Isoxazolidine-3,5-dione and noncyclic 1,3-dicarbonyl compounds as hypoglycemic agents

Journal of Medicinal Chemistry

Volumn 41, Issue 11, 1998, Pages 1927-1933

  Shinkai, Hisashi ^a   Onogi, Syoji ^a   Tanaka, Masahiro ^a   Shibata, Tsutomu ^a   Iwao, Megumi ^a   Wakitani, Korekiyo ^a   Uchida, Itsuo ^a  

^a JT Inc   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,4 THIAZOLIDINEDIONE DERIVATIVE; ANTIDIABETIC AGENT; CARBONYL DERIVATIVE; ISOXAZOLIDINE 3,5 DIONE; ISOXAZOLIDINE DERIVATIVE; MALONIC ACID DERIVATIVE; TROGLITAZONE; UNCLASSIFIED DRUG;

ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG ACTIVITY; DRUG STRUCTURE; GLUCOSE BLOOD LEVEL; HYPOGLYCEMIA; MALE; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

3T3 CELLS; ANIMALS; BLOOD GLUCOSE; CELL DIFFERENTIATION; DRUG EVALUATION, PRECLINICAL; HYPOGLYCEMIC AGENTS; INSULIN; ISOXAZOLES; L CELLS (CELL LINE); MALE; MALONATES; MICE; OXAZOLES; TRIGLYCERIDES;

EID: 0032554866     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970771m     Document Type: Article

References (21)

