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Volumn 52, Issue 20, 2009, Pages 6224-6232

Synthesis and biological evaluation of 2-heteroarylthioalkanoic acid analogues of clofibric acid as peroxisome proliferator-activated receptor α agonists

Author keywords

[No Author keywords available]

Indexed keywords

2 [4 [2 [3 CYCLOHEXYL 1 (4 CYCLOHEXYLBUTYL)UREIDO]ETHYL]PHENYLTHIO] 2 METHYLPROPIONIC ACID; 2 [4 [3 [4,5 DIHYDRO 1 (4 METHYLBENZYL) 5 OXO 1H 1,2,4 TRIAZOL 3 YL]PROPYL]PHENOXY] 2 METHYLPROPIONIC ACID; 2 HETEROARYLTHIOALKANOIC ACID DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; CLOFIBRIC ACID; KCL 1998001079; NS 220; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA AGONIST; THIOPHENE; UNCLASSIFIED DRUG;

EID: 70350061743     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900878u     Document Type: Article
Times cited : (24)

References (43)
  • 1
    • 0025132245 scopus 로고
    • Activation of a member of the steroid hormone receptor superfamily by peroxisome proliferators
    • DOI 10.1038/347645a0
    • (a) Issemann, I.; Green, S. Activation of a member of the steroid hormone receptor superfamily by peroxisome proliferators. Nature 1990, 347, 645-650. (Pubitemid 20356241)
    • (1990) Nature , vol.347 , Issue.6294 , pp. 645-650
    • Issemann, I.1    Green, S.2
  • 2
    • 0027738795 scopus 로고
    • Peroxisome proliferator-activated receptor (PPAR): Structure, mechanisms of activation and diverse functions
    • (b) Motojima, K. Peroxisome proliferator-activated receptor (PPAR): structure, mechanisms of activation and diverse functions. Cell Struct. Funct. 1993, 18, 267-277.
    • (1993) Cell Struct. Funct. , vol.18 , pp. 267-277
    • Motojima, K.1
  • 3
    • 34547661571 scopus 로고    scopus 로고
    • Peroxisome proliferator-activated receptor structures: Ligand specificity, molecular switch and interactions with regulators
    • (c) Zoete, V.; Grosdidier, A.; Michielin, O. Peroxisome proliferator-activated receptor structures: ligand specificity, molecular switch and interactions with regulators. Biochim. Biophys. Acta 2007, 1771, 915-925.
    • (2007) Biochim. Biophys. Acta , vol.1771 , pp. 915-925
    • Zoete, V.1    Grosdidier, A.2    Michielin, O.3
  • 5
    • 0036183630 scopus 로고    scopus 로고
    • The mechanisms of action of PPARs
    • (a) Berger, J.; Moller, D. E. The mechanisms of action of PPARs. Annu. Rev. Med. 2002, 53, 409-435.
    • (2002) Annu. Rev. Med. , vol.53 , pp. 409-435
    • Berger, J.1    Moller, D.E.2
  • 7
    • 32644460092 scopus 로고    scopus 로고
    • From molecular action to physiological outputs: Peroxisome proliferator-activated receptors are nuclear receptors at the crossroads of key cellular functions
    • (c) Feige, J. N.; Gelman, L.; Michalik, L.; Desvergne, B.; Wahli, W. From molecular action to physiological outputs: peroxisome proliferator-activated receptors are nuclear receptors at the crossroads of key cellular functions. Prog. Lipid Res. 2006, 45, 120-159.
    • (2006) Prog. Lipid Res. , vol.45 , pp. 120-159
    • Feige, J.N.1    Gelman, L.2    Michalik, L.3    Desvergne, B.4    Wahli, W.5
  • 8
    • 0030952937 scopus 로고    scopus 로고
    • Hypolipidemic drugs, polyunsaturated fatty acids, and eicosanoids are ligands for peroxisome proliferator-activated receptors α and δ
    • (a) Forman, B. M.; Chen, J.; Evans, R. M. Hypolipidemic drugs, polyunsaturated fatty acids, and eicosanoids are ligands for peroxisome proliferator-activated receptors α and δ. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 4312-4317.
    • (1997) Proc. Natl. Acad. Sci. U.S.A. , vol.94 , pp. 4312-4317
    • Forman, B.M.1    Chen, J.2    Evans, R.M.3
  • 10
    • 0037389926 scopus 로고    scopus 로고
    • Peroxisome proliferator-activated receptors: A critical review on endogenous pathways for ligand generation
    • DOI 10.1016/S0090-6980(03)00003-0
