Novel, highly potent aldose reductase inhibitors: Cyano(2-oxo-2,3-dihydroindol-3-yl)acetic acid derivatives

Journal of Medicinal Chemistry

Volumn 46, Issue 8, 2003, Pages 1419-1428

  Da Settimo, Federico ^a   Primofiore, Giampaolo ^a   Da Settimo, Antonio ^a   La Motta, Concettina ^a   Simorini, Francesca ^a   Novellino, Ettore ^b   Greco, Giovanni ^b   Lavecchia, Antonio ^b   Boldrini, Enrico ^c  

^a UNIVERSITY OF PISA   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^c Farmigea SpA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOSE REDUCTASE INHIBITOR; ALRESTATIN; CYANO(2 OXO 2,3 DIHYDROINDOL 3 YL)ACETIC ACID; CYANO[5 FLUORO 1 (4 METHYLBENZYL) 2 OXO 2,3 DIHYDROINDOL 3 YL]ACETIC ACID; CYANO[5 FLUORO 1 (4 METHYLBENZYL) 2 OXO 2,3 DIHYDROINDOL 3 YL]ACETIC ACID ISOPROPYL ESTER; EPALRESTAT; GLUTATHIONE REDUCTASE; IDITOL DEHYDROGENASE; QUERCETIN; SORBINIL; TOLRESTAT; UNCLASSIFIED DRUG; ZOPOLRESTAT;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CATALYSIS; CATARACT; CONCENTRATION RESPONSE; DRUG ACTIVITY; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; TREATMENT OUTCOME;

ACETIC ACIDS; ALDEHYDE REDUCTASE; ANIMALS; CATARACT; ENZYME INHIBITORS; GALACTOSEMIAS; HUMANS; INDOLES; MODELS, MOLECULAR; OPHTHALMIC SOLUTIONS; RATS; RATS, SPRAGUE-DAWLEY; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037431379     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030762f     Document Type: Article

References (56)

