Design and synthesis of N-(3,5-difluoro-4-hydroxyphenyl)benzenesulfonamides as aldose reductase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 7, 2008, Pages 3926-3932

  Alexiou, Polyxeni ^a   Nicolaou, Ioannis ^a   Stefek, Milan ^b   Kristl, Albin ^c   Demopoulos, Vassilis J ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^b INSTITUTE OF EXPERIMENTAL PHARMACOLOGY AND TOXICOLOGY   (Slovakia)

^c UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

Antidiabetic aldose reductase inhibitors; Antioxidant activity; Non classical bioisosterism; Permeability

Indexed keywords

4 AMINO N(3,5 DIFLUORO 4 HYDROXYPHENYL)BENZENESULFONAMIDE; ALDOSE REDUCTASE INHIBITOR; N (3,5 DIFLUORO 4 HYDROXYPHENYL) 4 METHOXYBENZENESULFONAMIDE; N (3,5 DIFLUORO 4 HYDROXYPHENYL) 4 NITROBENZENESULFONAMIDE; N (3,5 DIFLUORO 4 HYDROXYPHENYL)BENZENESULFONAMIDE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; DRUG ACTIVITY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; INTESTINE MUCOSA PERMEABILITY; NONHUMAN; RAT;

ALDEHYDE REDUCTASE; ANIMALS; ANTIOXIDANTS; BIPHENYL COMPOUNDS; DRUG DESIGN; ENZYME INHIBITORS; EYE; FEMALE; FLUORINE COMPOUNDS; HYDRAZINES; HYDROXYLATION; JEJUNUM; LIPID PEROXIDATION; MALE; MOLECULAR STRUCTURE; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 41649105654     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.01.042     Document Type: Article

References (44)

