Thiazolidin-4-one and thiazinan-4-one derivatives analogous to rosiglitazone as potential antihyperglycemic and antidyslipidemic agents

European Journal of Medicinal Chemistry

Volumn 63, Issue , 2013, Pages 611-620

  Raza, Saman ^a   Srivastava, Swayam P ^a   Srivastava, Daya S ^a   Srivastava, Arvind K ^a   Haq, W ^a   Katti, S B ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Antidyslipidemic; Antihyperglycemic; Insulin resistance reversal; Metformin; Rosiglitazone; Thiazolidin 4 ones

Indexed keywords

1 [4 [2 [METHYL(PYRIDIN 2 YL)AMINO]ETHOXY]PHENYL] 1,3 THIAZINAN 4 ONE; 2 [4 [2 [METHYL(PYRIDIN 2 YL)AMINO]ETHOXY]PHENYL]THIAZOLIDIN 4 ONE; 3 (4 CHLOROPHENYL) 2 [4 [2 [METHYL(PYRIDIN 2 YL)AMINO]ETHOXY]PHENYL]THIAZOLIDIN 4 ONE; 3 [2 (1H INDOL 3 YL)ETHYL] 2 [4 [2 [METHYL(PYRIDIN 2 YL)AMINO]ETHOXY]PHENYL]THIAZOLIDIN 4 ONE; 3 BENZYL 2 [4 [2 [METHYL(PYRIDIN 2 YL)AMINO]ETHOXY]PHENYL] 1,3 THIAZINAN 4 ONE; 3 BENZYL 2 [4 [2 [METHYL(PYRIDIN 2 YL)AMINO]ETHOXY]PHENYL]THIAZOLIDIN 4 ONE; 3 BENZYL 2 [4 [2 [METHYL(PYRIDIN 2 YL)AMINO]ETHOXY]PHENYL]THIAZOLIDIN 4 ONE SULFOXIDE; 3 BENZYL 5 METHYL 2 [4 [2 [METHYL(PYRIDIN 2 YL)AMINO]ETHOXY]PHENYL]THIAZOLIDIN 4 ONE; 3 BUTYL 2 [4 [2 [METHYL(PYRIDIN 2 YL)AMINO]ETHOXY]PHENYL] 1,3 THIAZINAN 4 ONE; 3 BUTYL 2 [4 [2 [METHYL(PYRIDIN 2 YL)AMINO]ETHOXY]PHENYL] THIAZOLIDIN 4 ONE SULFOXIDE; 3 BUTYL 2 [5 [2 [METHYL(PYRIDIN 2YL)AMINO]ETHOXY]PHENYL]THIAZOLIDIN 4 ONE; 3 BUTYL 5 METHYL 2 [4 [2 [METHYL(PYRIDIN 2 YL)AMINO]ETHOXY]PHENYL]THIAZOLIDIN 4 ONE; 3 CYCLOPROPYL 2 [4 [2 [METHYL(PYRIDIN 2 YL)AMINO]ETHOXY]PHENYL] 1,3 THIAZINAN 4 ONE; 3 CYCLOPROPYL 2 [4 [2 [METHYL(PYRIDIN 2 YL)AMINO]ETHOXY]PHENYL]THIAZOLIDIN 4 ONE; 3 ISOPROPYL 2 [4 [2 [METHYL(PRYIDIN 2 YL)AMINO]ETHOXY]PHENYL]THIAZOLIDIN 4 ONE; 3 ISOPROPYL 2 [4 [2 [METHYL(PYRIDIN 2 YL)AMINO]ETHOXY]PHENYL] 1,3 THIAZINAN 4 ONE; 3 OCTYL 2 [4 [2 [METHYL(PYRIDIN 2 YL)AMINO]ETHOXY]PHENYL] 1,3 THIAZINAN 4 ONE; 3 OCTYL 2 [4 [2 [METHYL(PYRIDIN 2 YL)AMINO]ETHOXY]PHENYL]THIAZOLIDIN 4 ONE; ANTIDIABETIC AGENT; ANTILIPEMIC AGENT; HIGH DENSITY LIPOPROTEIN CHOLESTEROL; LOW DENSITY LIPOPROTEIN CHOLESTEROL; METFORMIN; ROSIGLITAZONE; THIAZINE DERIVATIVE; THIAZOLIDINE DERIVATIVE; TRIACYLGLYCEROL; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIDIABETIC ACTIVITY; ARTICLE; CHOLESTEROL BLOOD LEVEL; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HYPERGLYCEMIA; IN VITRO STUDY; IN VIVO STUDY; MALE; MOUSE; NONHUMAN; ONE POT SYNTHESIS; ORAL GLUCOSE TOLERANCE TEST; POLYMERIZATION; TRIACYLGLYCEROL BLOOD LEVEL;

