메뉴 건너뛰기




Volumn 54, Issue 1, 2011, Pages 331-341

Design, synthesis, and structural analysis of phenylpropanoic acid-type PPARγ-selective agonists: Discovery of reversed stereochemistry-activity relationship

Author keywords

[No Author keywords available]

Indexed keywords

2 BENZYL 3 [3 (((4 ADAMANTAN 1 YL)BENZAMIDO)METHYL) 4 PROPOXYPHENYL]PROPANOIC ACID; LIGAND; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR AGONIST; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; UNCLASSIFIED DRUG;

EID: 78651111373     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101233f     Document Type: Article
Times cited : (22)

References (33)
  • 1
    • 0035976638 scopus 로고    scopus 로고
    • Nuclear receptors and lipid physiology: Opening the X-files
    • Chawla, A.; Repa, J. J.; Evans, R. M.; Mangelsdorf, D. J. Nuclear receptors and lipid physiology: opening the X-files Science 2001, 294, 1866-1870
    • (2001) Science , vol.294 , pp. 1866-1870
    • Chawla, A.1    Repa, J.J.2    Evans, R.M.3    Mangelsdorf, D.J.4
  • 2
    • 0027194474 scopus 로고
    • Systematic analytical chemistry/cell assay approach to isolate activators of orphan nuclear receptors from biological extracts: Characterization of peroxisome proliferator-activated receptor activators in plasma
    • Banner, C. D.; Göttlicher, M.; Widmark, E.; Sjövall, J.; Rafter, J. J.; Gustafsson, J. A. Systematic analytical chemistry/cell assay approach to isolate activators of orphan nuclear receptors from biological extracts: characterization of peroxisome proliferator-activated receptor activators in plasma J. Lipid Res. 1993, 34, 1583-1591
    • (1993) J. Lipid Res. , vol.34 , pp. 1583-1591
    • Banner, C.D.1    Göttlicher, M.2    Widmark, E.3    Sjövall, J.4    Rafter, J.J.5    Gustafsson, J.A.6
  • 3
    • 0030047806 scopus 로고    scopus 로고
    • Differential expression of peroxisome proliferator-activated receptors (PPARs): Tissue distribution of PPAR-alpha, -beta, and -gamma in the adult rat
    • Braissant, O.; Foufelle, F.; Scotto, C.; Dauca, M.; Wahli, W. Differential expression of peroxisome proliferator-activated receptors (PPARs): tissue distribution of PPAR-alpha, -beta, and -gamma in the adult rat Endocrinology. 1996, 137, 354-366
    • (1996) Endocrinology. , vol.137 , pp. 354-366
    • Braissant, O.1    Foufelle, F.2    Scotto, C.3    Dauca, M.4    Wahli, W.5
  • 4
    • 0030759196 scopus 로고    scopus 로고
    • PPAR gamma and the control of adipogenesis
    • Spiegelman, B. M.; Hu, E.; Kim, J. B.; Brun, R. PPAR gamma and the control of adipogenesis Biochimie 1997, 79, 111-112
    • (1997) Biochimie , vol.79 , pp. 111-112
    • Spiegelman, B.M.1    Hu, E.2    Kim, J.B.3    Brun, R.4
  • 6
    • 0141928147 scopus 로고    scopus 로고
    • PPARgamma inhibition of cyclooxygenase-2, PGE2 synthase, and inducible nitric oxide synthase in cardiac myocytes
    • Mendez, M.; LaPointe, M. C. PPARgamma inhibition of cyclooxygenase-2, PGE2 synthase, and inducible nitric oxide synthase in cardiac myocytes Hypertension 2003, 42, 844-850
    • (2003) Hypertension , vol.42 , pp. 844-850
    • Mendez, M.1    Lapointe, M.C.2
  • 7
    • 0033546003 scopus 로고    scopus 로고
    • Role of PPARgamma in regulating a cascade expression of cyclin-dependent kinase inhibitors, p18(INK4c) and p21(Waf1/Cip1), during adipogenesis
    • Morrison, R. F.; Farmer, S. R. Role of PPARgamma in regulating a cascade expression of cyclin-dependent kinase inhibitors, p18(INK4c) and p21(Waf1/Cip1), during adipogenesis J. Biol. Chem. 1999, 274, 17088-17097
    • (1999) J. Biol. Chem. , vol.274 , pp. 17088-17097
    • Morrison, R.F.1    Farmer, S.R.2
  • 10
    • 18944385230 scopus 로고    scopus 로고
    • Peroxisome proliferator activated receptor ligands and angiogenesis
    • Sato, M. Peroxisome proliferator activated receptor ligands and angiogenesis Nippon Rinsho 2005, 63, 603-608
