Design, synthesis, biological evaluation and docking studies of pterostilbene analogs inside PPARα

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 7, 2008, Pages 3800-3808

  Mizuno, Cassia S ^a   Ma, Guoyi ^b   Khan, Shabana ^b   Patny, Akshay ^c   Avery, Mitchell A ^c   Rimando, Agnes M ^a  

^a NATURAL PRODUCTS UTILIZATION RESEARCH UNIT   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

^c Laboratory for Applied Drug Design and Synthesis   (United States)

Author keywords

Dyslipidemia; Peroxisome proliferator activated receptor; Pterostilbene; Resveratrol

Indexed keywords

3,5 BIS(TERT BUTYLDIMETHYLSILYLOXY)BENZALDEHYDE; 4 (3,5 DIMETHOXYPHENETHYL)PHENOL; 4 (3,5 DIMETHOXYSTYRYL)PHENYLDIHYDROGEN PHOSPHATE; 5 (4 METHOXYSTYRYL)BENZENE 1,3 DIOL; CIPROFIBRATE; GW 409544; METHYL 4 (3,5 DIMETHOXYSTYRYL)BENZOATE; METHYL 4 (4 METHOXYSTYRYL)BENZOATE; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA AGONIST; PTEROSTILBENE; PTEROSTILBENE DERIVATIVE; STILBENE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CHEMICAL INTERACTION; CONTROLLED STUDY; DRUG DESIGN; DRUG PROTEIN BINDING; DRUG SYNTHESIS; HYDROGEN BOND; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; WITTIG REACTION;

ANIMALS; CELL LINE, TUMOR; DRUG DESIGN; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PPAR ALPHA; PROTEIN BINDING; RATS; STILBENES;

ANIMALIA;

EID: 41649120931     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.01.051     Document Type: Article

References (25)

1. Stivala L.A., Savio M., Carafoli F., Perucca P., Bianchi L., Maga G., Forti L., Pagnoni U.M., Albini A., Prosperi E., and Vannini V. J. Biol. Chem. 276 (2001) 22586
2. Kimura Y., Okuda H., and Arichi S. Biochim. Biophys. Acta 834 (1985) 275
3. Mannila E., Talvitie A., and Kolehmainen E. Phytochemistry 33 (1993) 813
4. Mahady G.B., Pendland S.L., and Chadwick L.R. Am. J. Gastroenterol. 98 (2003) 1440
5. Creasy L.L., and Coffee M. J. Am. Soc. Hortic. Sci. 113 (1988) 230
6. Chung M.I., Teng C.M., Cheng K.L., Ko F.N., and Lin C.N. Planta Med. 58 (1992) 274
7. Inamori Y., Kubo M., Tsujibo H., Ogawa M., Saito Y., Miki Y., and Takemura S. Chem. Pharm. Bull. 35 (1987) 887
8. Schneider Y., Duranton B., Gosse F., Schleiffer R., Seiler N., and Raul F. Nutr. Cancer 39 (2001) 102
9. Jang M., Cai L., Udeani G.O., Slowing K.V., Thomas C.F., Beecher C.W., Fong H.H., Farnsworth N.R., Kinghorn A.D., Mehta R.G., Moon R.C., and Pezzuto J.M. Science 275 (1997) 218
10. Jang J.-H., Han S.-S., and Surh Y.-J. R. Soc. Chem. Spec. Pub. 255 (2000) 230
11. Burns J., Yokota T., Ashihara H., Lean M.E.J., and Crozier A. J. Agric. Food. Chem. 50 (2002) 3337
12. Rimando A.M., Kalt W., Magee J.B., Dewey J., and Ballington J.R. J. Agric. Food. Chem. 52 (2004) 4713
13. Hegsted D.M., and Ausman L.M. J. Nutr. 118 (1988) 1184
14. Renaud S., and de Lorgeril M. Lancet 339 (1992) 1523
15. Fauconneau B., Waffo-Teguo P., Huguet F., Barrier L., Decendit A., and Merillon J. Life Sci. 61 (1997) 2103
16. Frankel E.N., Waterhouse A.L., and Kinsella J.E. Lancet 341 (1993) 1103
17. Belguendouz L., Fremont L., and Linard A. Biochem. Pharmacol. 53 (1997) 1347
18. Arichi H., Kimura Y., Okuda H., Baba K., Kozawa M., and Arichi S. Chem. Pharm. Bull. 30 (1982) 1766
19. Rimando A.M., Nagmani R., Feller D.R., and Yokoyama W. J. Agric. Food. Chem. 53 (2005) 3403
20. Desai R.C., Metzger E., Santini C., Meinke P.T., Heck J.V., Berger J.P., MacNaul K.L., Cai T., Wright S.D., Agrawal A., Moller D.E., and Sahoo S.P. Bioorg. Med. Chem. Lett. 16 (2006) 1673
21. Pettit G.R., Grealish M.P., Jung M.K., Hamel E., Pettit R.K., Chapuis J.C., and Schmidt J.M. J. Med. Chem. 45 (2002) 2534
22. Roberti M., Pizzirani D., Simoni D., Rondanin R., Baruchello R., Bonora C., Buscemi F., Grimaudo S., and Tolomeo M. J. Med. Chem. 46 (2003) 3546
23. 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 Jr. R.T., McKee D.D., Moore J.T., and Willson T.M. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 13919
24. Collins, J. L.; Dezube, M.; Oplinger, J. A.; Willson, T. M. U.S. Patent 6,498,174 BI, 2000.
25. Gampe Jr. R.T., Montana V.G., Lambert M.H., Miller A.B., Bledsoe R.K., Milburn M.V., Kliewer S.A., Willson T.M., and Xu H.E. Mol. Cell 5 (2000) 545