Modulation of PPAR subtype selectivity. Part 2: Transforming PPARα/γ dual agonist into α selective PPAR agonist through bioisosteric modification

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 2, 2011, Pages 628-632

  Zaware, Pandurang ^a,b   Shah, Shailesh R ^b   Pingali, Harikishore ^a   Makadia, Pankaj ^a   Thube, Baban ^a   Pola, Suresh ^a   Patel, Darshit ^a   Priyadarshini, Priyanka ^a   Suthar, Dinesh ^a   Shah, Maanan ^a   Jamili, Jeevankumar ^a   Sairam, Kalapatapu V V M ^a   Giri, Suresh ^a   Patel, Lala ^a   Patel, Harilal ^a   Sudani, Hareshkumar ^a   Patel, Hiren ^a   Jain, Mukul ^a   Patel, Pankaj ^a   Bahekar, Rajesh ^a  

^a ZYDUS RESEARCH CENTRE   (India)

^b M S UNIVERSITY OF BARODA   (India)

Author keywords

1,3 Dioxane r 2 carboxylic acid; Metabolic disorders; Oxime; PPAR agonist; Type 2 diabetes

Indexed keywords

2 METHYL C 5 (4 (2 [( (1 (PYRIDIN 3 YL)ETHYLIDENE]AMINO)OXY]ETHOXY)BENZYL) 1,3 DIOXANE R 2 CARBOXYLIC ACID; 2 METHYL C 5 (4 (2 [( [1 (4 (METHYLSULFONYL)PHENYL]ETHYLIDENE)AMINO]OXY)ETHOXY)BENZYL) 1,3 DIOXANE R 2-CARBOXYLIC ACID; 2 METHYL C 5 (4 (2 [( [1 (4 (TRIFLUOROMETHOXY)PHENYL]ETHYLIDENE)AMINO]OXY)ETHOXY)BENZYL) 1,3 DIOXANE R 2 CARBOXYLIC ACID; 2 METHYL C 5 (4 (2 [( [1 (4 (TRIFLUOROMETHYL)PHENYL] ETHYLIDENE)AMINO]OXY)ETHOXY)BENZYL) 1,3 DIOXANE R 2 CARBOXYLIC ACID; 2 METHYL C 5 (4 (2 [( [1 (5,6,7,8 TETRAHYDRONAPHTHALEN 2 YL)ETHYLIDENE]AMINO)OXY]ETHOXY)BENZYL) 1,3 DIOXANE R 2 CARBOXYLIC ACID; 2 METHYL C 5 (4 (2 [( [1 (NAPHTHALEN 2 YL)ETHYLIDENE]AMINO)OXY]ETHOXY)BENZYL) 1,3 DIOXANE R 2 CARBOXYLIC ACID; 2 METHYL C 5 (4 (2 [( [1 (P TOLYL)ETHYLIDENE]AMINO)OXY]ETHOXY)BENZYL) 1,3 DIOXANE R 2 CARBOXYLIC ACID; 2 METHYL C 5 (4 (2 [( [1 PHENYLETHYLIDENE]AMINO)OXY]ETHOXY)BENZYL) 1,3 DIOXANE R 2 CARBOXYLIC ACID; 2,2 DICHLORO 12 (4 CHLOROPHENYL)DODECANOIC ACID; [2 METHYL 4 [4 METHYL 2 (4 TRIFLUOROMETHYLPHENYL) 5 THIAZOLYLMETHYLTHIO]PHENOXY]ACETIC ACID; C 5 (4 (2 [( [1 (3,4 DIMETHOXYPHENYL)ETHYLIDENE]AMINO)OXY]ETHOXY)BENZYL) 2 METHYL 1,3 DIOXANE R 2 CARBOXYLIC ACID; C 5 (4 (2 [( [1 (4 FLUOROPHENYL)ETHYLIDENE)AMINO)OXY)ETHOXY)BENZYL) 2 METHYL 1,3 DIOXANE R 2 CARBOXYLIC ACID; C 5 (4 (2 [( [1 (4 METHOXYPHENYL)ETHYLIDENE]AMINO)OXY]ETHOXY)BENZYL) 2 METHYL; NS 220; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA AGONIST; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA AGONIST; ROSIGLITAZONE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG MECHANISM; DRUG SELECTIVITY; HYDROGEN BOND; IN VITRO STUDY; MALE; MAXIMUM PLASMA CONCENTRATION; MOLECULAR DOCKING; NONHUMAN; RAT;

