Modulation of PPAR receptor subtype selectivity of the ligands: Aliphatic chain vs aromatic ring as a spacer between pharmacophore and the lipophilic moiety

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 24, 2008, Pages 6471-6475

  Pingali, Harikishore ^a,b   Jain, Mukul ^a   Shah, Shailesh ^b   Patil, Pravin ^a   Makadia, Pankaj ^a   Zaware, Pandurang ^a   Sairam, Kalapatapu V V M ^a   Jamili, Jeevankumar ^a   Goel, Ashish ^a   Patel, Megha ^a   Patel, Pankaj ^a  

^a ZYDUS RESEARCH CENTRE   (India)

^b M S UNIVERSITY OF BARODA   (India)

Author keywords

Imiglitazar; Muraglitazar; Oxazole; PPAR agonist

Indexed keywords

AROMATIC COMPOUND; BENZENE DERIVATIVE; BUTYRIC ACID DERIVATIVE; CARBENE; CARBOXYLIC ACID DERIVATIVE; GLYCINE DERIVATIVE; IMIGLITAZAR; LIGAND; MURAGLITAZAR; NS 220; OXAZOLE DERIVATIVE; OXIME DERIVATIVE; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA AGONIST; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; HYDROGEN BOND; LIPOPHILICITY; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION;

BUTYRIC ACIDS; CHEMISTRY, PHARMACEUTICAL; DIOXANES; DRUG DESIGN; GLYCINE; HUMANS; HYDROGEN; HYDROGEN BONDING; LIGANDS; MODELS, CHEMICAL; OXAZOLES; PEROXISOME PROLIFERATOR-ACTIVATED RECEPTORS; PPAR ALPHA; TRANSCRIPTIONAL ACTIVATION;

EID: 56649086641     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.10.062     Document Type: Article

References (28)