1. Kador, P. F. The Role of Aldose Reductase in the Development of Diabetic Complications. Med. Res. Rev. 1988, 8, 325-352.
2. Tomlison, D. R.; Stevens, E. J.; Diemel, L. T. Aldose Reductase Inhibitors and Their Potential for the Treatment of Diabetic Complications. Trends Pharmacol. Sci. 1994, 293-297.
3. Ammon, H. P. T.; Häring, H. U.; Kellerer, M.; Laube, H.; Mosthaf, L.; Verspohl, E. J.; Wahl, M. A. Antidiabetic Agents. Recent Advances in Their Molecular and Clinical Pharmacology. Adv. Drug Res. 1996, 27, 171-178.
4. Ashizawa, N.; Tomoji, A. Benzothiazole Aldose Reductase Inhibitors. Drugs Future 1998, 23, 521-529.
5. Costantino, L.; Rastelli, G.; Vianello, P.; Cignarella, G.; Barlocco, D. Diabetes Complications and Their Potential Prevention: Aldose Reductase Inhibition and Other Approaches. Med. Res. Rev. 1999, 19, 3-23.
6. Sarges, R.; Oates, P. J. Aldose Reductase Inhibitors: Recent Developments. Prog. Drug Res. 1993, 40, 99-161.
7. Da Settimo, F.; Primofiore, G.; Da Settimo, A.; La Motta, C.; Taliani, S.; Simorini, F.; Novellino, E.; Greco, G.; Lavecchia, A.; Boldrini, E. [1,2,4]Triazino[4,3-a]benzimidazole Acetic Acid Derivatives: A New Class of Selective Aldose Reductase Inhibitors. J. Med. Chem. 2001, 44, 4359-4369.
8. Da Settimo, A.; Menicagli, C.; Nannipieri, E. Reactions of 2,3-Dibromoindole Derivatives with Bromine and Other Oxidizing Agents. 2,3-Dibromoindole → 3,3-Dibromooxindole Transformation. J. Org. Chem. 1974, 39, 1995-1998.
9. Da Settimo, A.; Santerini, V.; Primofiore, G.; Biagi, G.; Veneziano, C. Bromination of Indole, Skatole and 2-Methylindole. Oxidation of 2-Bromoindole Derivatives. Gazz. Chim. Ital. 1977, 107, 367-372.
10. Da Settimo, A.; Primofiore, G.; Ferrarini, P. L.; Franzone J. S.; Rocco, C.; Cravanzola, C. Bromoderivatives of Gramines. Preparation and Pharmacological Properties. Eur. J. Med. Chem. 1983, 18, 261-267.
11. Primofiore, G.; Da Settimo, F.; Taliani, S.; Marini, A. M.; Novellino, E.; Greco, G.; Lavecchia, A.; Besnard, F.; Trincavelli, L.; Costa, B.; Martini, C. Novel N-(Arylalkyl)indol-3-ylglyoxylylamides Targeted as Ligands of the Benzodiazepine Receptor: Synthesis Biological Evaluation, and Molecular Modeling Analysis of the structure - Activity Relationships. J. Med. Chem. 2001, 44, 2286-2297.
12. Howard, H. R.; Sarges, R.; Siegel, T. W.; Beyer, T. A. Synthesis and Aldose Reductase Inhibitory Activity of Substituted 2(1H)-Benzimidazolone- and Oxindole-1-acetic Acids. Eur. J. Med. Chem. 1992, 27, 779-789.
13. Brittain, D. R.; Wood, R. Indoline Derivatives. Eur. Pat. Appl. EP 125,090; Chem. Abstr. 1985, 102, 113493f.
14. Brittain, D. R.; Wood, R. Indoline Derivatives. Eur. Pat. Appl. EP 125,090; Chem. Abstr. 1985, 102, 113493f.
15. Szabo-Pusztay, K.; Szabo, L. A Simple General Method for the Oxidation of Indoles to Oxindoles. Synthesis 1979, 276-277.
16. Wilson, D. K.; Tarle, I.; Petrash, J. M.; Quiocho, F. A. Refined 1.8 A Structure of Human Aldose Reductase Complexed with the Potent Inhibitor Zopolrestat. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 9847-9851.
17. Pietra, S. Indole Derivatives. Farmaco 1957, 12, 946-953.
18. Harley-Mason, J.; Ingleby, R. F. J. Hydroxytryptamines. Part IV. Synthesis and Reactions of 2-3′-Oxindolylethylamines. J. Chem. Soc. 1958, 3639-3642.