    • (2005) Nippon Rinsho , vol.63 , pp. 603-608
    • Sato, M.1
  • 11
    • 0029016829 scopus 로고
    • An antidiabetic thiazolidinedione is a high affinity ligand for peroxisome proliferator-activated receptor gamma (PPAR gamma)
    • Lehmann, J. M.; Moore, L. B.; Smith-Oliver, T. A.; Wilkison, W. O.; Willson, T. M.; Kliewer, S. A. An antidiabetic thiazolidinedione is a high affinity ligand for peroxisome proliferator-activated receptor gamma (PPAR gamma) J. Biol. Chem. 1995, 270, 12953-12956
    • (1995) J. Biol. Chem. , vol.270 , pp. 12953-12956
    • Lehmann, J.M.1    Moore, L.B.2    Smith-Oliver, T.A.3    Wilkison, W.O.4    Willson, T.M.5    Kliewer, S.A.6
  • 12
    • 22844440938 scopus 로고    scopus 로고
    • Nuclear receptor antagonists designed based on the helix-folding inhibition hypothesis
    • Hashimoto, Y.; Miyachi, H. Nuclear receptor antagonists designed based on the helix-folding inhibition hypothesis Bioorg. Med. Chem. 2005, 13, 5080-5093
    • (2005) Bioorg. Med. Chem. , vol.13 , pp. 5080-5093
    • Hashimoto, Y.1    Miyachi, H.2
  • 13
    • 0042732947 scopus 로고    scopus 로고
    • Design, synthesis and evaluation of substituted phenylpropanoic acid derivatives as human peroxisome proliferator-activated receptor activators; Discovery of potent and human PPARα subtype-selective activators
    • Nomura, M.; Tanase, T.; Ide, T.; Tsunoda, M.; Suzuki, M.; Uchiki, H.; Murakami, K.; Miyachi, H. Design, synthesis and evaluation of substituted phenylpropanoic acid derivatives as human peroxisome proliferator-activated receptor activators; discovery of potent and human PPARα subtype-selective activators J. Med. Chem. 2003, 46, 3581-3599
    • (2003) J. Med. Chem. , vol.46 , pp. 3581-3599
    • Nomura, M.1    Tanase, T.2    Ide, T.3    Tsunoda, M.4    Suzuki, M.5    Uchiki, H.6    Murakami, K.7    Miyachi, H.8
  • 14
    • 33751065860 scopus 로고    scopus 로고
    • Design, synthesis and evaluation of a novel series of α-substituted phenylpropanoic acid derivatives as human peroxisome proliferator-activated receptor (PPAR) alpha/delta dual agonists for the treatment of metabolic syndrome
    • Kasuga, J.; Yamasaki, D.; Araya, Y.; Nakagawa, A.; Makishima, M.; Doi, T.; Hashimoto, Y.; Miyachi, H. Design, synthesis and evaluation of a novel series of α-substituted phenylpropanoic acid derivatives as human peroxisome proliferator-activated receptor (PPAR) alpha/delta dual agonists for the treatment of metabolic syndrome Bioorg. Med. Chem. 2006, 14, 8405-8414
    • (2006) Bioorg. Med. Chem. , vol.14 , pp. 8405-8414
    • Kasuga, J.1    Yamasaki, D.2    Araya, Y.3    Nakagawa, A.4    Makishima, M.5    Doi, T.6    Hashimoto, Y.7    Miyachi, H.8
  • 16
    • 38849125598 scopus 로고    scopus 로고
    • SAR-oriented discovery of peroxisome proliferator-activated receptor pan agonist with a 4-adamantylphenyl group as a hydrophobic tail
    • Kasuga, J.; Yamasaki, D.; Ogura, K.; Shimizu, M.; Sato, M.; Makishima, M.; Doi, T.; Hashimoto, Y.; Miyachi, H. SAR-oriented discovery of peroxisome proliferator-activated receptor pan agonist with a 4-adamantylphenyl group as a hydrophobic tail Bioorg. Med. Chem. Lett. 2008, 18, 1110-1105
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 1110-1105
    • Kasuga, J.1    Yamasaki, D.2    Ogura, K.3    Shimizu, M.4    Sato, M.5    Makishima, M.6    Doi, T.7    Hashimoto, Y.8    Miyachi, H.9
  • 18
    • 33845554892 scopus 로고
    • Asymmetric alkylation reactions of chiral imide enolates. A practical approach to the enantioselective synthesis of alpha-substituted carboxylic acid derivatives
    • Evans, D. A.; Ennis, M. D.; Mathre, D. J. Asymmetric alkylation reactions of chiral imide enolates. A practical approach to the enantioselective synthesis of alpha-substituted carboxylic acid derivatives J. Am. Chem. Soc. 1982, 104, 1737-1739