1. Issemann I., and Green I. Nature 347 (1990) 645
2. Mangelsdorf D.J., and Evans R.M. Cell 83 (1995) 841
3. Willson T.M., Brown P.T., Sternbach D.D., and Henke B.R. J. Med. Chem. 43 (2000) 527
4. Kersten S., Desvergne B., and Wahli W. Nature 405 (2000) 421
5. Berger J.P., and Moller D.E. Annu. Rev. Med. 53 (2002) 409
6. Martin G., Schoonjans K., Staels B., and Auwerx J. Atherosclerosis 137 Suppl. (1998) S75
7. Rosen E.D., and Spiegelman B.M. J. Biol. Chem. 276 (2001) 37731
8. Torra I.P., Gervois P., and Staels B. Curr. Opin. Lipidol. 10 (1999) 151
9. Xu Y., Rito C.J., Etgen G.J., Ardecky R.J., Bean J.S., Bensch W.R., Bosley J.R., Broderick C.L., Brooks D.A., Dominianni S.J., Hahn P.J., Liu S., Mais D.E., Montrose-Rafizadeh C., Ogilvie K.M., Oldham B.A., Peters M., Rungta D.K., Stephenson G.A., Shuker A.J., Tripp A.E., Wilson S.B., Winneroski L.L., Zink R., Kauffman R.F., and McCarthy J.R. J. Med. Chem. 47 (2004) 2422
10. Marti{dotless} J.A., Brooks D.A., Prieto L., González R., Torrado A., Rojo I., Uralde B.L., Lamas C., Ferritto R., Marti{dotless}n-Ortega M.D., Agejas J., Parra F., Rizzo J.R., Rhodes G.A., Robey R.L., Alt C.A., Wendel S.R., Zhang T.Y., Reifel-Miller A., Montrose-Rafizadeh C., Brozinick J.T., Hawkins E., Misener E.A., Briere D.A., Ardecky R., Fraserd J.D., and Warshawsky A.M. Bioorg. Med. Chem. Lett. 15 (2005) 51
11. Lu Y., Guo Z., Guo Y., Feng J., and Chu F. Bioorg. Med. Chem. Lett. 16 (2006) 915
12. Das S.K., Reddy K.A., Abbineni C., Iqbal J., Suresh J., Premkumar M., and Chakrabarthi R. Bioorg. Med. Chem. Lett. 13 (2003) 399
13. Madhavan G.R., Chakrabarthi R., Reddy K.A., Rajesh B.M., Balaraju V., Rao P.B., Rajagopalan R., and Iqbal J. Bioorg. Med. Chem. 14 (2006) 584
14. Henke B.R., Blanchard S.G., Brackeen M.F., Brown K.K., Cobb J.E., Collins J.L., Harrington Jr. W.W., Hashim M.A., Hull-Ryde E.A., Kaldor I., Kliewer S.A., Lake D.H., Leesnitzer L.M., Lehmann J.M., Lenhard J.M., Orband-Miller L.A., Miller J.F., Mook R.A., Noble S.A., Oliver W., Parks D.J., Plunket K.D., Szewczyk J.R., and Willson T.M. J. Med. Chem. 41 (1998) 5020
15. Lohray B.B., Lohray V.B., Bajji A.C., Kalchar S., Poondra R.R., Padakanti S., Chakrabarti R., Vikramadithyan R.K., Misra P., Juluri S., Mamidi N.V.S.R., and Rajagopalan R. J. Med. Chem. 44 (2001) 2675
16. Hegarty B.D., Furler S.M., Oakes N.D., Kraegen E.W., and Cooney G.J. Endocrinology 145 (2004) 3158
17. Devasthale P.V., Chen S., Jeon Y., Qu F., Shao C., Wang W., Zhang H., Cap M., Farrelly D., Golla R., Grover G., Harrity T., Ma Z., Moore L., Ren J., Seethala R., Cheng L., Sleph P., Sun W., Tieman A., Wetterau J.R., Doweyko A., Chandrasena G., Chang S.Y., Humphreys W.G., Sasseville V.G., Biller S.A., Ryono D.E., Selan F., Hariharan N., and Cheng P.T.W. J. Med. Chem. 48 (2004) 2248
18. Guerre-Millo M., Gervois P., Raspe E., Madsen L., Poulain P., Derudas B., Herbert J., Winegar D., Willson T., Fruchart J., and Staels B. J. Biol. Chem. 275 (2000) 16638
19. Ye J., Doyle P., Iglesias M., Watson D., Cooney G., and Kraegen E. Diabetes 50 (2001) 411
20. Lohray B.B., Bhushan V., Reddy A.S., Rao P.B., Reddy N.J., Harikishore P., Vikramadityan R.K., Chakrabarti R., Rajagopalan R., and Katneni K. J. Med. Chem. 42 (1999) 2569
21. Reddy K.A., Lohray B.B., Bhushan V., Reddy A.S., Harikishore P., Rao V.V., Saibaba V., Bajji A.C., Rajesh B.M., Reddy K.V., Chakrabarti R., and Rajagopalan R. Bioorg. Med. Chem. Lett. 8 (1998) 999
22. Tudor C., Feige J.N., Pingali H., Lohray V.B., Wahli W., Desvergne B., Engelborghs Y., and Gelman L. J. Biol. Chem. 282 (2007) 4417
23. Pingali H., Jain M., Shah S., Makadia P., Zaware P., Goel A., Patel M., Giri S., Patel H., and Patel P. Bioorg. Med. Chem. 16 (2008) 7117
24. Asaki T., Aoki T., Hamamoto T., Sugiyama Y., Ohmachi S., Kuwabara K., Murakami K., and Todo M. Bioorg. Med. Chem. 16 (2008) 981
25. Imoto H., Sugiyama Y., Kimura H., and Momose Y. Chem. Pharm. Bull. 51 (2003) 138
26. Brooks D.A., Etgen G.J., Rito C.J., Shuker A.J., Dominianni S.J., Warshawsky A.M., Ardecky R., Paterniti J.R., Tyhonas J., Karanewsky D.S., Kauffman R.F., Broderick C.L., Oldham B.A., Montrose-Rafizadeh C., Winneroski L.L., Faul M.M., and McCarthy J.R. J. Med. Chem. 44 (2001) 2061
27. +;
28. Xu H.E., Lambert M.H., Montana V.G., Plunket K.D., Moore L.B., Collins J.L., Oplinger J.A., Kliewer S.A., Gampe R.T., McKee D.D., Moore J.T., and Willson T.M. Proc. Natl. Acad. U.S.A. 98 (2001) 13919