1,668
Views
4
CrossRef citations to date
0
Altmetric
Article

Effect of 6-Benzoyl-benzothiazol-2-one scaffold on the pharmacological profile of α-alkoxyphenylpropionic acid derived PPAR agonists

, , , , , , , , , & show all
Pages 524-538 | Received 21 Oct 2019, Accepted 05 Jan 2020, Published online: 15 Jan 2020

References

  • Pirat C, Farce A, Lebegue N, et al. Targeting peroxisome proliferator-activated receptors (PPARs): development of modulators. J Med Chem 2012;55:4027–61.
  • Rogler G. Significance of anti-inflammatory effects of PPAR agonists? Gut 2005;55:1067–9.
  • Tan CK, Zhuang Y, Wahli W. Synthetic and natural Peroxisome Proliferator-Activated Receptor (PPAR) agonists as candidates for the therapy of the metabolic syndrome. Expert Opin Ther Targets 2017;21:333–48.
  • Ivanova EA, Parolari A, Myasoedova V, et al. Peroxisome proliferator-activated receptor (PPAR) gamma in cardiovascular disorders and cardiovascular surgery. J Cardiol 2015;66:271–8.
  • Chung JH, Seo AY, Chung SW, et al. Molecular mechanism of PPAR in the regulation of age-related inflammation. Ageing Res Rev 2008;7:126–36.
  • Botta M, Audano M, Sahebkar A, et al. PPAR agonists and metabolic syndrome: an established role? Int J Mol Sci 2018;19:1197.
  • Hong F, Xu P, Zhai Y. The opportunities and challenges of peroxisome proliferator-activated receptors ligands in clinical drug discovery and development. Int J Mol Sci 2018;19:2189.
  • Yki-Järvinen H. Thiazolidinediones. N Engl J Med 2004;351:1106–18.
  • Lago RM, Singh PP, Nesto RW. Congestive heart failure and cardiovascular death in patients with prediabetes and type 2 diabetes given thiazolidinediones: a meta-analysis of randomised clinical trials. Lancet 2007;370:1129–36.
  • Bailey CJ. Learning from tesaglitazar. Diab Vasc Dis Res 2007;4:161–2.
  • Zhang J, Liu X, Xie XB, et al. Multitargeted bioactive ligands for PPARs discovered in the last decade. Chem Biol Drug Des 2016;88:635–63.
  • Motani A, Wang Z, Weiszmann J, et al. INT131: a selective modulator of PPARγ. J Mol Biol 2009;386:1301–11.
  • Lee DH, Huang H, Choi K, et al. Selective PPARγ modulator INT131 normalizes insulin signaling defects and improves bone mass in diet-induced obese mice. Am J Physiol Endocrinol Metab 2012;302:E552–60.
  • Zhang F, Lavan BE, Gregoire FM. Selective modulators of PPAR-gamma activity: molecular aspects related to obesity and side-effects. PPAR Res 2007;2007:32696.
  • Le Naour M, Leclerc V, Farce A, et al. Effect of oxime ether incorporation in acyl indole derivatives on PPAR subtype selectivity. ChemMedChem 2012;7:2179–93.
  • Regitz M, Anschutz W, Liedhegener A. Reaktionen CH-aktiver Verbindungen mit Aziden, XXIII Synthese von α-Diazo-phosphonsäureestern. Chem Ber 1968;101:3734–43.
  • Haigh D, Birrell HC, Cantello BCC, et al. Non-thiazolidinedione antihyperglycaemic agents. Part 4: synthesis of (±)-, (R)-(+)- and (S)-(−)-enantiomers of 2-oxy-3-arylpropanoic acids. Tetrahedron: Asymmetry 1999;10:1335–51.
  • Ferry G, Bruneau V, Beauverger P, et al. Binding of prostaglandins to human PPARγ: tool assessment and new natural ligands. Eur J Pharmacol 2001;417:77–89.
