[1,2,4]Triazino[4,3-a]benzimidazole acetic acid derivatives: A new class of selective aldose reductase inhibitors

Journal of Medicinal Chemistry

Volumn 44, Issue 25, 2001, Pages 4359-4369

  Da Settimo, F ^a   Boldrini, E ^a,c   Primofiore, G ^a   Da Settimo, A ^a   La Motta, C ^a   Taliani, S ^a   Simorini, F ^a   Novellino, E ^a,b   Greco, G ^a,b   Lavecchia, A ^a,b  

^a UNIVERSITY OF PISA   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^c Farmigea SpA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

[1,2,4]TRIAZINO[4,3 A]BENZIMIDAZOLE ACETIC ACID DERIVATIVE; ACETIC ACID DERIVATIVE; ALDOSE REDUCTASE INHIBITOR; ALRESTATIN; EPALRESTAT; QUERCETIN; SORBINIL; TOLRESTAT; UNCLASSIFIED DRUG; ZOPOLRESTAT;

ANIMAL EXPERIMENT; ARTICLE; CATARACT; CONTROLLED STUDY; DRUG EFFECT; DRUG PROTEIN BINDING; DRUG SYNTHESIS; ENZYME ACTIVE SITE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ACETIC ACIDS; ALDEHYDE REDUCTASE; ANIMALS; BENZIMIDAZOLES; BINDING SITES; CATARACT; ENZYME INHIBITORS; GALACTOSEMIAS; HUMANS; MODELS, MOLECULAR; OPHTHALMIC SOLUTIONS; PROTEIN BINDING; RATS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZINES;

EID: 0035818920     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0109210     Document Type: Article

References (65)

1. Antidiabetic agents. Recent advances in their molecular and clinical pharmacology
2. Aldose reductase inhibitors and their potential for the treatment of diabetic complications
3. Diabetes complications and their potential prevention: Aldose reductase inhibition and other approaches
4. The role of aldose reductase in the development of diabetic complications
5. Aldose reductase inhibitors: Recent developments
6. Refined 1.8 Å structure of human aldose reductase complexed with the potent inhibitor zopolrestat
7. A "specificity" pocket inferred from the crystal structures of the complexes of aldose reductase with the pharmaceutically important inhibitors tolrestat and sorbinil
8. The alrestatin double-decker: Binding of two inhibitor molecules to human aldose reductase reveals a new specificity determinant
9. An anionic binding site in human aldose reductase: Mechanistic implications for the binding of citrate, cacodylate, and glucose-6-phosphate
10. A superfamily of NADPH-dependent reductases in eukaryotes and prokaryotes
11. Synthesis, activity, and molecular modeling of a new series of tricyclic pyridazinones as selective aldose reductase inhibitors
12. Peroxide-induced effects on lens cation transport following inhibition of glutathione reductase activity in vitro
13. Influence of the activity of glutathione reductase on the response of cultured lens epithelial cells from young and old rabbits to hydrogen peroxide
14. Aldose reductase inhibitors in the treatment of diabetic neuropathy. A review of the rationale and clinical evidence
15. 3-Aryl[1,2,4]triazino[4,3-a]benzimidazol-4(10H)-ones: Tricyclic heteroaromatic derivatives as a new class of benzodiazepine receptor ligands
16. 1 adenosine receptor antagonists
17. Einfache darstellung von N-substituierten isatinen
18. Benzazoles. 2-Hydrazino-and 2-azidobenzimidazoles
19. Condensation and ciclization reactions of 2-hydrazinobenzimidazole, -benzoxazole, and -benzothiazole
20. Cyclization of heterocyclic hydrazones prepared from dimethyl acetylenedicarboxylate
21. In vitro aldose reductase inhibitory activity of substituted N-benzenesulfonylglicyne derivatives
22. Novel inhibitors of rat lens aldose reductase: N-[[(substituted amino)phenyl]sulfonyl]glycines
23. 50 with bovine and rat lens extracts
24. Determination of AL01576 concentration in rat lenses and plasma by bioassay for aldose reductase activity measurements
25. Inhibition and activation studies on sheep liver sorbitol dehydrogenase
26. Ponalrestat, a potent and specific inhibitor of aldose reductase
27. 2,4-Dihydroxy benzylamine: A specific inhibitor of glutathione reductase
28. Prevention and reversal of galactose cataract in rats with topical sorbinil
29. N-[5-(trifluoromethyl)-6-methoxy- 1-naphthalenyl]thioxomethyl]-N-methylglycine (tolrestat), a potent, orally active aldose reductase inhibitor
30. A new approach against sugar cataract through aldose reductase inhibitors
31. Inhibition of human lens aldose reductase by flavonoids, sulindac and indomethacin
32. 2a and its isopropyl ester in vitro
33. Permeability of pilocarpic acid diesters across albino rabbit cornea in vitro
34. 2a prodrugs in rabbit cornea and conjunctiva
35. The protein data bank: A computer based archival file for macromolecular structures
36. An unlikely sugar substrate site in the 1.65 Å structure of the human aldose reductase holoenzyme implicated in diabetic complications
37. 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
38. Automated docking with grid-based energy evaluation
39. Orientational sampling and rigid-body minimization in molecular docking
40. Molecular modeling using shape descriptors
41. 1-antihistaminic agents
42. Synthesis, antilipidemic and platelet antiaggregatory activity of 2-aminobenzimidazole amide derivatives
43. A short synthesis of astemizole
44. Isolation and properties of lens aldose reductase
45. The MIDAS display system
46. Strategic approaches to drug design. 1. An integrated software framework for molecular modelling
47. AM1: A new general purpose mechanical molecular model
48. A second generation force field for the simulation of proteins, nucleic acids, and organic molecules
49. Molecular dynamics simulations of the structure of aldose reductase complexed with the inhibitor tolrestat
50. Tyrosine-48 is the proton donor and histidine-110 directs substrate stereochemical selectivity in the reduction reaction of human aldose reductase: Enzyme kinetics and crystal structure of the Y48H mutant enzyme
51. Catalytic mechanism of aldose reductase studied by the combined potentials of quantum mechanics and molecular mechanics
52. +/NADPH and alrestatin-like inhibitors
53. Aldose reductase as a target for drug design: Molecular modeling calculations on the binding of acyclic sugar substrates to the enzyme
54. An approach to computing electrostatic charges for molecules
55. A Broyden - Fletcher - Goldfarb - Shanno optimization procedure for molecular geometries
56. Solvent-accessible surfaces of proteins and nucleic acids
57. Analytical molecular surface calculation
58. Comparison of simple potential functions for simulating liquid water
59. Molecular dynamics with coupling to an external bath