메뉴 건너뛰기




Volumn 113, Issue , 2016, Pages 246-257

Design, synthesis and Structure-activity relationship studies of new thiazole-based free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

Author keywords

Dihedral angle; FFA1 agonist; GPR40; Heteroaromatics; Liver toxicity; Type 2 diabetes

Indexed keywords

ALANINE AMINOTRANSFERASE; ANTIDIABETIC AGENT; ASPARTATE AMINOTRANSFERASE; BILIRUBIN; FASIGLIFAM; G PROTEIN COUPLED RECEPTOR 40; GLIBENCLAMIDE; GLUCOSE; THIAZOLE DERIVATIVE; G PROTEIN COUPLED RECEPTOR; GLUCOSE BLOOD LEVEL;

EID: 84959362883     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2016.02.040     Document Type: Article
Times cited : (52)

References (54)
  • 1
    • 64649104158 scopus 로고    scopus 로고
    • From the triumvirate to the ominous octet: a new paradigm for the treatment of type 2 diabetes mellitus
    • R.A. DeFronzo From the triumvirate to the ominous octet: a new paradigm for the treatment of type 2 diabetes mellitus Diabetes 58 2009 773 795
    • (2009) Diabetes , vol.58 , pp. 773-795
    • DeFronzo, R.A.1
  • 2
    • 79959936188 scopus 로고    scopus 로고
    • C Global Burden Metab Risk Factors, National, regional, and global trends in fasting plasma glucose and diabetes prevalence since 1980: systematic analysis of health examination surveys and epidemiological studies with 370 country-years and 2.7 million participants
    • G. Danaei, M.M. Finucane, Y. Lu, G.M. Singh, M.J. Cowan, C.J. Paciorek, J.K. Lin, F. Farzadfar, Y.-H. Khang, G.A. Stevens, M. Rao, M.K. Ali, L.M. Riley, C.A. Robinson, M. Ezzati, and C Global Burden Metab Risk Factors National, regional, and global trends in fasting plasma glucose and diabetes prevalence since 1980: systematic analysis of health examination surveys and epidemiological studies with 370 country-years and 2.7 million participants Lancet 378 2011 31 40
    • (2011) Lancet , vol.378 , pp. 31-40
    • Danaei, G.1    Finucane, M.M.2    Lu, Y.3    Singh, G.M.4    Cowan, M.J.5    Paciorek, C.J.6    Lin, J.K.7    Farzadfar, F.8    Khang, Y.-H.9    Stevens, G.A.10    Rao, M.11    Ali, M.K.12    Riley, L.M.13    Robinson, C.A.14    Ezzati, M.15
  • 3
    • 77950891085 scopus 로고    scopus 로고
    • Effect of noninsulin antidiabetic drugs added to metformin therapy on glycemic control, weight gain, and hypoglycemia in type 2 diabetes
    • O.J. Phung, J.M. Scholle, M. Talwar, and C.I. Coleman Effect of noninsulin antidiabetic drugs added to metformin therapy on glycemic control, weight gain, and hypoglycemia in type 2 diabetes JAMA 303 2010 1410 1418
    • (2010) JAMA , vol.303 , pp. 1410-1418
    • Phung, O.J.1    Scholle, J.M.2    Talwar, M.3    Coleman, C.I.4
  • 5
    • 84874184400 scopus 로고    scopus 로고
    • A review of the efficacy and safety of oral antidiabetic drugs
    • S.A. Stein, E.M. Lamos, and S.N. Davis A review of the efficacy and safety of oral antidiabetic drugs Expert Opin. Drug Saf. 12 2013 153 175
    • (2013) Expert Opin. Drug Saf. , vol.12 , pp. 153-175
    • Stein, S.A.1    Lamos, E.M.2    Davis, S.N.3
  • 6
    • 79959601676 scopus 로고    scopus 로고
    • Type 2 diabetes mellitus-current therapies and the emergence of surgical options
    • H.E. Lebovitz Type 2 diabetes mellitus-current therapies and the emergence of surgical options Nat. Rev. Endocrinol. 7 2011 408 419
    • (2011) Nat. Rev. Endocrinol. , vol.7 , pp. 408-419
    • Lebovitz, H.E.1
  • 7
    • 79960262492 scopus 로고    scopus 로고
    • Management of type 2 diabetes: new and future developments in treatment
    • A.A. Tahrani, C.J. Bailey, S. Del Prato, and A.H. Barnett Management of type 2 diabetes: new and future developments in treatment Lancet 378 2011 182 197
    • (2011) Lancet , vol.378 , pp. 182-197
    • Tahrani, A.A.1    Bailey, C.J.2    Del Prato, S.3    Barnett, A.H.4
  • 8
    • 84906342905 scopus 로고    scopus 로고
    • Novel approaches to drug discovery for the treatment of type 2 diabetes
