A diverse series of substituted benzenesulfonamides as aldose reductase inhibitors with antioxidant activity: Design, synthesis, and in vitro activity

Journal of Medicinal Chemistry

Volumn 53, Issue 21, 2010, Pages 7756-7766

  Alexiou, Polyxeni ^a   Demopoulos, Vassilis J ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 2 (PHENYLSULFONAMIDO)ACETIC ACID; 2,6 DIFLUOROPHENOL; 4 AMINO N (4 BROMO 2 FLUOROBENZYL) N (3,5 DIFLUORO 4 HYDROXYPHENYL)BENZENESULFONAMIDE; 4 BROMO 2 FLUOROBENZYL; ALDEHYDE REDUCTASE; ALDOSE REDUCTASE INHIBITOR; BENZENESULFONAMIDE DERIVATIVE; BENZYL DERIVATIVE; ISOXAZOLIDIN 3 ONE PHENYLSULFONAMIDE DERIVATIVE; METHYLSULFONYLAMIDE; N (1H TETRAZOL 5 YL)BENZENESULFONAMIDE; N (3,5 DIFLUORO 4 HYDROXYPHENYL) 4 (1H PYRROL 1 YL)BENZENESULFONAMIDE; N (3,5 DIFLUORO 4 HYDROXYPHENYL) 4 (3 ETHYLUREIDO)BENZENESULFONAMIDE; N (3,5 DIFLUORO 4 HYDROXYPHENYL) 4 (TRIFLUOROMETHYL)BENZENESULFONAMIDE; N (3,5 DIFLUORO 4 HYDROXYPHENYL) N (PHENYLSULFONYL)BENZENESULFONAMIDE; N (3,5 DIFLUORO 4 HYDROXYPHENYL)BENZENESULFONAMIDE; N (3,5 DIFLUORO 4 HYDROXYPHENYL)BENZENESULFONAMIDE DERIVATIVE; N (4 BROMO 2 FLUOROBENZYL) N (3,5 DIFLUORO 4 HYDROXYPHENYL) 4 NITROBENZENESULFONAMIDE; N (4 BROMO 2 FLUOROBENZYL) N (3,5 DIFLUORO 4 HYDROXYPHENYL)ARYLSULFONAMIDE; N (4 BROMO 2 FLUOROBENZYL) N (3,5 DIFLUORO 4 HYDROXYPHENYL)BENZENESULFONAMIDE; N (METHYLSULFONYL) 2 (PHENYLSULFONAMIDO)ACETAMIDE; N [4 [N (3,5 DIFLUORO 4 HYDROXYPHENYL)SULFAMOYL]PHENYL]4 METHOXYBENZAMIDE; N [4 [N (3,5 DIFLUORO 4 HYDROXYPHENYL)SULFAMOYL]PHENYL]BENZAMIDE; PHENOL DERIVATIVE; PHENYLSULFONAMIDODIFLUOROPHENOL; SULFAMOYLPHENYLBENZAMIDE; SULFANILAMIDE; SULFONAMIDE; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; DRUG DESIGN; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVATION; FEMALE; IC 50; LIPID PEROXIDATION; MALE; NONHUMAN; RAT; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

ALDEHYDE REDUCTASE; ANIMALS; ANTIOXIDANTS; BENZENE DERIVATIVES; DRUG DESIGN; FEMALE; FREE RADICAL SCAVENGERS; LIPID PEROXIDATION; MALE; RATS; RATS, INBRED F344; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 78149239485     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101008m     Document Type: Article

References (61)

1. Demopoulos, V. J.; Zaher, N.; Zika, C.; Anagnostou, C.; Mamadou, E.; Alexiou, P.; Nicolaou, I. Compounds that combine aldose reductase inhibitory activity and ability to prevent the glycation (glucation and/or fructation) of proteins as putative pharmacotherapeutic agents Drug Design Reviews Online 2005, 2, 293-304
2. Alexiou, P.; Pegklidou, K.; Chatzopoulou, M.; Nicolaou, I.; Demopoulos, V. J. Aldose reductase enzyme and its implication to major health problems of the 21(st) century Curr. Med. Chem. 2009, 16, 734-752
3. Ramirez, M. A.; Borja, N. L. Epalrestat: an aldose reductase inhibitor for the treatment of diabetic neuropathy Pharmacotherapy 2008, 28, 646-655
4. Schemmel, K. E.; Padiyara, R. S.; D'Souza, J. J. Aldose reductase inhibitors in the treatment of diabetic peripheral neuropathy: a review J. Diabetes Complications 2010, 24, 354-360
5. Alexiou, P.; Nicolaou, I.; Stefek, M.; Kristl, A.; Demopoulos, V. J. Design and synthesis of N -(3,5-difluoro-4-hydroxyphenyl)benzenesulfonamides as aldose reductase inhibitors Bioorg. Med. Chem. 2008, 16, 3926-3932 (Pubitemid 351484026)
6. Sturm, K.; Levstik, L.; Demopoulos, V. J.; Kristl, A. Permeability characteristics of novel aldose reductase inhibitors using rat jejunum in vitro Eur. J. Pharm. Sci. 2006, 28, 128-133
7. Lima, L. M. A.; Barreiro, E. J. Bioisosterism: a useful strategy for molecular modification and drug design Curr. Med. Chem. 2005, 12, 23-49
