Discovery of [3-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyrrolo[2,3-b]pyridin-1-yl] acetic acids as highly potent and selective inhibitors of aldose reductase for treatment of chronic diabetic complications

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 7, 2009, Pages 2006-2008

  Van Zandt, Michael C ^a   Doan, Brian ^a   Sawicki, Diane R ^a   Sredy, Janet ^a   Podjarny, Alberto D ^b  

^a The Institute for Diabetes Discovery   (United States)

^b INSTITUT DE GÉNÉTIQUE ET DE BIOLOGIE MOLÉCULAIRE ET CELLULAIRE   (France)

Author keywords

Aldehyde reductase; Aldose reductase; Diabetes

Indexed keywords

[3 (4,5,7 TRIFLUOROBENZOTHIAZOL 2 YLMETHYL)PYRROLO[2,3 B]PYRIDIN 1 YL]ACETIC ACID; [6 METHYL 3 (4,5,7 TRIFLUOROBENZOTHIAZOL 2 YLMETHYL)PYRROLO[2,3 B]PYRIDIN 1 YL]ACETIC ACID; ALDEHYDE DERIVATIVE; ALDEHYDE REDUCTASE; ALDOSE REDUCTASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CHRONIC DISEASE; DETOXIFICATION; DIABETES MELLITUS; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; HYDROGEN BOND; IC 50; X RAY CRYSTALLOGRAPHY;

ACETIC ACIDS; ALDEHYDE REDUCTASE; BENZOTHIAZOLES; CATALYTIC DOMAIN; CHRONIC DISEASE; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; DIABETES COMPLICATIONS; ENZYME INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50;

TRIFLUORO;

EID: 62149150950     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.02.037     Document Type: Article

References (21)

1. Lorenzi M. Exp. Diabetes Res. (2007) 61038
2. In: Pickup J.C., and Williams G. (Eds). Textbook of Diabetes Vol. 1 (1997), Blackwell Science Ltd, United Kingdom Chapter 42
3. Williamson J.R., et al. Diabetes 42 (1993) 801
4. Setter S.M., Campbell R.K., and Cahoon C.J. Ann. Pharmacother. 37 (2003) 1858
5. Oates P.J. Curr. Drug Targets 9 (2008) 14
6. Ramirez M.A., and Borja N.L. Pharmacotherapy 28 (2008) 646
7. Hamada Y., and Nakamura J. Treatments Endocrinol. 3 (2004) 245
8. Shinoda M., Mori S., Shintani S., Ishikura S., and Hara A. Biol. Pharm. Bull. 22 (1999) 741
9. Suzuki K., Koh Y.H., Mizuno H., Hamaoka R., and Taniguchi N. J. Biochem. 123 (1998) 353
10. Bodreddigari S., Jones L.K., Egner P.A., Groopman J.D., Sutter C.H., Roebuck B.D., Guengerich F.P., Kensler T.W., and Sutter T.R. Chem. Res. Toxicol. 21 (2008) 1134
11. Takahashi M., Fujii J., Teshima T., Suzuki K., Shiba T., and Taniguchi N. Gene 127 (1993) 249
12. Kanazu T., Shinoda M., Nakayama T., Deyashiki Y., Hara A., and Sawada H. Biochem. J. 279 (1991) 903
13. Hamada Y., Araki N., Koh N., Nakamura J., Horiuchi S., and Hotta N. Biochem. Biophys. Res. Commun. 228 (1996) 539
14. Oya T., Hattori N., Mizuno Y., Miyata S., Maeda S., Osawa T., and Uchida K. J. Biol. Chem. 274 (1999) 18492
15. Cavalot F., Anfossi G., Russo I., Mularoni E., Massucco P., Mattiello L., Burzacca S., Hahn A., and Trovati M. Metabolism 45 (1996) 285
16. Fu M., Wells-Knecht K., Blackledge J., Lyons T., Thorpe S., and Baynes J. Diabetes 43 (1994) 676
17. Harrison D.H.T., Bohren K.M., Petsko G.A., Ringe D., and Gabbay K.H. Biochemistry 36 (1997) 16134
18. Van Zandt M.C., Jones M.L., Gunn D., Geraci L.S., Jones J.H., Sawicki D.R., Sredy J., Jacot J.L., DiCioccio A.T., Petrova T., Mitschler A., and Podjarny A.D. J. Med. Chem. 48 (2005) 3141
19. Van Zandt M.C., Sibley E.O., McCann E.E., Combs K.J., Flam B., Sawicki D., Sabetta A., Carrington A., Sredy J., Howard E., Mitschler A., Chevrier B., and Podjarny A. Bioorg. Med. Chem. 12 (2004) 5661
20. El-Kabbani O., and Podjarny A. Cell Mol. Life Sci. 15 (2007) 1970
21. Petrova T., Steuber H., Hazemann I., Cousido-Siah A., Mitschler A., Chung R., Oka M., Klebe G., El-Kabbani O., Joachimiak A., and Podjarney A. J. Med. Chem. 18 (2005) 5659