    • X. Xu, G. Wang, T. Zhou, L. Chen, J. Chen, and X. Shen Novel approaches to drug discovery for the treatment of type 2 diabetes Expert Opin. Drug Dis. 9 2014 1047 1058
    • (2014) Expert Opin. Drug Dis. , vol.9 , pp. 1047-1058
    • Xu, X.1    Wang, G.2    Zhou, T.3    Chen, L.4    Chen, J.5    Shen, X.6
  • 11
    • 58149095589 scopus 로고    scopus 로고
    • International union of pharmacology. LXXI. Free fatty acid receptors FFA1,-2, and-3: pharmacology and pathophysiological functions
    • L.A. Stoddart, N.J. Smith, and G. Milligan International union of pharmacology. LXXI. Free fatty acid receptors FFA1,-2, and-3: pharmacology and pathophysiological functions Pharmacol. Rev. 60 2008 405 417
    • (2008) Pharmacol. Rev. , vol.60 , pp. 405-417
    • Stoddart, L.A.1    Smith, N.J.2    Milligan, G.3
  • 12
    • 69549111756 scopus 로고    scopus 로고
    • Molecular pharmacology of promiscuous seven transmembrane receptors sensing organic nutrients
    • P. Wellendorph, L.D. Johansen, and H. Bräuner-Osborne Molecular pharmacology of promiscuous seven transmembrane receptors sensing organic nutrients Mol. Pharmacol. 76 2009 453 465
    • (2009) Mol. Pharmacol. , vol.76 , pp. 453-465
    • Wellendorph, P.1    Johansen, L.D.2    Bräuner-Osborne, H.3
  • 23
    • 84902546389 scopus 로고    scopus 로고
    • Recent developments in the discovery of FFA1 receptor agonists as novel oral treatment for type 2 diabetes mellitus
    • E. Defossa, and M. Wagner Recent developments in the discovery of FFA1 receptor agonists as novel oral treatment for type 2 diabetes mellitus Bioorg. Med. Chem. Lett. 24 2014 2991 3000
    • (2014) Bioorg. Med. Chem. Lett. , vol.24 , pp. 2991-3000
    • Defossa, E.1    Wagner, M.2
  • 24
    • 84870249445 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Deliv. Rev. 64 2012 4 17
    • (2012) Adv. Drug Deliv. Rev. , vol.64 , pp. 4-17
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 26
    • 77749315417 scopus 로고    scopus 로고
    • Lipophilicity in drug discovery
    • M.J. Waring Lipophilicity in drug discovery Expert Opin. Drug Dis. 5 2010 235 248
    • (2010) Expert Opin. Drug Dis. , vol.5 , pp. 235-248
    • Waring, M.J.1
  • 27
    • 61649109015 scopus 로고    scopus 로고
    • The influence of lead discovery strategies on the properties of drug candidates
    • G.M. Keserü, and G.M. Makara The influence of lead discovery strategies on the properties of drug candidates Nat. Rev. Drug Discov. 8 2009 203 212
    • (2009) Nat. Rev. Drug Discov. , vol.8 , pp. 203-212
    • Keserü, G.M.1    Makara, G.M.2
  • 28
    • 84938495908 scopus 로고    scopus 로고
    • Molecular property design: does everyone get it?
    • P.D. Leeson, and R.J. Young Molecular property design: does everyone get it? ACS Med. Chem. Lett. 6 2015 722 725
    • (2015) ACS Med. Chem. Lett. , vol.6 , pp. 722-725
    • Leeson, P.D.1    Young, R.J.2
  • 29
    • 39749181550 scopus 로고    scopus 로고
    • Generation of a set of simple, interpretable ADMET rules of thumb
    • M.P. Gleeson Generation of a set of simple, interpretable ADMET rules of thumb J. Med. Chem. 51 2008 817 834
    • (2008) J. Med. Chem. , vol.51 , pp. 817-834
    • Gleeson, M.P.1
  • 30
    • 79955419410 scopus 로고    scopus 로고
    • Synopsis of some recent tactical application of bioisosteres in drug design
    • N.A. Meanwell Synopsis of some recent tactical application of bioisosteres in drug design J. Med. Chem. 54 2011 2529 2591
    • (2011) J. Med. Chem. , vol.54 , pp. 2529-2591
    • Meanwell, N.A.1
  • 31
    • 80052974259 scopus 로고    scopus 로고
    • Improving drug candidates by design: a focus on physicochemical properties as a means of improving compound disposition and safety
    • N.A. Meanwell Improving drug candidates by design: a focus on physicochemical properties as a means of improving compound disposition and safety Chem. Res. Toxicol. 24 2011 1420 1456
    • (2011) Chem. Res. Toxicol. , vol.24 , pp. 1420-1456