19. Allen, F. H.; Bellard, S.; Brice, M. D.; Cartwright, B. A.; Doubleday: A.; Higgs, H.; Hummelink, T.; Hummelink-Peters, B. G.; Kennard, O.; Motherwell, W. D. S.; Rodgers, J. R.; Watson, D. G. The Cambridge Crystallographic Data Centre: Computer-Based Search, Retrieval, Analysis and Display of Information. Acta Crystallogr. 1979, B35, 2331-2339.
20. Morales-Rios, M. S.; Bucio-Vasquez, Ma. A.; Joseph-Nathan, P. Novel Oxidations of 1,3-Disubstituted Indoles. J. Heterocycl. Chem. 1993, 30, 953-956.
21. Daisley, R. W.; Walker, J. Substituted Oxindoles. Pt VII. Oxindole Analogues of Tryptamine and its Derivatives. Eur. J. Med. Chem. 1979, 14, 47-52.
22. Tacconi, G.; Righetti, P. P.; Desimoni, G. Preparation of N-Substituted Isatins. J. Prakt. Chem. 1973, 315, 339-344.
23. De Ruiter, J.; Brubaker, A. N.; Garner, M. A.; Barksdale, J. M.; Mayfield, C. A. In Vitro Aldose Reductase Inhibitory Activity of Substituted N-benzenesulfonylglycine Derivatives J. Pharm. Sci. 1987, 76, 149-152.
24. Mayfield, C. A.; De Ruiter, J. Novel Inhibitors of Rat Lens Aldose Reductase: N-[[(substituted amino)phenyl]sulfonyl]glycines. J. Med. Chem. 1987, 30, 1595-1598.
25. 50 with Bovine and Rat Lens Extracts. Ophthalmic Res. 1985, 17, 115-119.
26. Hockwin, O.; Müller, P.; Krolczyk, J.; McCue, B. A.; Mayer, P. R. Determination of AL01576 Concentration In Rat Lenses and Plasma by Bioassay for Aldose Reductase Activity Measurements. Ophthalmic Res. 1989, 21, 285-291.
27. Hu, T.; Merola, L. O.; Kuwabara, T.; Kinoshita, J. H. Prevention and Reversal of Galactose Cataract in Rats with Topical Sorbinil. Invest. Ophthalmol. Vis. Sci. 1984, 25, 603-605.
28. Sestanj, K.; Bellini, F.; Fung, S.; Abraham, N.; Treasurywala, A.; Humber, L.; Simard-Duquesne, N.; Dvornik, D. N-[5-(Trifluoromethyl)-6-methoxy-1-naphthalenyl]thioxomethyl]-N-methylglycine (Tolrestat), a Potent, Orally Active Aldose Reductase Inhibitor. J. Med. Chem. 1984, 27, 255-256.
29. Banditelli, S.; Boldrini, E.; Vilardo, G. P.; Cecconi, I.; Cappiello, M.; Dal Monte, M.; Marini, I.; Del Corso, A.; Mura, U. A New Approach Against Sugar Cataract Through Aldose Reductase Inhibitors. Exp. Eye Res. 1999, 69, 533-538.
30. Chaudhry, P. S.; Cabrera, J.; Juliani, H. R.; Varma, S. D. Inhibition of Human Lens Aldose Reductase by Flavonoids, Sulindac and Indomethacin. Biochem. Pharmacol. 1983, 32, 1995-1998.
31. Lindstad, R. I.; Hermansen, L. F.; McKinley-McKee, J. S. Inhibition and activation studies on sheep liver sorbitol dehydrogenase. Eur. J. Biochem. 1994, 221, 847-854.
32. Ward, W. H. J.; Sennitt, C. M.; Ross, H.; Dingle, A.; Timmus, D.; Mirrless, D. J.; Tuffin, D. P. Ponalrestat, a Potent and Specific Inhibitor of Aldose Reductase. Biochem. Pharmacol. 1990, 39, 337-346.
33. Fitzgerald, G. B.; Bauman, C.; Sajjat Hussoin, Md.; Wick, M. M. 2,4-dihydroxy benzylamine: a specific inhibitor of glutathione reductase. Biochem. Pharmacol. 1991, 41, 185-190.
34. 2α, and Its Isopropyl Ester in Vitro. Int. J. Pharm. 1987, 37, 27-32.
35. Suhonen, P.; Järvinen, T.; Peura, P.; Urtti, A. Permeability of Pilocarpic Acid Diesters Across Albino Rabbit Cornea in Vitro. Int. J. Pharm. 1991, 74, 221-228.
36. 2α. Prodrugs in Rabbit Cornea and Conjunctiva. J. Pharm. Sci. 1997, 86, 1180-1186.
