Chiral resolution, determination of absolute configuration, and biological evaluation of (1,2-benzothiazin-4-yl)acetic acid enantiomers as aldose reductase inhibitors

References

• Van Heyningen R. Formation of polyols by the lens of the rat with ‘Sugar’ cataract. Nature 1959;184:194–5
   Web of Science ®Google Scholar
• Gabbay KH, Merola LO, Field RA. Sorbitol pathway: presence in nerve and cord with substrate accumulation in diabetes. Science 1966;151:209–10
   PubMed Web of Science ®Google Scholar
• Chung SSM, Chung SK. Genetic analysis of aldose reductase in diabetic complications. Curr Med Chem 2003;10:1375–87
   PubMed Web of Science ®Google Scholar
• Moczulski DK, Burak W, Doria A, et al. The role of aldose reductase gene in the susceptibility to diabetic nephropathy in Type II (non-insulin-dependent) diabetes mellitus. Diabetologia 1999;42:94–7
   PubMed Web of Science ®Google Scholar
• Kao YL, Donaghue K, Chan A, et al. A novel polymorphism in the aldose reductase gene promoter region is strongly associated with diabetic retinopathy in adolescents with type 1 diabetes. Diabetes 1999;48:1338–40
   PubMed Web of Science ®Google Scholar
• Kinoshita JH, Nishimura C. The involvement of aldose reductase in diabetic complications. Diabetes Metab Rev 1988;4:323–37
   PubMed Web of Science ®Google Scholar
• Ramirez MA, Borja NL. Epalrestat: an aldose reductase inhibitor for the treatment of diabetic neuropathy. Pharmacotherapy 2008;28:646–55
   PubMed Web of Science ®Google Scholar
• Chen X, Zhang SZ, Yang YC, et al. 1,2-Benzothiazine 1,1-dioxide carboxylate derivatives as novel potent inhibitors of aldose reductase. Bioorgan Med Chem 2011;19:7262–9
   PubMed Web of Science ®Google Scholar
• Fuji K. Asymmetric creation of quaternary carbon centers. Chem Rev 1993;93:2037–66
   Web of Science ®Google Scholar
• Mentel M, Blankenfeldt W, Breinbauer R. The active site of an enzyme can host both enantiomers of a racemic ligand simultaneously. Angew Chem Int Ed 2009;48:9084–7
   PubMed Web of Science ®Google Scholar
• Kasprzyk-Hordern B. Pharmacologically active compounds in the environment and their chirality. Chem Soc Rev 2010;39:4466–503
   PubMed Web of Science ®Google Scholar
• Carey JS, Laffan D, Thomson C, Williams MT. Analysis of the reactions used for the preparation of drug candidate molecules. Org Biomol Chem 2006;4:2337–47
   PubMed Web of Science ®Google Scholar
• Beck G. Synthesis of chiral drug substances. Synlett 2002;2002:837–50
   Google Scholar
• Costantino L, Rastelli G, Vianello P, et al. Diabetes complications and their potential prevention: Aldose reductase inhibition and other approaches. Med Res Rev 1999;19:3–23
   PubMed Web of Science ®Google Scholar
• Asano T, Saito Y, Kawakami M, et al. Fidarestat (SNK-860), a potent aldose reductase inhibitor, normalizes the elevated sorbitol accumulation in erythrocytes of diabetic patients. J Diabetes Complicat 2002;16:133–8
   PubMed Web of Science ®Google Scholar
• Negoro T, Murata P, Ueda S, et al. Novel, highly potent aldose reductase inhibitors: (R)-(−)-2-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydropyrrolo[1,2-alpha]pyrazine-4-spiro-3′-pyrrolidine-1,2′,3,5′-tetrone (AS-3201) and its congeners. J Med Chem 1998;41:4118–29
   PubMed Web of Science ®Google Scholar
• Hayman S, Kinoshita JH. Isolation and properties of lens aldose reductase. J Biol Chem 1965;240:877–82
   PubMed Web of Science ®Google Scholar
• La Motta C, Sartini S, Mugnaini L, et al. Pyrido[1,2-a]pyrimidin-4-one derivatives as a novel class of selective aldose reductase inhibitors exhibiting antioxidant activity. J Med Chem 2007;50:4917–27
   PubMed Web of Science ®Google Scholar
• Vine WH, Hsieh K-H, Marshall GR. Synthesis of fluorine-containing peptides. Analogs of angiotensin II containing hexafluorovaline. J Med Chem 1981;24:1043–7
   PubMed Web of Science ®Google Scholar
• Da Settimo F, Primofiore G, Da Settimo A, et al. Novel, highly potent aldose reductase inhibitors: cyano (2-oxo-2,3-dihydroindol-3-yl) acetic acid derivatives. J Med Chem 2003;46:1419–28
   PubMed Web of Science ®Google Scholar
• Kurono M, Kondo Y, Yamaguchi T, et al. Hydantoin derivatives for treating complications of diabetes. Google Patents; 1989
   Google Scholar
• Yabuuchi T, Kusumi T. Phenylglycine methyl ester, a useful tool for absolute configuration determination of various chiral carboxylic acids. J Org Chem 2000;65:397–404
   PubMed Web of Science ®Google Scholar
• El-Kabbani O, Wilson DK, Petrash M, Quiocho FA. Structural features of the aldose reductase and aldehyde reductase inhibitor-binding sites. Mol Vis 1998;4:19
   PubMedGoogle Scholar
• Ratliff DM, VanderJagt DJ, Eaton RP, VanderJagt DL. Increased levels of methylglyoxal-metabolizing enzymes in mononuclear and polymorphonuclear cells from insulin-dependent diabetic patients with diabetic complications: aldose reductase, glyoxalase I, and glyoxalase II – a clinical research center study. J Clin Endocr Metab 1996;81:488–92
   PubMed Web of Science ®Google Scholar
• Carper DA, Wistow G, Nishimura C, et al. A superfamily of nadph-dependent reductases in eukaryotes and prokaryotes. Exp Eye Res 1989;49:377–88
   PubMed Web of Science ®Google Scholar
• Sturm K, Levstik L, Demopoulos VJ, Kristl A. Permeability characteristics of novel aldose reductase inhibitors using rat jejunum in vitro. Eur J Pharm Sci 2006;28:128–33
   PubMed Web of Science ®Google Scholar