Synthesis and structure-activity relationships of 2-acylamino-4,6-diphenylpyridine derivatives as novel antagonists of GPR54

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 11, 2010, Pages 3841-3859

  Kobayashi, Toshitake ^a   Sasaki, Satoshi ^a   Tomita, Naoki ^a   Fukui, Seiji ^a   Kuroda, Noritaka ^a   Nakayama, Masaharu ^a   Kiba, Atsushi ^a   Takatsu, Yoshihiro ^a   Ohtaki, Tetsuya ^a   Itoh, Fumio ^a   Baba, Atsuo ^a  

^a TAKEDA PHARMACEUTICAL COMPANY LIMITED   (Japan)

Author keywords

2 Acylamino 4,6 diphenylpyridine; GPR54 antagonist; Kisspeptin; Metastin

Indexed keywords

1 [2 (ETHOXYMETHOXY) 4 FLUOROPHENYL]ETHANONE; 1 [2 (ETHOXYMETHOXY) 4 METHYLPHENYL]ETHANONE; 1 [2 (METHOXYMETHOXY)PHENYL]ETHANONE; 1 [2 (METHOXYMETHOXY)PHENYL]PROPAN 1 ONE; 1 [4 BROMO 2 (METHOXYMETHOXY)PHENYL]ETHANONE; 1 [4 CHLORO 2 (METHOXYMETHOXY)PHENYL]ETHANONE; 1 [4 FLUORO 2 (METHOXYMETHOXY)PHENYL]ETHANONE; 1 [4 METHOXY 2 (METHOXYMETHOXY)PHENYL]ETHANONE; 1 [5 CHLORO 2 (METHOXYMETHOXY)PHENYL]ETHANONE; 1 [5 METHOXY 2 (METHOXYMETHOXY)PHENYL]ETHANONE; 2 ACYLAMINO 4,6 DIPHENYLPYRIDINE DERIVATIVE; 2 AMINO 6 (3 {[TERT BUTYL(DIMETHYL)SILYL]OXY}PHENYL) 4 (3 NITROPHENYL)PYRIDINE 3 CARBONITRILE; 2 AMINO 6 (4 {[TERT BUTYL(DIMETHYL)SILYL]OXY}PHENYL) 4 (3 NITROPHENYL)PYRIDINE 3 CARBONITRILE; 2 AMINO 6 [2 (ETHOXYMETHOXY) 4 FLUOROPHENYL] 4 (3 NITROPHENYL)PYRIDINE 3 CARBONITRILE; 2 AMINO 6 [2 (ETHOXYMETHOXY) 4 METHYLPHENYL] 4 (3 NITROPHENYL)PYRIDINE 3 CARBONITRILE; 2 AMINO 6 [2 (METHOXYMETHOXY)PHENYL] 5 METHYL 4 (3 NITROPHENYL)PYRIDINE 3 CARBONITRILE; 2 AMINO 6 [4 BROMO 2 (METHOXYMETHOXY)PHENYL] 4 (3 NITROPHENYL)PYRIDINE 3 CARBONITRILE; 2 AMINO 6 [4 CHLORO 2 (METHOXYMETHOXY)PHENYL] 4 (3 NITROPHENYL)PYRIDINE 3 CARBONITRILE; 2 AMINO 6 [4 FLUORO 2 (METHOXYMETHOXY)PHENYL] 4 (3 NITROPHENYL)PYRIDINE 3 CARBONITRILE; 2 AMINO 6 [4 METHOXY 2 (METHOXYMETHOXY)PHENYL] 4 3 NITROPHENYL)PYRIDINE 3 CARBONITRILE; 2 AMINO 6 [5 CHLORO 2 (METHOXYMETHOXY)PHENYL] 4 (3 NITROPHENYL)PYRIDINE 3 CARBONITRILE; 2 AMINO 6 [5 METHOXY 2 (METHOXYMETHOXY)PHENYL] 4 (3 NITROPHENYL)PYRIDINE 3 CARBONITRILE; METHYL 2 {2 AMINO 3 CYANO 6 [2 (METHOXYMETHOXY) PHENYL]PYRIDIN 4 YL}BENZOATE; METHYL 3 {2 AMINO 3 CYANO 6 [2 (METHOXYMETHOXY) PHENYL]PYRIDIN 4 YL}BENZOATE; METHYL 3 {2 AMINO 3 CYANO 6 [4 FLUORO 2 (METHOXYMETHOXY)PHENYL]PYRIDIN 4 YL}BENZOATE; METHYL 4 {2 AMINO 3 CYANO 6 [2 (METHOXYMETHOXY) PHENYL]PYRIDIN 4 YL}BENZOATE; N [6 (2 {[TERT BUTYL(DIMETHYL)SILYL]OXY}PHENYL) 3 CYANO 4 (3 NITROPHENYL)PYRIDIN 2 YL]THIOPHENE 2 CARBOXAMIDE; N [6 (3 {[TERT BUTYL(DIMETHYL)SILYL]OXY}PHENYL) 3 CYANO 4 (3 NITROPHENYL)PYRIDIN 2 YL]THIOPHENE 2 CARBOXAMIDE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; ARTICLE; BINDING ASSAY; CALCIUM MOBILIZATION; CELL ASSAY; CELL FUNCTION; CONTROLLED STUDY; DRUG ANTAGONISM; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