ANIMALS; CARBOXYLIC ACIDS; CELL LINE; DIOXANES; HUMANS; HYPOGLYCEMIC AGENTS; HYPOLIPIDEMIC AGENTS; MALE; MICE; MODELS, MOLECULAR; OXIMES; PPAR ALPHA; PPAR GAMMA; RATS; RATS, SPRAGUE-DAWLEY; RATS, WISTAR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 78651283527     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.12.032     Document Type: Article

References (35)

1. D.H.V. Raalte, M. Pritchard, P.H. Li, and K.M. Wasan Pharm. Res. 21 2004 1531
2. T.M. Willson, P.J. Brown, D.D. Sternbach, and B.R. Henke J. Med. Chem. 43 2000 527
3. U. Kintscher, and R.E. Law Am. J. Physiol. Endocrinol. Metab. 288 2005 E287
4. P.A. Sarafidis Fundam. Clin. Pharmacol. 22 2008 247
5. B.R. Henke J. Med. Chem. 47 2004 4118
6. B.R. Henke, S.G. Blanchard, M.F. Brackeen, K.K. Brown, J.E. Cobb, J.L. Collins, W.W. Harrington, M.A. Hashim, E.A. Hull-Ryde, I. Kaldor, S.A. Kliewer, D.H. Lake, L.M. Leesnitzer, J.M. Lehmann, J.M. Lenhard, L.A. Orband- Miller, J.F. Miller, R.A. Mook, S.A. Noble, W. Oliver, D.J. Parks, K.D. Plunket, J.R. Szewczyk, and T.M. Willson J. Med. Chem. 41 1998 5020
7. B.B. Lohray, V.B. Lohray, A.C. Bajji, S. Kalchar, R.R. Poondra, S. Padakanti, R. Chakrabarti, R.K. Vikramadithyan, P. Misra, S. Juluri, N.V.S.R. Mamidi, and R. Rajagopalan J. Med. Chem 44 2001 2675
8. B.D. Hegarty, S.M. Furler, N.D. Oakes, E.W. Kraegen, and G.J. Cooney Endocrinology 145 2004 3158
9. P.T. Cheng, G. Chandrasena, and S. Chen Diabetes 51 2002 A94
10. W.R. Oliver Jr., J.L. Shenk, M.R. Snaith, C.S. Russell, K.D. Plunket, N.L. Bodkin, M.C. Lewis, D.A. Winegar, M.L. Sznaidman, M.H. Lambert, H.E. Xu, D.D. Sternbach, S.A. Kliewer, B.C. Hansen, and T.M. Willson Proc. Natl. Acad. Sci. 98 2001 5306
11. J.P. Mogensen, L. Jeppesen, P.S. Bury, I. Pettersson, J. Fleckner, J. Nehlin, K.S. Frederiksen, T. Albrektsen, N. Din, S.B. Mortensen, L.A. Svensson, K. Wassermann, E.M. Wulff, L. Ynddal, and P. Sauerberg Bioorg. Med. Chem. Lett. 13 2003 257
12. P.L. Feldmana, M.H. Lambertb, and B.R. Henke Curr. Top. Med. Chem. 8 2008 728
13. A. Rubenstrunk, R. Hanf, D.W. Hum, J. Fruchart, and B. Staels Biochim. Biophys. Acta 1771 2007 1065
14. M. Guerre-Millo, P. Gervois, E. Raspe, L. Madsen, P. Poulain, B. Derudas, J. Herbert, D. Winegar, T. Willson, J. Fruchart, and B. Staels J. Biol. Chem. 275 2000 16638
15. J. Ye, P. Doyle, M. Iglesias, D. Watson, G. Cooney, and E. Kraegen Diabetes 50 2001 411
16. P.J. Brown, D.A. Winegar, K.D. Plunket, L.B. Moore, M.C. Lewis, J.G. Wilson, S.S. Sundseth, C.S. Koble, Z. Wu, J.M. Chapman, J.M. Lehmann, S.A. Kliewer, and T.M. Willson J. Med. Chem. 42 1999 3785