    • Meanwell, N.A.1
  • 33
    • 84859625938 scopus 로고    scopus 로고
    • TAK-875 versus placebo or glimepiride in type 2 diabetes mellitus: a phase 2, randomised, double-blind, placebo-controlled trial
    • C.F. Burant, P. Viswanathan, J. Marcinak, C. Cao, M. Vakilynejad, B. Xie, and E. Leifke TAK-875 versus placebo or glimepiride in type 2 diabetes mellitus: a phase 2, randomised, double-blind, placebo-controlled trial Lancet 379 2012 1403 1411
    • (2012) Lancet , vol.379 , pp. 1403-1411
    • Burant, C.F.1    Viswanathan, P.2    Marcinak, J.3    Cao, C.4    Vakilynejad, M.5    Xie, B.6    Leifke, E.7
  • 34
    • 84873835561 scopus 로고    scopus 로고
    • Randomized, double-blind, dose-ranging study of TAK-875, a novel GPR40 agonist, in Japanese patients with inadequately controlled type 2 diabetes
    • K. Kaku, T. Araki, and R. Yoshinaka Randomized, double-blind, dose-ranging study of TAK-875, a novel GPR40 agonist, in Japanese patients with inadequately controlled type 2 diabetes Diabetes Care 36 2013 245 250
    • (2013) Diabetes Care , vol.36 , pp. 245-250
    • Kaku, K.1    Araki, T.2    Yoshinaka, R.3
  • 36
    • 84918814911 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of phenoxyacetic acid derivatives as novel free fatty acid receptor 1 agonists
    • X. Wang, T. Zhao, B. Yang, Z. Li, J. Cui, Y. Dai, Q. Qiu, H. Qiang, W. Huang, and H. Qian Synthesis and biological evaluation of phenoxyacetic acid derivatives as novel free fatty acid receptor 1 agonists Bioorg. Med. Chem. 23 2015 132 140
    • (2015) Bioorg. Med. Chem. , vol.23 , pp. 132-140
    • Wang, X.1    Zhao, T.2    Yang, B.3    Li, Z.4    Cui, J.5    Dai, Y.6    Qiu, Q.7    Qiang, H.8    Huang, W.9    Qian, H.10
  • 37
    • 18244408269 scopus 로고    scopus 로고
    • Synthesis of [1, 2, 4] triazolo [4, 3-α] piperazines via highly reactive chloromethyloxadiazoles
    • J. Balsells, L. DiMichele, J. Liu, M. Kubryk, K. Hansen, and J.D. Armstrong Synthesis of [1, 2, 4] triazolo [4, 3-α] piperazines via highly reactive chloromethyloxadiazoles Org. Lett. 7 2005 1039 1042
    • (2005) Org. Lett. , vol.7 , pp. 1039-1042
    • Balsells, J.1    Dimichele, L.2    Liu, J.3    Kubryk, M.4    Hansen, K.5    Armstrong, J.D.6
  • 38
    • 0029899173 scopus 로고    scopus 로고
    • Synthesis, ligand binding, and quantitative structure-activity relationship study of 3β-(4′-substituted phenyl)-2β-heterocyclic tropanes: evidence for an electrostatic interaction at the 2β-position
    • P. Kotian, S.W. Mascarella, P. Abraham, A.H. Lewin, J.W. Boja, M.J. Kuhar, and F.I. Carroll Synthesis, ligand binding, and quantitative structure-activity relationship study of 3β-(4′-substituted phenyl)-2β-heterocyclic tropanes: evidence for an electrostatic interaction at the 2β-position J. Med. Chem. 39 1996 2753 2763
    • (1996) J. Med. Chem. , vol.39 , pp. 2753-2763
    • Kotian, P.1    Mascarella, S.W.2    Abraham, P.3    Lewin, A.H.4    Boja, J.W.5    Kuhar, M.J.6    Carroll, F.I.7
  • 40
    • 0037696879 scopus 로고    scopus 로고
    • New pyrazolium-carboxylates as structural analogues of the pseudo-cross-conjugated betainic alkaloid Nigellicine
    • A. Schmidt, T. Habeck, M.K. Kindermann, and M. Nieger New pyrazolium-carboxylates as structural analogues of the pseudo-cross-conjugated betainic alkaloid Nigellicine J. Org. Chem. 68 2003 5977 5982
    • (2003) J. Org. Chem. , vol.68 , pp. 5977-5982
    • Schmidt, A.1    Habeck, T.2    Kindermann, M.K.3    Nieger, M.4
  • 41
    • 0002569662 scopus 로고
    • The acylation of ketones to form β-diketones or β-keto aldehydes
    • C.R. Hauser, F.W. Swamer, and J.T. Adams The acylation of ketones to form β-diketones or β-keto aldehydes Org. React. 8 1954 59 196
    • (1954) Org. React. , vol.8 , pp. 59-196
    • Hauser, C.R.1    Swamer, F.W.2    Adams, J.T.3
  • 42
    • 0005216139 scopus 로고
    • The use of sodium methoxide in the Claisen reaction