ANIMALS; CHO CELLS; CRICETINAE; CRICETULUS; HUMANS; INHIBITORY CONCENTRATION 50; PYRIDINES; RECEPTORS, G-PROTEIN-COUPLED; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77953135028     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.04.036     Document Type: Article

References (26)

1. Reviews:. Smith J.T., Clifton D.K., and Steiner R.A. Reproduction 131 (2006) 623
2. Dungan H.M., Clifton D.K., and Steiner R.A. Endocrinology 147 (2006) 1154
3. Lee D.K., Nguyen T., O'Neill G.P., Cheng R., Liu Y., Howard A.D., Coulombe N., Tan C.P., Tang-Nguyen A.-T., George S.R., and O'Dowd B.F. FEBS Lett. 446 (1999) 103
4. Muir A.I., Chamberlain L., Elshourbagy N.A., Michalovich D., Moore D.J., Calamari A., Szekeres P.G., Sarau H.M., Chambers J.K., Murdock P., Steplewski K., Shabon U., Miller J.E., Middleton S.E., Darker J.G., Larminie C.G.C., Wilson S., Bergsma D.J., Emson P., Faull R., Philpott K.L., and Harrison D.C. J. Biol. Chem. 276 (2001) 28969
5. Ohtaki T., Shintani Y., Honda S., Matsumoto H., Hori A., Kanehashi K., Terao Y., Kumano S., Takatsu Y., Masuda Y., Ishibashi Y., Watanabe T., Asada M., Yamada T., Suenaga M., Kitada C., Usuki S., Kurokawa T., Onda H., Nishimura O., and Fujino M. Nature 411 (2001) 613
6. Kotani M., Detheux M., Vandenbogaerde A., Communi D., Vanderwinden J.-M., Poul E.L., Brezillon S., Tyldesley R., Suarez-Huerta N., Vandeput F., Blanpain C., Schiffmann S.N., Vassart G., and Parmentier M. J. Biol. Chem. 276 (2001) 34631
7. Seminara S.B., Messager S., Chatzidaki E.E., Thresher R.R., Acierno Jr. J.S., Shagoury J.K., Bo-Abbas Y., Kuohung W., Schwinof K.M., Hendrick A.G., Zahn D., Dixon J., Kaiser U.B., Slaugenhaupt S.A., Gusella J.F., O'Rahilly S., Carlton M.B.L., Crowley Jr. W.F., Aparicio S.A.J.R., and Colledge W.H. N. Eng. J. Med. 349 (2003) 1614
8. Funes S., Hedrick J.A., Vassileva G., Markowitz L., Abbondanzo S., Golovko A., Yang S., Monsma F.J., and Gustafson E.L. Biochem. Biophys. Res. Commun. 312 (2003) 1357
9. de Roux N., Genin E., Carel J.C., Matsuda F., Chaussain J.L., and Milgrom E. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 10972-10976
10. Matsui H., Takatsu Y., Kumano S., Matsumoto H., and Ohtaki T. Biochem. Biophys. Res. Commun. 320 (2004) 383
11. Thompson E.L., Patterson M., Murphy K.G., Smith K.L., Dhillo W.S., Todd J.F., Ghatei M.A., and Bloom S.R. J. Neuroendocrinol. 16 (2004) 850
12. Navarro V.M., Castellano J.M., Fernandez-Fernandez R., Barreiro M.L., Roa J., Sanchez-Criado J.E., Aguilar E., Dieguez C., Pinilla L., and Tena-Sempere M. Endocrinology 145 (2004) 4565