8. Wagener, M.; Lommerse, J. P. M. The quest for bioisosteric replacements J. Chem. Inf. Model. 2006, 46, 677-685
9. Reitz, A. B.; Smith, G. R.; Parker, M. H. The role of sulfamide derivatives in medicinal chemistry: a patent review (2006-2008) Expert Opin. Ther. Pat. 2009, 19, 1449-1453
10. DeRuiter, 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
11. DeRuiter, J.; Mayfield, C. A. Inhibitory activity and mechanism of inhibition of the N -[[(4-benzoylamino)phenyl]sulfonyl]amino acid aldose reductase inhibitors Biochem. Pharmacol. 1990, 40, 2219-2226
12. Mayfield, C. A.; DeRuiter, J. Novel inhibitors of rat lens aldose reductase: N -[[(substituted amino)phenyl]sulfonyl]glycines J. Med. Chem. 1987, 30, 1595-1598
13. Yuan, H.; Silverman, R. B. New substrates and inhibitors of gamma-aminobutyric acid aminotransferase containing bioisosteres of the carboxylic acid group: design, synthesis, and biological activity Bioorg. Med. Chem. 2006, 14, 1331-1338
14. Qiu, J.; Stevenson, S. H.; O'Beirne, M. J.; Silverman, R. B. 2,6-Difluorophenol as a bioisostere of a carboxylic acid: bioisosteric analogues of gamma-aminobutyric acid J. Med. Chem. 1999, 42, 329-332
15. Nicolaou, L.; Zika, C.; Demopoulos, V. J. [1-(3,5-Difluoro-4- hydroxyphenyl)-1 H -pyrrol-3-yl]phenylmethanone as a bioisostere of a carboxylic acid aldose reductase inhibitor J. Med. Chem. 2004, 47, 2706-2709
16. Pallas, version 3.3.2.4; CompuDrug Chemistry Ltd.: Sedona, AZ, 1994, and 2006.
17. Kador, P. F.; Goosey, J. D.; Sharpless, N. E.; Kolish, J.; Miller, D. D. Stereospecific inhibition of aldose reductase EC-1.1.1.21 Eur. J. Med. Chem. 1981, 16, 293-298
18. El-Kabbani, O.; Darmanin, C.; Oka, M.; Schulze-Briese, C.; Tomizaki, T.; Hazemann, I.; Mitschler, A.; Podjarny, A. High-resolution structures of human aldose reductase holoenzyme in complex with stereoisomers of the potent inhibitor fidarestat: stereospecific interaction between the enzyme and a cyclic imide type inhibitor J. Med. Chem. 2004, 47, 4530-4537
19. El-Kabbani, O.; Carbone, V.; Darmanin, C.; Oka, M.; Mitschler, A.; Podjarny, A.; Schulze-Briese, C.; Chung, R. P. Structure of aldehyde reductase holoenzyme in complex with the potent aldose reductase inhibitor fidarestat: implications for inhibitor binding and selectivity J. Med. Chem. 2005, 48, 5536-5542 (Pubitemid 41209251)
20. Kurono, M.; Fujiwara, I.; Yoshida, K. Stereospecific interaction of a novel spirosuccinimide type aldose reductase inhibitor, AS-3201, with aldose reductase Biochemistry 2001, 40, 8216-8226
21. Negoro, T.; Murata, M.; Ueda, S.; Fujitani, B.; Ono, Y.; Kuromiya, A.; Komiya, M.; Suzuki, K.; Matsumoto, J. Novel, highly potent aldose reductase inhibitors: (R)-(-)-2-(4-bromo-2-fluorobenzyl)-1,2,3,4- tetrahydropyrrolo[1,2 - A ]pyrazine -4-spiro-3'-pyrrolidine-1,2',3,5'-tetrone (AS-3201) and its congeners J. Med. Chem. 1998, 41, 4118-4129
22. Rakowitz, D.; Gmeiner, A.; Schroder, N.; Matuszczak, B. Synthesis of novel phenylacetic acid derivatives with halogenated benzyl subunit and evaluation as aldose reductase inhibitors Eur. J. Pharm. Sci. 2006, 27, 188-193
23. Kirk, K. L. Selective fluorination in drug design and development: an overview of biochemical rationales Curr. Top. Med. Chem. 2006, 6, 1447-1456
24. Duarte, C. D.; Barreiro, E. J.; Fraga, C. A. M. Privileged structures: a useful concept for the rational design of new lead drug candidates Mini-Rev. Med. Chem. 2007, 7, 1108-1119
25. El-Kabbani, O.; Old, S. E.; Ginell, S. L.; Carper, D. A. Aldose and aldehyde reductases: structure-function studies on the coenzyme and inhibitor-binding sites Mol. Vision 1999, 5, 20-26