    • E.E. Royals The use of sodium methoxide in the Claisen reaction J. Am. Chem. Soc. 67 1945 1508 1509
    • (1945) J. Am. Chem. Soc. , vol.67 , pp. 1508-1509
    • Royals, E.E.1
  • 43
    • 23744439852 scopus 로고    scopus 로고
    • Total synthesis of thiostrepton. Assembly of key building blocks and completion of the synthesis
    • K. Nicolaou, M. Zak, B.S. Safina, A.A. Estrada, S.H. Lee, and M. Nevalainen Total synthesis of thiostrepton. Assembly of key building blocks and completion of the synthesis J. Am. Chem. Soc. 127 2005 11176 11183
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 11176-11183
    • Nicolaou, K.1    Zak, M.2    Safina, B.S.3    Estrada, A.A.4    Lee, S.H.5    Nevalainen, M.6
  • 44
    • 84863230611 scopus 로고    scopus 로고
    • Synthesis and evaluation of sulfonylnitrophenylthiazoles (SNPTs) as thyroid hormone receptor-coactivator interaction inhibitors
    • J.Y. Hwang, R.R. Attia, F. Zhu, L. Yang, A. Lemoff, C. Jeffries, M.C. Connelly, and R.K. Guy Synthesis and evaluation of sulfonylnitrophenylthiazoles (SNPTs) as thyroid hormone receptor-coactivator interaction inhibitors J. Med. Chem. 55 2012 2301 2310
    • (2012) J. Med. Chem. , vol.55 , pp. 2301-2310
    • Hwang, J.Y.1    Attia, R.R.2    Zhu, F.3    Yang, L.4    Lemoff, A.5    Jeffries, C.6    Connelly, M.C.7    Guy, R.K.8
  • 45
    • 0000096835 scopus 로고    scopus 로고
    • Click chemistry: diverse chemical function from a few good reactions
    • H.C. Kolb, M. Finn, and K.B. Sharpless Click chemistry: diverse chemical function from a few good reactions Angew. Chem. Int. Ed. 40 2001 2004 2021
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2004-2021
    • Kolb, H.C.1    Finn, M.2    Sharpless, K.B.3
  • 47
    • 84863856481 scopus 로고    scopus 로고
    • Mitigating heterocycle metabolism in drug discovery
    • D.J. St. Jean Jr., and C. Fotsch Mitigating heterocycle metabolism in drug discovery J. Med. Chem. 55 2012 6002 6020
    • (2012) J. Med. Chem. , vol.55 , pp. 6002-6020
    • St. Jean, D.J.1    Fotsch, C.2
  • 48
    • 0037019551 scopus 로고    scopus 로고
    • Statistical and theoretical investigations on the directionality of nonbonded S⋯O interactions. implications for molecular design and protein engineering
    • M. Iwaoka, S. Takemoto, and S. Tomoda Statistical and theoretical investigations on the directionality of nonbonded S⋯O interactions. implications for molecular design and protein engineering J. Am. Chem. Soc. 124 2002 10613 10620
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10613-10620
    • Iwaoka, M.1    Takemoto, S.2    Tomoda, S.3
  • 51
    • 20544433165 scopus 로고
    • Van der Waals volumes and radii
    • A. Bondi van der Waals volumes and radii J. Phys. Chem. 68 1964 441 451
    • (1964) J. Phys. Chem. , vol.68 , pp. 441-451
    • Bondi, A.1
  • 53
    • 3543009434 scopus 로고    scopus 로고
    • The high-fat diet-fed mouse a model for studying mechanisms and treatment of impaired glucose tolerance and type 2 diabetes
    • M.S. Winzell, and B. Ahrén The high-fat diet-fed mouse a model for studying mechanisms and treatment of impaired glucose tolerance and type 2 diabetes Diabetes 53 2004 215 219
    • (2004) Diabetes , vol.53 , pp. 215-219
    • Winzell, M.S.1    Ahrén, B.2
  • 54
    • 70349120958 scopus 로고    scopus 로고
    • Glucagon-like peptide-1 receptor activation modulates pancreatitis-associated gene expression but does not modify the susceptibility to experimental pancreatitis in mice
    • J.A. Koehler, L.L. Baggio, B.J. Lamont, S. Ali, and D.J. Drucker Glucagon-like peptide-1 receptor activation modulates pancreatitis-associated gene expression but does not modify the susceptibility to experimental pancreatitis in mice Diabetes 58 2009 2148 2161
    • (2009) Diabetes , vol.58 , pp. 2148-2161
    • Koehler, J.A.1    Baggio, L.L.2    Lamont, B.J.3    Ali, S.4    Drucker, D.J.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.