13. Navarro V.M., Castellano J.M., Fernandez-Fernandez R., Tovar S., Roa J., Mayen A., Nogueiras R., Vazquez M.J., Barreiro M.L., Magni P., Aguilar E., Dieguez C., Pinilla L., and Tena-Sempere M. Endocrinology 146 (2005) 156
14. Navarro V.M., Castellano J.M., Fernandez-Fernandez R., Tovar S., Roa J., Mayen A., Barreiro M.L., Casanueva F.F., Aguilar E., Dieguez C., Pinilla L., and Tena-Sempere M. Endocrinology 146 (2005) 1689
15. Gottsch M.L., Cunningham M.J., Smith J.T., Popa S.M., Acohido B.V., Crowley W.F., Seminara S., Clifton D.K., and Steiner R.A. Endocrinology 145 (2004) 4073
16. Messager S., Chatzidaki E.E., Ma D., Hendrick A.G., Zahn D., Dixon J., Thresher R.R., Malinge I., Lomet D., Carlton M.B.L., Colledge W.H., Caraty A., and Aparicio S.A.J.R. Proc. Natl. Acad. Sci. U.S.A. 102 (2005) 1761
17. Sahahab M.M., Seminara S.B., Crowley W.F., Ojeda S.R., and Plant T.M. Proc. Natl. Acad. Sci. U.S.A. 102 (2005) 2129
18. Dhillo W.S., Chaudhri O.B., Patterson M., Thompson E.L., Murphy K.G., Badman M.K., McGowan B.M., Amber V., Patel S., Ghatei M.A., and Bloom S.R. J. Clin. Endocrinol. Metab. 12 (2005) 6609
19. Irwig M.S., Fraley G.S., Smith J.T., Acohido B.V., Popa S.M., Cunningham M.J., Gottsch M.L., Clifton D.K., and Steiner R.A. Neuroendocrinology 80 (2004) 264
20. Kinoshita M., Tsukamura H., Adachi S., Matsui H., Uenoyama Y., Iwata K., Yamada S., Inoue K., Ohtaki T., Matsumoto H., and Maeda K. Endocrinology 146 (2005) 4431
21. Peptide GPR54 antagonists were recently reported:. Roseweir A.K., Kauffman A.S., Smith J.T., Guerriero K.A., Morgan K., Pielecka-Fortuna J., Pienda R., Gottsch M.L., Tena-Sempere M., Moenter S.M., Terasawa E., Clarke I.J., Steiner R.A., and Millar R.P. J. Neurosci. 29 (2009) 3920
22. 1H NMR spectrum:. Murata T., Shimada M., Sakakibara S., Yoshino T., Kadono H., Masuda T., Shimazaki M., Shintani T., Fuchikami K., Sakai K., Inbe H. Bioorg. Med. Chem. Lett. 13 5 (2003) 913
23. Aggarwal R., Birkbeck A.A., Giles R.G., Green I.R., Gruchlik Y., and Oosthuizen F.J. Aust. J. Chem. 56 (2003) 489
24. Xing X., Ho P., Bourquin G., Yen L.A., and Cuny G.D. Tetrahedron 59 (2003) 9961
25. Murata, T.; Sakakibara, S.; Yoshino, T.; Ikegami, Y.; Masuda, T.; Shimada, M.; Shintani, T.; Shimazaki, M.; Lowinger, T. B.; Ziegelbauer, K. B.; Fuchikami, K.; Umeda, M.; Komura, H.; Yoshida, N. WO 0244153, 2002.
26. Ohtaki T., Kumano S., Ishibashi Y., Ogi K., Matsui H., Harada M., Kitada C., Kurokawa T., Onda H., and Fujino M. J. Biol. Chem. 274 (1999) 37041