37. Meng, E. C.; Shoichet, B. K.; Kuntz, I. D. Automated Docking with Grid-Based Energy Evaluation. J. Comput. Chem. 1992, 13, 505-524.
38. Meng, E. C.; Gschwend, D. A.; Blaney, J. M.; Kuntz, I. D. Orientational Sampling and Rigid-Body Minimization in Molecular Docking. Proteins: Struct., Funct., Genet. 1993, 17, 266-278.
39. Shoichet, B. K.; Bodian, D. L.; Kuntz, I. D. Molecular Modeling Using Shape Descriptors. J. Comput. Chem. 1992, 13, 380-397.
40. Connolly, M.; Gschwend, D. A.; Good, A. C.; Oshiro, C.; Kuntz, I. D. DOCK 3.5; Department of Pharmaceutical Chemistry, University of California: San Francisco, CA, 1995.
41. Pietra, S.; Indole Derivatives. Farmaco 1958, 13, 75-79.
42. Arbuzov, A. E.; Bastanova, M. Sh. Tautomerism of Isatin. Izvest. Akad. Nuak S. S. S. R., Otdel. Khim. Nauk 1952, 459-470; Chem. Abstr. 1953, 47, 4876b.
43. Arbuzov, A. E.; Bastanova, M. Sh. Tautomerism of Isatin. Izvest. Akad. Nuak S. S. S. R., Otdel. Khim. Nauk 1952, 459-470; Chem. Abstr. 1953, 47, 4876b.
44. Tacconi, G.; Gamba, A.; Marinone, F.; Desimoni, G. Heterodiene Syntheses-V. 1,2-Versus 1,4-Cycloaddition Reactions of Enamines to N-Substituted 3-Oxindolideneacetophenones. Tetrahedron 1971, 27, 561-579.
45. Sadler, P. W. Synthesis of Antiviral Agents. Part I. Heterocyclic Compounds Related to Isatin 3-Thiosemicarbazone. J. Chem. Soc. 1961, 243-246.
46. Hayman, S.; Kinoshita, J. H. Isolation and Properties of Lens Aldose Reductase. J. Biol. Chem. 1965, 240, 877-882.
47. Sybyl Molecular Modelling System (version 6.8); Tripos: St. Louis, MO.
48. Vinter, J. G.; Davis, A.; Saunders, M. R. Strategic Approaches to Drug Design. 1. An Integrated Software Framework for Molecular Modelling. J. Comput.-Aided Mol. Des. 1987, 1, 31-55.
49. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. AM1: a New General Purpose Mechanical Molecular Model. J. Am. Chem. Soc. 1985, 107, 3902-3909.
50. MOPAC (version 6.0) is available from Quantum Chemistry Program Exchange, No. 455.
51. Pearlman, D. A.; Case, D. A.; Caldwell, J. W.; Ross, W. S.; Cheatham, T. E., III.; Debolt, S.; Ferguson, D. M.; Seibel, G. L.; Kollman, P. A. AMBER, a Package of Computer Programs for Applying Molecular Mechanics, Normal-Mode Analysis, Molecular Dynamics and Free Energy Calculations to Simulate the Structural and Energetic Properties of Molecules. Comput. Phys. Commun. 1995, 91, 1-41.
52. Pearlman, D. A.; Case, D. A.; Caldwell, J. W.; Ross, W. S.; Cheatham, T. E., III; Ferguson, D. M.; Seibel, G.; Singh, U. C.; Weiner, P. K.; Kollman, P. A. AMBER 4.1; Department of Pharmaceutical Chemistry, University of California: San Francisco, CA, 1995.
53. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. A Second Generation Force Field for the Simulation of Proteins, Nucleic Acids, and Organic Molecules. J. Am. Chem. Soc. 1995, 117, 5179-5197.
54. Head, J.; Zerner, M. C. A Broyden-Fletcher-Goldfarb-Shanno Optimization Procedure for Molecular Geometries. Chem. Phys. Lett. 1985, 122, 264-274.
55. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J. D.; Impey, R.; W.; Klein, M. L. Comparison of Simple Potential Functions for Simulating Liquid Water. J. Chem. Phys. 1983, 79, 926-935.
56. Berendsen, H. J. C.; Postma, J. P. M.; van Gunsteren, W. F.; DiNola, A.; Haak, J. R. Molecular Dynamics with Coupling to an External Bath. J. Chem. Phys. 1984, 81, 3684-3690.