    • (c) Bishop-Bailey, D.; Wray, J. Peroxisome proliferator-activated receptors: a critical review on endogenous pathways for ligand generation. Prostaglandins Other Lipid Mediators 2003, 71, 1-22. (Pubitemid 36428519)
    • (2003) Prostaglandins and Other Lipid Mediators , vol.71 , Issue.1-2 , pp. 1-22
    • Bishop-Bailey, D.1    Wray, J.2
  • 11
    • 35648942191 scopus 로고    scopus 로고
    • Peroxisome proliferator-activated receptors as sensors of fatty acids and derivatives
    • (d) Grimaldi, P. A. Peroxisome proliferator-activated receptors as sensors of fatty acids and derivatives. Cell. Mol. Life Sci. 2007, 64, 2459-2464.
    • (2007) Cell. Mol. Life Sci. , vol.64 , pp. 2459-2464
    • Grimaldi, P.A.1
  • 12
    • 21644436821 scopus 로고    scopus 로고
    • Peroxisome proliferator-activated receptor (PPAR)-α: A pharmacological target with a promising future
    • (a) van Raalte, D. H.; Li, M.; Pritchard, P. H.; Wasan, K. M. Peroxisome proliferator-activated receptor (PPAR)-α: a pharmacological target with a promising future. Pharm. Res. 2004, 21, 1531.
    • (2004) Pharm. Res. , vol.21 , pp. 1531
    • Van Raalte, D.H.1    Li, M.2    Pritchard, P.H.3    Wasan, K.M.4
  • 13
    • 33644652183 scopus 로고    scopus 로고
    • Sorting out the roles of PPARα in energy metabolism and vascular homeostasis
    • (b) Lefebvre, P.; Chinetti, G.; Fruchart, J. C.; Bart Staels, B. Sorting out the roles of PPARα in energy metabolism and vascular homeostasis. J. Clin. Invest. 2006, 116, 571-580.
    • (2006) J. Clin. Invest. , vol.116 , pp. 571-580
    • Lefebvre, P.1    Chinetti, G.2    Fruchart, J.C.3    Bart Staels, B.4
  • 15
    • 23944451559 scopus 로고    scopus 로고
    • Peroxisome proliferator-activated receptor-alpha and atherosclerosis: From basic mechanisms to clinical implications
    • (b) Israelian-Konaraki, Z.; Reaven, P. D. Peroxisome proliferator- activated receptor-alpha and atherosclerosis: from basic mechanisms to clinical implications. Cardiol. Rev. 2005, 13, 240-246.
    • (2005) Cardiol. Rev. , vol.13 , pp. 240-246
    • Israelian-Konaraki, Z.1    Reaven, P.D.2
  • 18
    • 50249168289 scopus 로고    scopus 로고
    • PPAR-α: Therapeutic role in diabetes-related cardiovascular disease
    • (e) Cheng, A. Y. Y.; Leiter, L. A. PPAR-α: therapeutic role in diabetes-related cardiovascular disease. Diabetes, Obes. Metab. 2008, 9, 691-698.
    • (2008) Diabetes, Obes. Metab. , vol.9 , pp. 691-698
    • Cheng, A.Y.Y.1    Leiter, L.A.2
  • 19
    • 2542623014 scopus 로고    scopus 로고
    • Synthetic ligands for peroxisome proliferator-activated receptor-α, review of the patent literature 2000-2003
    • (a) Miyachi, H. Synthetic ligands for peroxisome proliferator-activated receptor-α, review of the patent literature 2000-2003. Expert Opin. Ther. Pat. 2004, 14, 607-618.
    • (2004) Expert Opin. Ther. Pat. , vol.14 , pp. 607-618
    • Miyachi, H.1
  • 20
    • 34347333419 scopus 로고    scopus 로고
    • PPAR ligands: Are they potential agents for cardiovascular disorders?
    • (b) Balakumar, P.; Rose, M.; Singh, M. PPAR ligands: are they potential agents for cardiovascular disorders? Pharmacology 2007, 80, 1-10.
    • (2007) Pharmacology , vol.80 , pp. 1-10
    • Balakumar, P.1    Rose, M.2    Singh, M.3
  • 21
    • 36349013615 scopus 로고    scopus 로고
    • Novel peroxisome proliferator activated receptor-α agonists
    • (c) Fruchart, J. C. Novel peroxisome proliferator activated receptor-α agonists. Am. J. Cardiol. 2007, 100, 41-46.
    • (2007) Am. J. Cardiol. , vol.100 , pp. 41-46
    • Fruchart, J.C.1
  • 22
    • 0029994543 scopus 로고    scopus 로고
    • Role of the peroxisome proliferator-activated receptor (PPAR) in mediating the effects of fibrates and fatty acids on gene expression
    • (a) Schoonjans, K.; Staels, B. M; Auwerx, J. Role of the peroxisome proliferator-activated receptor (PPAR) in mediating the effects of fibrates and fatty acids on gene expression. J. Lipid Res. 1996, 37, 907-925. (Pubitemid 26182326)