1. Zimmet P., Alberti K.G.M.M., and Show J. Nature 414 (2001) 782
2. Fracchiolla G., Laghezza A., Piemontese L., Carbonara G., Lavecchia A., Tortorella P., Crestani M., Novellino E., and Loiodice F. ChemMedChem 2 (2007) 641
3. Diamond J. Nature 423 (2003) 599
4. Fujisawa T., Ikegami H., Kawaguchi Y., Nojima K., Kawabata Y., Ono M., Nishino M., Noso S., Taniguchi H., Horiki M., Itoi-Babaya M., Babaya N., Inoue K., and Ogihata T. Diabetes Res. Clin. Pract. 66S (2004) S91
5. Miyamoto S. Chem. Biol. Inform. J. 2 (2002) 74
6. Ziegler D. Nephrol. Dial. Transplant. 19 (2004) 2170
7. Carrington A.L., and Litchfield J.E. Diabetes Rev. 7 (1999) 275
8. Sheet M.J., and King G.L. JAMA J. Am. Med. Assoc. 288 (2002) 2579
9. Miyamoto S. Expert Opin. Ther. Pat. 12 (2002) 621
10. Sturm K., Levstik L., Demopoulos V.J., and Kristl A. Eur. J. Pharm. Sci. 28 (2006) 128
11. Nicolaou I., Zika C., and Demopoulos V.J. J. Med. Chem. 47 (2004) 2706
12. Mylari B.L., Armento S.J., Beebe D.A., Conn E.L., Coutcher J.B., Dina M.S., O'Gorman M.T., Linhares M.C., Martin W.H., Oates P.J., Tess D.A., Withbroe G.J., and Zembrowski W.J. J. Med. Chem. 48 (2005) 6326
13. De Ruiter J., Brubaker A.N., Garner M.A., Barksdale J.M., and Mayfield C.A. J. Pharm. Sci. 76 (1987) 149
14. Qiu J., Stevenson S.H., O'Beirne M.J., and Silverman R.B. J. Med. Chem. 42 (1999) 329
15. Alexidis A.N., Rekka E.A., Demopoulos V.J., and Kourounakis P.N. J. Pharm. Pharmacol. 47 (1995) 131
16. 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., and Le Ridant A. Free Radical Biol. Med. 25 (1998) 113
17. Molyneux P. Songklanakarin J. Sci. Technol. 26 (2004) 211
18. Rackova L., Snirc V., Majekova M., Majek P., and Stefek M. J. Med. Chem. 49 (2006) 2543
19. Rackova L., Stefek M., and Majekova M. Redox Rep. 7 (2002) 207
20. Constantino L., Rastelli G., Gamberini M.C., Vinson J.A., Bose P., Iannone A., Staffieri M., Antolini L., Del Corso A., Mura U., and Albasini A. J. Med. Chem. 42 (1999) 1881
21. Basile-Doelsch I., Meunier J.D., and Parron C. Nature 433 (2005) 399
22. Grondal C. Synlett 10 (2003) 1568
23. Murugan R., and Scriven E.F.V. Aldrichim. Acta 36 (2003) 21
24. Demopoulos V.J., Nicolaou I., and Zika C. Chem. Pharm. Bull. 51 (2003) 98
25. Gui T., Tanimoto T., Kokai Y., and Nishimura C. Eur. J. Biochem. 227 (1995) 448
26. Del Corso A., Costantino L., Rastelli G., Buono F., and Mura U. Exp. Eye Res. 71 (2000) 515
27. Gillespie P., and Goodnow Jr. R.A. Annu. Rep. Med. Chem. 39 (2004) 293
28. SPARTAN SGI, version 5.1.3 OpenGL; Wavefunction Inc., 18401 Von Karman Avenue, Suite 370, Irvine, CA 92612.
29. Kador P.F., Kinoshita J.H., and Sharpless N.E. J. Med. Chem. 28 (1985) 841
30. Kissinger C.R., Turley S., and Clark J.I. Acta Cryst. C44 (1988) 512
31. Buyukbingol E., and Klopman G. J. Math. Chem. 8 (1991) 195
32. Ishida T., In Y., Tanaka C., and Inoue M. Acta Cryst. B47 (1991) 806
33. Nicolaou I., and Demopoulos V.J. J. Med. Chem. 46 (2003) 417
34. Blois M.S. Nature 181 (1958) 1199
35. Lehuede J., Fauconneau B., Barrier L., Ourakow M., Piriou A., and Vierfond J.-M. Eur. J. Med. Chem. 34 (1999) 991
36. Silva J., Areias F.M., Proenca F.M., and Coutinho O.P. Life Sci. 78 (2006) 1256
37. Castro I., Rogero M., Junqueira R., and Carrapeiro M. Int. J. Food Sci. Nutr. 57 (2006) 75
38. Bondet V., Brand-Williams W., and Berset C. LWT Food Sci. Technol. 30 (1997) 609
39. U.S. Department of Health and Human Services. BP.U.S. Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research (CDER). 2000.
40. Polli J.E., Yu L.X., Cook J.A., Amidon G.L., Borchardt R.T., Burnside B.A., Burton P.S., Chen M.L., Conner D.P., Faustino P.J., Hawi A.A., Hussain A.S., Joshi H.N., Kwei G., Lee V.H., Lesko L.J., Lipper R.A., Loper A.E., Nerurkar S.G., Polli J.W., Sanvorde R., Taneja R.S., Uppoor C., Vattikonda S., Wilding I., and Zhang G. J. Pharm. Sci. 93 (2004) 1375
41. Lennernäs H. J. Pharm. Sci. 87 (1998) 403
42. Matsuda H., Wang T., Managi H., and Yoshikawa M. Bioorg. Med. Chem. 11 (2003) 5317
43. Mihaljevic B., Katusin-Razem B., and Razem D. Free Radical Biol. Med. 21 (1996) 53
44. Zaher N., Nicolaou I., and Demopoulos V.J. J. Enzyme Inhib. Med. Chem. 17 (2002) 131