26. El-Kabbani, O.; Podjarny, A. Selectivity determinants of the aldose and aldehyde reductase inhibitor-binding sites Cell. Mol. Life Sci. 2007, 64, 1970-1978
27. Cappiello, M.; Voltarelli, M.; Cecconi, I.; Vilardo, P. G.; Dal Monte, M.; Marini, I.; Del Corso, A.; Wilson, D. K.; Quiocho, F. A.; Petrash, J. M.; Mura, U. Specifically targeted modification of human aldose reductase by physiological disulfides J. Biol. Chem. 1996, 271, 33539-33544
28. Grimshaw, C. E.; Lai, C.-J. Oxidized aldose reductase: in vivo factor, not in vitro artifact Arch. Biochem. Biophys. 1996, 327, 89-97
29. Srivastava, S. K.; Ramana, K. V.; Bhatnagar, A. Role of aldose reductase and oxidative damage in diabetes and the consequent potential for therapeutic options Endocr. Rev. 2005, 26, 380-392
30. Peet, N. P.; Sunder, S.; Barbuch, R. J.; Huber, E. W.; Bargar, E. M. Sulfonylcarbamimidic azides from sulfonyl chlorides and 5-aminotetrazole J. Heterocycl. Chem. 1987, 24, 1531-1535
31. Buckman, B. O.; Morrissey, M. M.; Mohan, R. Solution-phase parallel synthesis of benzoxazines using a polymer-supported carbodiimide Tetrahedron Lett. 1998, 39, 1487-1488
32. Belousova, I. A.; Simanenko, Y. S.; Savelova, V. A.; Suprun, I. P. Mechanism of catalysis with triethylamine of phenols benzoylation in dioxane. New quality experiment Russ. J. Org. Chem. 2000, 36, 1656-1664
33. DeRuiter, J.; Borne, R. F.; Mayfield, C. A. N- and 2-substituted N-(phenylsulfonyl)glycines as inhibitors of rat lens aldose reductase J. Med. Chem. 1989, 32, 145-151
34. Yasuhara, A.; Kameda, M.; Sakamoto, T. Selective monodesulfonylation of N, N -disulfonylarylamines with tetrabutylammonium fluoride Chem. Pharm. Bull. 1999, 47, 809-812
35. Wittenberger, S. J.; Donner, B. G. Dialkyltin oxide-mediated addition of trimethylsilyl azide to nitriles: a novel preparation of 5-substituted tetrazoles J. Org. Chem. 1993, 58, 4139-4141
36. Malspeis, L.; Gold, D. Stability of cycloserine in buffered aqueous solutions J. Pharm. Sci. 1964, 53, 1173-1179
37. Gui, T.; Tanimoto, T.; Kokai, Y.; Nishimura, C. Presence of a closely related subgroup in the aldo-ketoreductase family of the mouse Eur. J. Biochem. 1995, 227, 448-453
38. Del Corso, A.; Costantino, L.; Rastelli, G.; Buono, F.; Mura, U. Aldose reductase does catalyse the reduction of glyceraldehyde through a stoichiometric oxidation of NADPH Exp. Eye Res. 2000, 71, 515-521
39. Demopoulos, V. J.; Rekka, E. Isomeric benzoylpyrroleacetic acids: some structural aspects for aldose reductase inhibitory and anti-inflammatory activities J. Pharm. Sci. 1995, 84, 79-82
40. Kador, P. F.; Sharpless, N. E. Pharmacophor requirements of the aldose reductase inhibitor site Mol. Pharmacol. 1983, 24, 521-531
41. Kador, P. F.; Lee, Y. S.; Rodriguez, L.; Sato, S.; Bartoszko-Malik, A.; Abdel-Ghany, Y. S.; Miller, D. D. Identification of an aldose reductase inhibitor site by affinity labeling Bioorg. Med. Chem. 1995, 3, 1313-1324
42. El-Kabbani, O.; Wilson, D. K.; Petrash, M.; Quiocho, F. A. Structural features of the aldose reductase and aldehyde reductase inhibitor-binding sites Mol. Vision 1998, 4, 19-26
43. Steuber, H.; Heine, A.; Podjarny, A.; Klebe, G. Merging the binding sites of aldose and aldehyde reductase for detection of inhibitor selectivity-determining features J. Mol. Biol. 2008, 379, 991-1016
44. Pegklidou, K.; Koukoulitsa, C.; Nicolaou, I.; Demopoulos, V. J. Design and synthesis of novel series of pyrrole based chemotypes and their evaluation as selective aldose reductase inhibitors. A case of bioisosterism between a carboxylic acid moiety and that of a tetrazole Bioorg. Med. Chem. 2010, 18, 2107-2114