    • (1996) Journal of Lipid Research , vol.37 , Issue.5 , pp. 907-925
    • Schoonjans, K.1    Staels, B.2    Auwerx, J.3
  • 23
    • 0031008797 scopus 로고    scopus 로고
    • Role of PPAR in the pharmacological regulation of lipoprotein metabolism by fibrates and thiazolidinediones
    • (b) Staels, B.; Auwerx, J. Role of PPAR in the pharmacological regulation of lipoprotein metabolism by fibrates and thiazolidinediones. Curr. Pharm. Des. 1997, 3, 1-14.
    • (1997) Curr. Pharm. Des. , vol.3 , pp. 1-14
    • Staels, B.1    Auwerx, J.2
  • 24
    • 17344376201 scopus 로고    scopus 로고
    • Molecular mechanism of action of the fibrates
    • (c) Fruchart, J. C.; Duriez, P.; Staels, B. Molecular mechanism of action of the fibrates. J. Soc. Biol. 1999, 193, 67-75.
    • (1999) J. Soc. Biol. , vol.193 , pp. 67-75
    • Fruchart, J.C.1    Duriez, P.2    Staels, B.3
  • 25
    • 0344874601 scopus 로고    scopus 로고
    • Fibrates in 2003: Therapeutic action in atherogenic dyslipidaemia and future perspectives
    • (d) Chapman, M. J. Fibrates in 2003: therapeutic action in atherogenic dyslipidaemia and future perspectives. Atherosclerosis 2003, 171, 1-13.
    • (2003) Atherosclerosis , vol.171 , pp. 1-13
    • Chapman, M.J.1
  • 27
    • 37549041988 scopus 로고    scopus 로고
    • Is there a role for fibrates in the management of dyslipidemia in the metabolic syndrome?
    • (f) Barter, P. J.; Rye, K.-A. Is there a role for fibrates in the management of dyslipidemia in the metabolic syndrome? Arterioscler., Thromb., Vasc. Biol. 2008, 28, 39-46.
    • (2008) Arterioscler., Thromb., Vasc. Biol. , vol.28 , pp. 39-46
    • Barter, P.J.1    Rye, K.-A.2
  • 28
    • 50649089597 scopus 로고    scopus 로고
    • Fibrates and future PPARα agonists in the treatment of cardiovascular disease
    • (g) Staels, B.; Maes, M.; Zambon, A. Fibrates and future PPARα agonists in the treatment of cardiovascular disease. Nat. Clin. Pract. Cardiovasc. Med. 2008, 5, 542-553.
    • (2008) Nat. Clin. Pract. Cardiovasc. Med. , vol.5 , pp. 542-553
    • Staels, B.1    Maes, M.2    Zambon, A.3
  • 30
    • 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 peroxisome proliferator activated receptor α subtype-selective activators
    • (a) 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 peroxisome proliferator activated receptor α 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
  • 35
    • 38549092684 scopus 로고    scopus 로고
    • Structure-activity studies on 1,3-dioxane-2-carboxylic acid derivatives, a novel class of subtype-selective peroxisome proliferator-activated receptor α (PPARα) agonists
    • DOI 10.1016/j.bmc.2007.10.007, PII S0968089607008528
    • (a) Asaki, T.; Aoki, T.; Hamamoto, T.; Sugiyama, Y.; Ohmachi, S.; Kuwabara, K.; Murakami, K; Todo, M. Structure-activity studies on 1,3-dioxane-2-carboxylic acid derivatives, a novel class of subtype-selective peroxisome proliferator-activated receptor α (PPARα) agonists. Bioorg. Med. Chem. 2008, 16, 981-994. (Pubitemid 351163042)
    • (2008) Bioorganic and Medicinal Chemistry , vol.16 , Issue.2 , pp. 981-994
    • Asaki, T.1    Aoki, T.2    Hamamoto, T.3    Sugiyama, Y.4    Ohmachi, S.5    Kuwabara, K.6    Murakami, K.7    Todo, M.8
  • 36
    • 40749118856 scopus 로고    scopus 로고
    • Discovery of a novel class of 1,3-dioxane-2-carboxylic acid derivatives as subtype-selective peroxisome proliferator-activated receptor α (PPARα) agonists
    • (b) Aoki, T.; Asaki, T.; Hamamoto, T.; Sugiyama, Y.; Ohmachi, S.; Kuwabara, K.; Murakami, K; Todo, M. Discovery of a novel class of 1,3-dioxane-2-carboxylic acid derivatives as subtype-selective peroxisome proliferator-activated receptor α (PPARα) agonists. Bioorg. Med. Chem. Lett. 2008, 18, 2128-2132.
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 2128-2132