  • Staels B, Koenig W, Habib A, et al. Activation of human aortic smooth-muscle cells is inhibited by PPARα but not by PPARγ activators. Nature 1998;393:790–3.
  • Kliewer SA, Umesono K, Noonan DJ, et al. Convergence of 9-cis retinoic acid and peroxisome proliferator signalling pathways through heterodimer formation of their receptors. Nature 1992;358:771–4.
  • Clark M, Cramer IIR, van Opdenbosch N. Validation of the general purpose tripos 5.2 force field. J Comput Chem 1989;10:982–1012.
  • Pettersen EF, Goddard TD, Huang CC, Couch GS, et al. UCSF Chimera? A visualization system for exploratory research and analysis. J Comput Chem 2004;25:1605–12.
  • Trott O, Olson AJ. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 2010;31:455–61.
  • Pirat C, Ultré V, Lebegue N, et al. New Access to 5-Substituted 1,3-Benzothiazol-2(3H)-ones and Their N-Methyl Analogues by a Palladium Coupling Reaction. Synthesis 2011;24:480–4.
  • Yous S, Poupaert JH, Lesieur I, et al. AlCl3-DMF reagent in the Friedel-crafts reaction. Application to the acylation reaction of 2(3H)-benzothiazolones. J Org Chem 1994;59:1574–6.
  • Carato P, Moussavi Z, Sabaouni A, et al. Synthesis of 6- and 7-acyl-4H-benzothiazin-3-ones. Tetrahedron 2006;62:9054–8.
  • Hurtevent A, L’Helgoual’ch JM, Carato P, Lebegue N, Leclerc V, Berthelot P, Dacquet C, Ktorza A, Caignard DH. Int Patent PCT FR 06/000175; 2006.
  • Moussavi Z, Lesieur D, Lespagnol C, et al. 7-Acyl-2,3-dihydro-1,4-benzoxazin-3-ones and normolipemic properties. Eur J Med Chem 1989;24:54–60.
  • Poupaert JH, Depreux P, McCurdy CR. Unsymmetrical diarylketones from electron-rich Heterocyclic arenes. Monatsh Chem 2003;134:823–30.
  • Torres JC, Garden SJ, Pinto AC, et al. A synthesis of 3-fluoroindoles and 3,3-difluoroindolines by reduction of 3,3-difluoro-2-oxindoles using a borane tetrahydrofuran complex. Tetrahedron 1999;55:1881–92.
  • Xu J, Jain N, Sui Z. Halogen–magnesium exchange of m- and p-iodo or bromo-arenes bearing ortho-directing groups through ate complexes. Tetrahedron Lett 2004;45:6399–402.
  • Dess DB, Martin JC. A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species. J Am Chem Soc 1991;113:7277–87.
  • Pirat C, Dacquet C, Leclerc V, et al. Anti-diabetic activity of fused PPARγ-SIRT1 ligands with limited body-weight gain by mimicking calorie restriction and decreasing SGK1 expression. Eur J Med Chem 2017;137:310–26.
  • Gillis EP, Eastman KJ, Hill MD, et al. Applications of fluorine in medicinal chemistry. J Med Chem 2015;58:8315–59.
  • Kuhn B, Hilpert H, Benz J, et al. Structure-based design of indole propionic acids as novel PPARα/γ co-agonists. Bioorg Med Chem Lett 2006;16:4016–20.,
  • Parmenon C, Guillard J, Caignard DH, et al. 4,4-Dimethyl-1,2,3,4-tetrahydroquinoline-based PPARα/γ agonists. Part. II: synthesis and pharmacological evaluation of oxime and acidic head group structural variations. Bioorg Med Chem Lett 2009;19:2683–7.
  • Cronet P, Petersen JF, Folmer R, et al. Structure of the PPARα and -γ ligand binding domain in complex with AZ 242; ligand selectivity and agonist activation in the PPAR family. Structure 2001;9:699–701.
  • van Breemen RB, Li Y. Caco-2 cell permeability assays to measure drug absorption. Exp Opin Drug Metab Toxicol 2005;1:175–85.