1. Porte, D., Jr.; Schwartz, M. W. Diabetes Complications: Why Is Glucose Potentially Toxic? Science 1996, 272, 699-700.
2. The Diabetes Control and Complications Trial Research Group. The Effect of Intensive Treatment on the Development and Progression of Long-Term Complications in Insulin-Dependent Diabetes Mellitus. N. Engl. J. Med. 1993, 329, 977-986.
3. Taylor, S. I.; Accili, D.; Imai, Y. Insulin Resistance or Insulin Deficiency. Which Is the Primary Cause of NIDDM? Diabetes 1994, 43, 735-740.
4. (a) Sohda, T.; Mizuno, K.; Imamiya, E.; Sugiyama, Y.; Fujita, T.; Kawamatsu, Y. Studies on Antidiabetic Agents. II. Synthesis of 5-[4-(1-Methylyclohexylmethoxy)benzyl]thiazolidine-2,4-dione (ADD-3878) and Its Derivatives. Chem. Pharm. Bull. 1982, 30, 3580-3600.
5. (b) Fujita, T.; Sugiyama, Y.; Taketomi, S.; Sohda, T.; Kawamatsu, Y.; Iwatsuka, H.; Suzuoki, Z. Reduction of Insulin Resistance in Obese and Diabetic Animals by 5-[4-(1-Methylcyclohexylmethoxy)benzyl]thiazolidine-2,4-dione (ADD-3878, U-63,287, Ciglitazone), a New Antidiabetic Agent. Diabetes 1983, 32, 804-810.
6. Hulin, B.; McCarthy, P. A.; Gibbs, E. M. The Glitazone Family of Antidiabetic Agents. Curr. Pharm. Des. 1996, 2, 85-102.
7. Sohda, T.; Mizuno, K.; Momose, Y.; Ikeda, H.; Fujita, T.; Meguro, K. Studies on Antidiabetic Agents. 11. Novel Thiazolidinedione Derivatives as Potent Hypoglycemic and Hypolipidemic Agents. J. Med. Chem. 1992, 35, 2617-2626.
8. Sohda, T.; Mizuno, K.; Tawada, H..; Sugiyama, Y.; Fujita, T.; Kawamatsu, Y. Studies on Antidiabetic Agents. I. Synthesis of 5-[4-(2-Methyl-2-phenylpropoxy)benzyl]thiazolidine-2,4-dione(AL-321) and Related Compounds. Chem. Pharm. Bull. 1982, 30, 3563-3573.
9. Dow, R. L.; Bechle, B. M.; Chou, T. T.; Clark, D. A.; Hulin, B.; Stevenson, R. W. Benzyloxyazolidine-2,4-diones as Potent Hypoglycemic Agents. J. Med. Chem. 1991, 34, 1538-1544.
10. Goldstein, S. W.; McDermott, R. E.; Gibbs, E. M.; Stevenson, R. W. Hydroxyurea Derivatives as Hypoglycemic Agents. J. Med. Chem. 1993, 36, 2238-2240.
11. Hulin, B.; Newton, L. S.; Lewis, D. M.; Generux, P. E.; Gibbs, E. M.; Clark, D. A. Hypoglycemic Activity of a Series of α-Alkylthio and α-Alkoxy Carboxylic Acids Related to Ciglitazone. J. Med. Chem. 1996, 39, 3897-3907.
12. (a) Buckle, D. R.; Cantello, B. C. C.; Cawthorne, M. A.; Coyle, P. J.; Dean, D. K.; Faller, A.; Haigh, D.; Hindley, R. M.; Jefcott, L. J.; Lister, C. A.; Pinto, I. L.; Rami, H. K.; Smith, D. G.; Smith, S. A. Non Thiazolidinedione Antihyperglycemic Agents. 1: α-Heteroatom Substituted β-Phenylpropanoic Acids. Bioorg. Med. Chem. Lett. 1996, 6, 2121-2126.
13. (b) Buckle, D. R.; Cantello, B. C. C.; Cawthorne, M. A.; Coyle, P. J.; Dean, D. K.; Faller, A.; Haigh, D.; Hindley, R. M.; Jefcott, L. J.; Lister, C. A.; Pinto, I. L.; Rami, H. K.; Smith, D. G.; Smith, S. A Non Thiazolidinedione Antihyperglycemic Agents. 2: α-Carbon Substituted β-Phenyl-propanoic Acids. Bioorg. Med. Chem. Lett. 1996, 6, 2127-2130.
14. 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 γ(PPARγ). J. Biol. Chem. 1995, 270, 12953-12956.
15. Willson, T. M.; Cobb, J. E.; Cowan, D. J.; Wiethe, R. W.; Correa, I. D.; Prakash, S. R.; Beck, K. D.; Moore, L. B.; Kliewer, S. A.; Lehmann, J. M. The Structure-Activity Relationship between Peroxisome Proliferator-Activated Receptor γ Agonism and the Antihyperglycemic Activity of Thiazolidinediones. J. Med. Chem. 1996, 39, 665-668.
16. Hulin, B.; Clark, D. A.; Goldstein, S. W.; McDermott, R. E.; Dambek, P. J.; Kappeler, W. H.; Lamphere, C. H.; Lewis, D. M.; Rizzi, J. P. Novel Thiazolidine-2,4-diones as Potent Euglycemic Agents. J. Med. Chem. 1992, 35, 1853-1864.
17. Momose, Y.;Meguro, K.; Ikeda, H.; Hatanaka, C.; Oi, S. Sohda, T. Studies on Antidiabetic Agents. X. Synthesis and Biological Activities of Pioglitazone and Related Compounds. Chem. Pharm. Bull. 1991, 39, 1440-1445.
18. Zask, A.; Jirkovsky, I.; Nowicki, J. W.; McCaleb, M. L. Synthesis and Antihyperglycemic Activity of Novel 5-(Naphthalenylsulfonyl)-2,4-thiazolidinediones. J. Med. Chem. 1990, 33, 1418-1423.
19. Zvilichovsky, G. Disic Acids. A Study of a New Series of Strong Organic Acids and their Condensation Products with Aldehydes. Tetrahedron 1975, 31, 1861-1867.
20. Iwatsuka, H.; Shino, A.; Suzuoki, Z. General Survey of Diabetic Features of Yellow KK Mice. Endocrinol. Jpn. 1970, 17, 23-35.
21. Kletzien, R. F.; Clarke, S. D.; Ulrich, R. G. Enhancement of Adipocyte Differentiation by an Insulin-Sensitizing Agent. Mol. Pharmacol. 1991, 41, 393-398.