Synthesis and structure-activity relationship of novel indene N-oxide derivatives as potent peroxisome proliferator activated receptor γ (PPARγ) agonists

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 18, 2007, Pages 5239-5244

  Ahn, Jin Hee ^a   Shin, Mi Sik ^a   Jung, Sun Ho ^a   Kim, Jin Ah ^a   Kim, Hye Min ^a   Kim, Se Hoan ^a   Kang, Seung Kyu ^a   Kim, Kwang Rok ^a   Rhee, Sang Dal ^a   Park, Sung Dae ^b   Lee, Jae Mok ^c   Lee, Jeong Hyung ^d   Cheon, Hyae Gyeong ^a   Kim, Sung Soo ^a  

^a Korea Research Institute of Chemical Technology   (South Korea)

^b Jeil Pharmaceutical Co Ltd   (South Korea)

^c CJ Corporation   (South Korea)

^d Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

Author keywords

Diabetes; Indene N oxide; PPAR

Indexed keywords

INDENE DERIVATIVE; INDENE N OXIDE DERIVATIVE; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA AGONIST; PIOGLITAZONE; ROSIGLITAZONE; UNCLASSIFIED DRUG;

ADIPOGENESIS; ARTICLE; CONTROLLED STUDY; DOWN REGULATION; DRUG STRUCTURE; DRUG SYNTHESIS; EDEMA; FATTY ACID TRANSPORT; GLUCOSE HOMEOSTASIS; HUMAN; INSULIN SENSITIVITY; LIVER TOXICITY; NON INSULIN DEPENDENT DIABETES MELLITUS; SIDE EFFECT; STRUCTURE ACTIVITY RELATION; UPREGULATION; WEIGHT GAIN; X RAY CRYSTALLOGRAPHY;

INDENES; PPAR GAMMA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34547865706     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.06.073     Document Type: Article

References (21)

1. Picard F., and Auwerx J. Annu. Rev. Nutr. 22 (2002) 167
2. Demer L. Circ. Res. 90 (2002) 241
3. Mukherjee R. Drug News Perspect. 15 (2002) 261
4. Berger J., and Moller D.E. Annu. Rev. Med. 53 (2002) 409
5. Walczak R., and Tontonoz P. J. Lipid Res. 43 (2002) 77
6. Yamauchi T., Kamon J., Waki H., Murakami K., Motojima K., Komeda K., Ide T., Kubota N., Terauchi Y., Tobe K., Miki H., Tsuchida A., Akanuma Y., Nagai R., Kimura S., and Kadowaki T. J. Biol. Chem. 276 (2001) 41245
7. Wagstaff A.J., and Goa K.L. Drugs 62 (2002) 1805
8. Diamant M., and Heine R.J. Drugs 63 (2003) 1373
9. Chilcott J., Tappenden P., Jones M.L., and Wight J.P. Clin. Ther. 23 (2001) 1792
10. Grossman L.D. PharmacoEconomics 20 (2002) 1
11. 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., Ghandreasena G., Chang S.Y., Humphreys W.G., Sasseville V.G., Biller S.A., Ryono D.E., Selan F., Hariharan N., and Cheng R.T.W. J. Med. Chem. 48 (2005) 2248
12. Henke B.R. J. Med. Chem. 47 (2004) 4118
13. Nissen S.E., Wolski K., and Topol E.J. JAMA 294 (2005) 2581
14. Jennermann C., Triantafillou J., Cowan D., Pennink B.G.A., Connolly K.M., and Morris D.C. J. Bon. Miner. Res. 10 (1995) S361
15. Gimble J.M., Robinson C.E., Wu X., and Kelly K.A. Bone 19 (1996) 421
16. Berger J.P., Petro A.E., Macnaul K.L., Kelly L.J., Zhang B.B., Richards K., Elbrecht A., Johnson B.A., Zhou G., Doebber T.W., Biswas C., Parikh M., Sharma N., Tanen M.R., Thompson G.M., Ventre J., Adams A.D., Mosley R., Surwit R.S., and Moller D.E. Mol. Endocrinol. 17 (2003) 662
17. Acton J.J., Black R.M., Jones A.B., Moller D.E., Colwell L., Doebber T.W., MacNaul K.L., Berger J., and Wood H.B. Bioorg. Med. Chem. Lett. 15 (2005) 357
18. Liu K., Black R.M., Acton J.J., Mosley R., Debenham S., Abola R., Yang M., Tschirret-Guth R., Dolwell L., Liu C., Wu M., Wand C.F., MacNau K.L., McCann M.E., Moller D.E., Berger J.P., Meinke P.T., Jones A.B., and Wood H.B. Bioorg. Med. Chem. Lett. 15 (2005) 2437
19. Ahn J.H., Shin M.S., Jung S.H., Kang S.K., Kim K.R., Rhee S.D., Jung W.H., Yang S.D., Kim S.J., Woo J.R., Lee J.H., Cheon H.G., and Kim S.S. J. Med. Chem. 49 (2006) 4781
20. Kim K.R., Lee J.H., Kim S.J., Rhee S.D., Jung W.H., Yang S.D., Kim S.S., Ahn J.H., and Cheon H.G. Biochem.Pharmacol. 72 (2006) 446
21. Detailed synthetic procedures: Please see our patent (WO 2005100303).