45. Feather, M. S.; Geoffrey Flynn, T.; Munro, K. A.; Kubiseski, T. J.; Walton, D. J. Catalysis of reduction of carbohydrate 2-oxoaldehydes (osones) by mammalian aldose reductase and aldehyde reductase Biochim. Biophys. Acta 1995, 1244, 10-16
46. Suzuki, K.; Koh, Y. H.; Mizuno, H.; Hamaoka, R.; Taniguchi, N. Overexpression of aldehyde reductase protects PC12 cells from the cytotoxicity of methylglyoxal or 3-deoxyglucosone J. Biochem. 1998, 123, 353-357
47. Shinohara, M.; Thornalley, P. J.; Giardino, I.; Beisswenger, P.; Thorpe, S. R.; Onorato, J.; Brownlee, M. Overexpression of glyoxalase-I in bovine endothelial cells inhibits intracellular advanced glycation endproduct formation and prevents hyperglycemia-induced increases in macromolecular endocytosis J. Clin. Invest. 1998, 101, 1142-1147
48. Vander Jagt, D. L.; Hunsaker, L. A. Methylglyoxal metabolism and diabetic complications: roles of aldose reductase, glyoxalase-I, betaine aldehyde dehydrogenase and 2-oxoaldehyde dehydrogenase Chem.-Biol. Interact. 2003, 143-144, 341-351
49. Carbone, V.; Hara, A.; El-Kabbani, O. Structural and functional features of dimeric dihydrodiol dehydrogenase Cell. Mol. Life Sci. 2008, 65, 1464-1474
50. Sato, K.; Inazu, A.; Yamaguchi, S.; Nakayama, T.; Deyashiki, Y.; Sawada, H.; Hara, A. Monkey 3-deoxyglucosone reductase: tissue distribution and purification of three multiple forms of the kidney enzyme that are identical with dihydrodiol dehydrogenase, aldehyde reductase, and aldose reductase Arch. Biochem. Biophys. 1993, 307, 286-294
51. Sato, S. Rat kidney aldose reductase and aldehyde reductase and polyol production in rat kidney Am. J. Physiol. 1992, 263, F799-F805
52. Terubayashi, H.; Sato, S.; Nishimura, C.; Kador, P. F.; Kinoshita, J. H. Localization of aldose and aldehyde reductase in the kidney Kidney Int. 1989, 36, 843-851
53. Molyneux, P. The use of the stable free radical diphenylpicryl-hydrazyl (DPPH) for estimating antioxidant activity Songklanakarin J. Sci. Technol. 2004, 26, 211-219
54. Silva, J. P.; Areias, F. M.; Proenca, F. M.; Coutinho, O. P. Oxidative stress protection by newly synthesized nitrogen compounds with pharmacological potential Life Sci. 2006, 78, 1256-1267
55. Bondet, V.; Brand-Williams, W.; Berset, C. Kinetics and mechanisms of antioxidant activity using the DPPH free radical method Lebensm.-Wiss. Technol. 1997, 30, 609-615
56. Toko, H. Advanced Free Radical Reactions for Organic Synthesis; Elsevier: Amsterdam, 2004.
57. Ancerewicz, J.; Migliavacca, E.; Carrupt, P. A.; Testa, B.; Bree, F.; Zini, R.; Tillement, J. P.; Labidalle, S.; Guyot, D.; Chauvet-Monges, A. M.; Crevat, A.; Le Ridant, A. Structure-property relationships of trimetazidine derivatives and model compounds as potential antioxidants Free Radical Biol. Med. 1998, 25, 113-120
58. Stefek, M.; Snirc, V.; Djoubissie, P. O.; Majekova, M.; Demopoulos, V.; Rackova, L.; Bezakova, Z.; Karasu, C.; Carbone, V.; El-Kabbani, O. Carboxymethylated pyridoindole antioxidants as aldose reductase inhibitors: synthesis, activity, partitioning, and molecular modeling Bioorg. Med. Chem. 2008, 16, 4908-4920
59. Bengelsdorf, I. S. A reaction of guanidine with glyoxals in aqueous solution. The preparation of glycocyamidines J. Am. Chem. Soc. 1953, 75, 3138-3140
60. Dahlbom, R. Phenyl- and tolylsulfonyl derivatives of heterocyclic amines Sven. Kem. Tidskr. 1943, 55, 122-125
61. Chatterjee, S. N.; Agarwal, S. Liposomes as membrane model for study of lipid peroxidation Free Radical Biol. Med. 1988, 4, 51-72