonoshita K., Koike Y., Kitazawa H., Fujino N., Ishii Y., Ishihara A., Kanatani A., and Fukami T. J. Med. Chem. 46 (2003) 666
25. Thavonekham B. Synthesis (1997) 1189
26. Elliott J.M., Broughton H., Cascieri M.A., Chicchi G., Huscroft I.T., Kurtz M., MacLeod A.M., Sadowski S., and Stevenson G.I. Bioorg. Med. Chem. Lett. 8 (1998) 1851
27. Wolfe J.P., Wagaw S., and Buchwald S.L. J. Am. Chem. Soc. 118 (1996) 7215
28. Meth-Cohn O., and Suschitzky H. J. Chem. Soc. (1964) 2609
29. Kanatani A., Ishihara A., Iwaasa H., Nakamura K., Okamoto O., Hidaka M., Ito J., Fukuroda T., MacNeil D.J., Van der Ploeg L.H.T., Ishii Y., Okabe T., Fukami T., and Ihara M. Biochem. Biophys. Res. Commun. 272 (2000) 169
30. Senga K., O'Brien D.E., Scholten M.B., Novinson T., Miller J.P., and Robins R.K. J. Med. Chem. 25 (1982) 243