    • Aoki, T.1    Asaki, T.2    Hamamoto, T.3    Sugiyama, Y.4    Ohmachi, S.5    Kuwabara, K.6    Murakami, K.7    Todo, M.8
  • 38
    • 19644388300 scopus 로고    scopus 로고
    • A convenient synthesis of 2-mercapto and 2-chlorobenzothiazoles
    • Zhu, L.; Zhang, M.; Dai, M. A convenient synthesis of 2-mercapto and 2-chlorobenzothiazoles. J.Heterocycl.Chem. 2005, 42, 727-730.
    • (2005) J.Heterocycl.Chem. , vol.42 , pp. 727-730
    • Zhu, L.1    Zhang, M.2    Dai, M.3
  • 39
    • 2642551635 scopus 로고    scopus 로고
    • The flip side: Identifying small molecule regulators of nuclear receptors
    • Schulman, I. G.; Heyman, R. A. The flip side: identifying small molecule regulators of nuclear receptors. Chem.Biol. 2004, 11, 639-646.
    • (2004) Chem.Biol. , vol.11 , pp. 639-646
    • Schulman, I.G.1    Heyman, R.A.2
  • 40
    • 0030890262 scopus 로고    scopus 로고
    • Stereoselective effects of chiral clofibric acid analogs on rat peroxisome proliferator-activated receptor (rPPAR) activation and peroxisomal fatty acid-oxidation
    • Rangwala, S. M.; O'Brien, M. L.; Tortorella, V.; Longo, A.; Loiodice, F.; Noonan, D. J.; Feller, D. R. Stereoselective effects of chiral clofibric acid analogs on rat peroxisome proliferator-activated receptor (rPPAR) activation and peroxisomal fatty acid-oxidation. Chirality 1997, 9, 37-47.
    • (1997) Chirality , vol.9 , pp. 37-47
    • Rangwala, S.M.1    O'Brien, M.L.2    Tortorella, V.3    Longo, A.4    Loiodice, F.5    Noonan, D.J.6    Feller, D.R.7
  • 41
    • 34848833429 scopus 로고    scopus 로고
    • Synthesis, biological evaluation, and molecular modeling investigation of chiral phenoxyacetic acid analogues with PPARα and PPARγ agonist activity
    • Fracchiolla, G; Laghezza, A.; Piemontese, L.; Carbonara, G.; Lavecchia, A.; Tortorella, P.; Crestani, M.;Novellino, E.; Loiodice, F. Synthesis, biological evaluation, and molecular modeling investigation of chiral phenoxyacetic acid analogues with PPARα and PPARγ agonist activity. ChemMedChem 2007, 14, 641-654.
    • (2007) ChemMedChem , vol.14 , pp. 641-654
    • Fracchiolla, G.1    Laghezza, A.2    Piemontese, L.3    Carbonara, G.4    Lavecchia, A.5    Tortorella, P.6    Crestani, M.7    Novellino, E.8    Loiodice, F.9
  • 42
    • 0037059928 scopus 로고    scopus 로고
    • Enantio-dependent binding and transactivation of optically active phenylpropanoic acid derivatives at human peroxisome proliferator-activated receptor alpha
    • Miyachi, H.; Nomura, M.; Tanase, T.; Suzuki, M.; Murakami, K.; Awano, K. Enantio-dependent binding and transactivation of optically active phenylpropanoic acid derivatives at human peroxisome proliferator-activated receptor alpha. Bioorg. Med. Chem. Lett. 2002, 12, 333-335.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 333-335
    • Miyachi, H.1    Nomura, M.2    Tanase, T.3    Suzuki, M.4    Murakami, K.5    Awano, K.6
  • 43
    • 0035943681 scopus 로고    scopus 로고
    • Differential gene regulation in human versus rodent hepatocytes by peroxisome proliferator-activated receptor (PPAR) alpha. PPAR alpha fails to induce peroxisome proliferation-associated genes in human cells independently of the level of receptor expression
    • Lawrence, J. W.; Li, Y.; Chen, S.; De Luca, J. G.; Berger, J. P.; Umbenhauer, D. R.; Moller, D. E.; Zhou, G. Differential gene regulation in human versus rodent hepatocytes by peroxisome proliferator-activated receptor (PPAR) alpha. PPAR alpha fails to induce peroxisome proliferation-associated genes in human cells independently of the level of receptor expression. J. Biol. Chem. 2001, 276, 31521-31527.
    • (2001) J. Biol. Chem. , vol.276 , pp. 31521-31527
    • Lawrence, J.W.1    Li, Y.2    Chen, S.3    De Luca, J.G.4    Berger, J.P.5    Umbenhauer, D.R.6    Moller, D.E.7    Zhou, G.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.