Highly selective aldose reductase inhibitors. 1. 3-(Arylalkyl)-2,4,5-trioxoimidazolidine-1-acetic acids

Journal of Medicinal Chemistry

Volumn 39, Issue 9, 1996, Pages 1924-1927

  Ishii, Akira ^a   Kotani, Takayuki ^a   Nagaki, Yasuhiro ^a   Shibayama, Yoji ^a   Toyomaki, Yoshio ^a   Okukado, Nobuhisa ^a   Ienaga, Kazuharu ^a   Okamoto, Kaoru ^a  

^a Nippon Zoki Pharmaceutical Co   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,4,5 TRIOXOIMIDAZOLIDINE 1 ACETIC ACID DERIVATIVE; 3 (3 NITROBENZYL) 2,4,5 TRIOXOIMIDAZOLIDINE 1 ACETIC ACID; ALDEHYDE REDUCTASE; ALDOSE REDUCTASE INHIBITOR; ALRESTATIN; EPALRESTAT; NZ 314; PONALRESTAT; TOLRESTAT; UNCLASSIFIED DRUG; ZENARESTAT;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; KIDNEY; LENS; MALE; MOTOR NERVE CONDUCTION; NONHUMAN; RAT;

ACETIC ACIDS; ALDEHYDE REDUCTASE; ANIMALS; ENZYME INHIBITORS; GUINEA PIGS; KIDNEY; LENS, CRYSTALLINE; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; RATS;

EID: 0030007526     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9508393     Document Type: Article

References (21)

1. Kador, P. F. The Role of Aldose Reductase in the Development of Diabetic Complications. Med. Res. Rev. 1988, 8, 325-352.
2. Kador, P. F.; Kinoshita, J. H.; Sharpless, N. E. Aldose Reductase Inhibitors: A Potential New Class of Agents for the Pharmacological Control of Certain Diabetic Complications. J. Med. Chem. 1985, 28, 841-849.
3. Kador, P. F.; Robinson, W. G.; Kinoshita, J. H. The Pharmacology of Aldose Reductase Inhibitors. Annu. Rev. Pharmacol. Toxicol. 1985. 25, 691-714.
4. Tanimoto, T.; Nishimura, C. Biochemistry and Clinical Significance of Aldose Reductase. Peripheral Nerve 1993, 4, 149-158.
5. Srivastava, S. K.; Petrash, J. M.; Sadana, I. J.; Ansari, N. H.; Partridge, C. A. Susceptibility of Aldehyde and Aldose Reductases of Human Tissues to Aldose Reductase Inhibitors. Curr. Eye Res. 1982, 2, 407-410.
6. Poulsom, R. Inhibition of Hexonate Dehydrogenase and Aldose Reductase from Bovine Retina by Sorbinil, Statil, M79175 and Valproate. Biochem. Pharmacol. 1986, 35, 2955-2959.
7. Tanimoto, T.; Nishiyama, C. Molecularbiology of Aldose Reductase. Exp. Med. 1991, 9, 541-547.
8. Tanimoto, T.; Nishimura, C. Molecular Structure and Function of Aldose Reductase. J. Clin. Exp. Med. (Igaku No Ayumi) 1991, 156, 998-1002.
9. Hotta, N.; Sakamoto, N. Polyol Pathway and Diabetic Complications. Metab. Dis. 1989, 26, 621-632.
10. Kador, P. F.; Kinoshita, J. H.; Brittain, D. R.; Mirrlees, D. J.; Sennitt, C. M.; Stribling, D. Purified Rat Lens Aldose Reductase. Polyol Production in vitro and its Inhibition by Aldose Reductase Inhibitors. Biochem. J. 1986, 240, 233-237.
11. Takahashi, N.; Saito, T., Tomita, K. Purification and Properties of an NADPH-linked Aldehyde Reductase from Rat Kidney. Biochim. Biophys. Acta 1983, 748, 444-452.
12. Lee, Y. S.; Pearlstein, R.; Kador, P. F. Molecular Modeling Studies of Aldose Reductase Inhibitors. J. Med. Chem. 1994, 37, 787-792.
13. Morjana, N.; Flynn, T. G. Aldose Reductase from Human Psoas Muscle; Purification, Substrate Specificity, Immunological Characterization, and Effect of Drugs and Inhibitors. J. Biol. Chem. 1989, 264, 2906-2911.
14. Morjana, N.; Lyons, C.; Flynn, T. G. Aldose Reductase from Human Psoas Muscle: Affinity Labeling of an Active Site Lysine by Pyridoxal 5′-Phosphate and Pyridoxal 5′-Diphospho-5′-Adenosine. J. Biol. Chem. 1989, 264, 2912-2919.
15. Bohren, K. M.; Bullock, B.; Wermuth, B.; Gabbay, K. H. The Aldo-Keto Reductase Superfamily: cDNA and deduced Amino Acid Sequences of Human Aldehyde and Aldose Reductases. J. Biol. Chem. 1989, 264, 9547-9551.
16. Sato, S.; Kador, P. F. Inhibition of Aldehyde Reductase by Aldose Reductase Inhibitors. Biochem. Pharmacol. 1990, 40, 1033-1042
17. Smar, M. W.; Ares, J. J.; Nakayama, T.; Itabe, H.; Kador, P. F.; Miller, D. D. Selective Irreversible Inhibitors of Aldose Reductase. J. Med. Chem. 1992, 35, 1117-1120.
18. Dvornik, D. In Aldose Reductase Inhibition: An Approach to the Prevention of Diabetic Complications. Biomedical Information Corporation; Porte, D., Ed.; McGraw-Hill: New York, 1987; Chapter 4.
19. Cromlish, J. A.; Flynn, T. G. Identification of Pig Brain Aldehyde Reductases with High-Km Aldehyde Reductase, the Low-Km Aldehyde Reductase and Aldose Reductase, Carbonyl Reductase, and Succinic Semialdehyde Reductase. J. Neurochem. 1985, 44, 1485-1493.
20. Nagaki, Y.; et al. Studies on New Aldose Reductase Inhibitor NZ-314 I-III. J. Jpn. Diabetes Soc. 1995, 38 (Suppl. 1), 377.
21. Mylari, B. L.; Beyer, T. A.; Siegel, T. W. A Highly Specific Aldose Reductase Inhibitor, Ethyl 1-Benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate, and Its Congeners. J. Med. Chem. 1991, 34, 1011-1018.