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 1737-1739
    • Evans, D.A.1    Ennis, M.D.2    Mathre, D.J.3
  • 19
    • 78651110586 scopus 로고    scopus 로고
    • The enantiomeric excess was determined with a CHIRALPAK AD-H column, with hexane/ i -PrOH/trifluoroacetic acid = 90:10:0.1 v/v/v as the mobile phase, at a flow rate of 0.5 mL/min, with detection at 254 nm
    • The enantiomeric excess was determined with a CHIRALPAK AD-H column, with hexane/ i -PrOH/trifluoroacetic acid = 90:10:0.1 v/v/v as the mobile phase, at a flow rate of 0.5 mL/min, with detection at 254 nm.
  • 22
    • 0029793540 scopus 로고    scopus 로고
    • Hypoglycemic activity of a series of alpha-alkylthio and alpha-alkoxy carboxylic acids related to ciglitazone
    • Hulin, B.; Newton, L. S.; Lewis, D. M.; Genereux, P. E.; Gibbs, E. M.; Clark, D. A. Hypoglycemic activity of a series of alpha-alkylthio and alpha-alkoxy carboxylic acids related to ciglitazone J. Med. Chem. 1996, 39, 3897-3907
    • (1996) J. Med. Chem. , vol.39 , pp. 3897-3907
    • Hulin, B.1    Newton, L.S.2    Lewis, D.M.3    Genereux, P.E.4    Gibbs, E.M.5    Clark, D.A.6
  • 24
    • 78651070613 scopus 로고    scopus 로고
    • Computer-graphic work was performed using MOE (Molecular Operating Environment) (Ryoka Systems Inc.)
    • Computer-graphic work was performed using MOE (Molecular Operating Environment) (Ryoka Systems Inc.).
  • 26
    • 33744792310 scopus 로고    scopus 로고
    • Sensors and signals: A coactivator/corepressor/epigenetic code for integrating signal-dependent programs of transcriptional response
    • Rosenfeld, M. G.; Lunyak, V. V.; Glass, C. K. Sensors and signals: a coactivator/corepressor/epigenetic code for integrating signal-dependent programs of transcriptional response Genes Dev. 2006, 20, 1405-1428
    • (2006) Genes Dev. , vol.20 , pp. 1405-1428
    • Rosenfeld, M.G.1    Lunyak, V.V.2    Glass, C.K.3
  • 28
    • 33745052970 scopus 로고
    • Interpretation of experiments on metabolic processes, using isotopic tracer elements
    • Ogston, A. G. Interpretation of experiments on metabolic processes, using isotopic tracer elements Nature 1948, 163, 963
    • (1948) Nature , vol.163 , pp. 963
    • Ogston, A.G.1
  • 29
    • 0000165020 scopus 로고
    • Studies on the relationship between chemical constitution and physiological action-Molecular dissymmetry and physiological activity
    • Easson, L. H.; Stedman, E. Studies on the relationship between chemical constitution and physiological action-Molecular dissymmetry and physiological activity Biochem. J. 1933, 27, 1257-1266
    • (1933) Biochem. J. , vol.27 , pp. 1257-1266
    • Easson, L.H.1    Stedman, E.2
  • 30
    • 57849098033 scopus 로고    scopus 로고
    • Structural insight into PPARgamma activation through covalent modification with endogenous fatty acids
    • Waku, T.; Shiraki, T.; Oyama, T.; Fujimoto, Y.; Maebara, K.; Kamiya, N.; Jingami, H.; Morikawa, K. Structural insight into PPARgamma activation through covalent modification with endogenous fatty acids J. Mol. Biol. 2009, 385, 188-199
    • (2009) J. Mol. Biol. , vol.385 , pp. 188-199
    • Waku, T.1    Shiraki, T.2    Oyama, T.3    Fujimoto, Y.4    Maebara, K.5    Kamiya, N.6    Jingami, H.7    Morikawa, K.8
  • 33
    • 84889120137 scopus 로고
    • Improved methods for building protein models in electron density maps and the location of errors in these models
    • Jones, T. A.; Zou, J.-Y.; Cowan, S. W.; Kjeldgaard, M. Improved methods for building protein models in electron density maps and the location of errors in these models Acta Crystallogr. 1991, A47, 110-119
    • (1991) Acta Crystallogr. , vol.47 , pp. 110-119
    • Jones, T.A.1    Zou, J.-Y.2    Cowan, S.W.3    Kjeldgaard, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.