3T3-L1 CELLS; ANIMALS; BLOOD GLUCOSE; CELL DIFFERENTIATION; CELL LINE; DIABETES MELLITUS, TYPE 2; DOSE-RESPONSE RELATIONSHIP, DRUG; DYSLIPIDEMIAS; GLUCOSE; HYPOGLYCEMIC AGENTS; HYPOLIPIDEMIC AGENTS; MALE; MICE; MODELS, CHEMICAL; MOLECULAR STRUCTURE; MUSCLE, SKELETAL; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZINES; THIAZOLIDINEDIONES; THIAZOLIDINES; TRIGLYCERIDES;

EID: 84875936802     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.01.054     Document Type: Article

References (35)

1. S.E. Khan The relative contributions of insulin resistance and beta-cell dysfunction to the pathophysiology of type 2 diabetes Diabetologia 46 2003 3 19
2. J.S. Skyler Diabetes mellitus: pathogenesis and treatment strategies J. Med. Chem. 47 2004 4113 4117
3. B. Ahréna GLP-1 for type 2 diabetes Exp. Cell Res. 317 2011 1239 1245
4. G.J. Murphy, and J.C. Holder PPAR-γ agonists: therapeutic role in diabetes, inflammation and cancer Trends Pharmacol. Sci. 21 2000 469 474
5. Y. Momose Studies on antidiabetic agents. X. Synthesis and biological activities of pioglitazone and related compounds Chem. Pharm. Bull. 39 1991 1440 1445
6. B.C.C. Cantello The synthesis of BRL 49653-a novel and potent antihyperglycaemic agent Bioorg. Med. Chem. Lett. 4 1994 1181 1184
7. C. Knouff, and J. Auwerx Peroxisome proliferator-activated receptor-γ calls for activation in moderation: lessons from genetics and pharmacology Endocrinol. Rev. 25 2004 899 918
8. S. Singh, Y.K. Loke, and C.D. Furberg Long-term risk of cardiovascular events with rosiglitazone-a meta-analysis J. Am. Med. Assoc. 298 2007 1189 1195
9. A.K. McDonough The effect of thiazolidinediones on BMD and osteoporosis Nat. Clin. Pract. Endocrinol. Metab. 4 2008 507 513
10. S.E. Nissen, K. Wolski, and E.J. Topol Effect of muraglitazar on death and major adverse cardiovascular events in patients with type 2 diabetes mellitus J. Am. Med. Assoc. 294 2005 2581 2586
11. P.J. Larsen Dissociation of antihyperglycaemic and adverse effects of partial peroxisome proliferator-activated receptor (PPAR-γ) agonist balaglitazone Eur. J. Pharmacol. 596 2008 173 179
12. V.D. Pratik Design and synthesis of N-[(4-methoxyphenoxy)carbonyl]-N-[[4- [2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]methyl]glycine [muraglitazar/BMS-298585], a novel peroxisome proliferator-activated receptor α/γ dual agonist with efficacious glucose and lipid-lowering activities J. Med. Chem. 48 2005 2248 2250
13. J. Li Discovery of an oxybenzylglycine based peroxisome proliferator activated receptor α selective agonist 2-((3-((2-(4-chlorophenyl)-5- methyloxazol-4-yl)methoxy)benzyl)(methoxycarbonyl)amino)acetic acid (BMS-687453) J. Med. Chem. 53 2010 2854 2864
14. N. Masahiro (3-Substituted benzyl)thiazolidine-2,4-diones as structurally new antihyperglycemic agents Bioorg. Med. Chem. Lett. 9 1999 533 538
15. N. Mahindroo Novel indole-based peroxisome proliferator-activated receptor agonists: design, SAR, structural biology, and biological activities J. Med. Chem. 48 2005 8194 8208