17. P.J. Brown, L.W. Stuart, K.P. Hurley, M.C. Lewis, D.A. Winegar, J.G. Wilson, W.O. Wilkison, O.R. Ittoop, and T.M. Willson Bioorg. Med. Chem. Lett. 11 2001 1225
18. H. Miyachi, M. Nomura, T. Tanase, Y. Takahashi, T. Ide, M. Tsunoda, K. Murakami, and K. Awano Bioorg. Med. Chem. Lett. 12 2002 77
19. Y. Xu, D. Mayhugh, A. Saeed, X. Wang, R.C. Thompson, S.J. Dominianni, R.F. Kauffman, J. Singh, J.S. Bean, W.R. Bensch, R.J. Barr, J. Osborne, C. Montrose-Rafizadeh, R.W. Zink, N.P. Yumibe, N. Huang, D. Luffer-Atlas, D. Rungta, D.E. Maise, and N.B. Mantlo J. Med. Chem. 46 2003 5121
20. T. Asaki, T. Aoki, T. Hamamoto, Y. Sugiyama, S. Ohmachi, K. Kuwabara, K. Murakami, and M. Todo Bioorg. Med. Chem. 16 2008 981
21. S.A. Schafer, B.C. Hansen, A. Volkl, H.D. Fahimi, and J. Pill Biochem. Pharmacol. 682 2004 239
22. B.B. Lohray, V. Bhushan, A.S. Reddy, P.B. Rao, N.J. Reddy, P. Harikishore, R.K. Vikramadityan, R. Chakrabarti, R. Rajagopalan, and K. Katneni J. Med. Chem. 42 1999 2569
23. K.A. Reddy, B.B. Lohray, V. Bhushan, A.S. Reddy, P. Harikishore, V.V. Rao, V. Saibaba, A.C. Bajji, B.M. Rajesh, K.V. Reddy, R. Chakrabarti, and R. Rajagopalan Bioorg. Med. Chem. Lett. 8 1998 999
24. H. Pingali, M. Jain, S. Shah, P. Makadia, P. Zaware, A. Goel, M. Patel, S. Giri, H. Patel, and P. Patel Bioorg. Med. Chem. 16 2008 7117
25. H. Pingali, M. Jain, S. Shah, S. Basu, P. Makadia, A. Goswami, P. Zaware, P. Patil, A. Godha, S. Giri, A. Goel, M. Patel, H. Patel, and P. Patel Bioorg. Med. Chem. Lett. 18 2008 5586
26. C. Tudor, J.N. Feige, H. Pingali, V.B. Lohray, W. Wahli, B. Desvergne, Y. Engelborghs, and L. Gelman J. Biol. Chem. 282 2007 4417
27. T.M. Willson, P.J. Brown, D.D. Sternbach, and B.R. Henke J. Med. Chem. 43 2000 527
28. H. Pingali, M. Jain, S. Shah, P. Patil, P. Makadia, P. Zaware, V.V.M.S. Kalapatapu, J. Jamili, A. Goel, M. Patel, and P. Patel Bioorg. Med. Chem. Lett 18 2008 6471
29. H. Pingali, M. Jain, S. Shah, P. Patil, P. Zaware, P. Makadia, S. Pola, B. Thube, D. Patel, P. Patil, P. Priyadarshini, D. Suthar, M. Shah, S. Giri, and P. Patel Bioorg. Med. Chem. Lett 20 2010 1156
30. H. Yanagisawa, M. Takamura, E. Yamada, S. Fujita, T. Fujiwara, M. Yachi, A. Isobe, and Y. Hagisawa Bioorg. Med. Chem. Lett. 10 2000 373
31. T. Harabe, T. Matsumoto, and T. Shioiri Tetrahedron Lett. 48 2007 1443
32. 3)
33. glide 5.6, Schrodinger, LLC, New York, NY, 2010.
34. LigPrep 2.6, Schrodinger, LLC, New York, NY, 2010.
35. V. Zoete, A. Grosdidier, and O. Michielin Biochim. Biophys. Acta 1771 2007 915