16. N. Mahindroo Structural basis for the structure-activity relationships of peroxisome proliferator-activated receptor agonists J. Med. Chem. 49 2006 6421 6424
17. J.H. Ahn Indenone derivatives: a novel template for peroxisome proliferator-activated receptor γ (PPARγ) agonists J. Med. Chem. 49 2006 4781 4784
18. N. Mahindroo Indol-1-yl acetic acids as peroxisome proliferator-activated receptor agonists: design, synthesis, structural biology, and molecular docking studies J. Med. Chem. 49 2006 1212 1216
19. R. Epple Novel bisaryl substituted thiazoles and oxazoles as highly potent and selective peroxisome proliferator-activated receptor δ agonists J. Med. Chem. 53 2010 77 105
20. R.L. Dow Benzyloxazolidine-2,4-diones as potent hypoglycemic agents J. Med. Chem. 34 1991 1538 1544
21. H. Shinkai Isoxazolidine-3,5-dione and noncyclic 1,3-dicarbonyl compounds as hypoglycemic agents J. Med. Chem. 41 1998 1927 1933
22. K. Henriksen A comparison of glycemic control, water retention, and musculoskeletal effects of balaglitazone and pioglitazone in diet-induced obese rats Eur. J. Pharmacol. 616 2009 340 345
23. http://www.news-medical.net/news/20100104/Headline-results-from-first- phase-III-study-of-Balaglitazone-announced.aspx
24. S. Kanda Potent antidiabetic effects of rivoglitazone, a novel peroxisome proliferator-activated receptor-γ agonist, in obese diabetic rodent models J. Pharmacol. Sci. 111 2009 155 166
25. B.B. Lohray Novel euglycemic and hypolipidemic agents J. Med. Chem. 41 1998 1619 1630
26. T. Srivastava, W. Haq, and S.B. Katti Tetrahedron 58 2002 7619 7624
27. B.M. Trost, and D.P. Curran Chemoselective oxidation of sulfides to sulfones with potassium hydrogen persulfate Tetrahedron. Lett. 22 1981 1287 1290
28. A.K. Tamarkar Stimulatory effect of Ceriops tagal on hexose uptake in L6 muscle cells in culture Nat. Prod. Res. 22 2008 592 599
29. L. Herberg, and D.L. Coleman Laboratory animals exhibiting obesity and diabetes syndromes Metab. Clin. Exp. 26 1977 59 100
30. E.H. Leiter The genetics of diabetes susceptibility in mice FASEB J. 3 1989 2231 2241
31. M.J. Orland, and M.A. Permutt Quantitative analysis of pancreatic proinsulin mRNA in genetically diabetic (db/db) mice Diabetes 36 1987 341 347
32. O.A. MacDougald, and S. Mandrup Adipogenesis: forces that tip the scales Trends Endocrinol. Metab. 13 2002 5 11
33. X. Sheng, Y. Zhang, Z. Gong, C. Huang, and Y.Q. Zang Improved insulin resistance and lipid metabolism by cinnamon extract through activation of peroxisome proliferator-activated receptors PPAR Res. 2008 581348 10.1155/2008/581348 Published online 2008 December 11
34. S. Yonemitsu, H. Nishimura, and M. Shintani Troglitazone induces GLUT4 translocation in L6 myotubes Diabetes 50 2001 1093 1101
35. S. Pastromas, and S. Koulouris Thiazolidinediones: antidiabetic drugs with cardiovascular effects Hellenic J. Cardiol. 47 2006 352 360