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Research Article

Design and synthesis of pyridazinone-substituted benzenesulphonylurea derivatives as anti-hyperglycaemic agents and inhibitors of aldose reductase – an enzyme embroiled in diabetic complications

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Pages 1415-1427 | Received 16 Dec 2015, Accepted 11 Jan 2016, Published online: 16 Feb 2016

References

  • Whiting DR, Guariguata L, Weil C, Shaw J. Global estimates of the prevalence of diabetes for 2011 and 2030. Diabetes Res Clin Pract 2011;94:311–21
  • Anjana RM, Pradeepa R, Deepa M, et al. ICMR-INDIAB collaborative study group: prevalence of diabetes and prediabetes (impaired fasting glucose and/or impaired glucose tolerance) in urban and rural India: phase I results of the Indian Council of Medical Research-India diabetes (ICMR-INDIAB) study. Diabetologia 2011;54:3022–7
  • Ferrannini E. Insulin resistance versus insulin deficiency in non-insulin-dependent diabetes mellitus: problems and prospects. Endocr Rev 1998;19:477–90
  • Lillioja S, Mott DM, Spraul M, et al. Insulin resistance and insulin secretory dysfunction as precursors of non-insulin-dependent diabetes mellitus: prospective studies of Pima Indians. Engl J Med 1993;329:1988–92
  • Sulman GI. Cellular mechanisms of insulin resistance. J Clin Invest 2000;106:171–6
  • Kahn SE. The relative contributions of insulin resistance and beta cell dysfunction to the pathophysiology of type 2 diabetes. Diabetologia 2003;46:3–19
  • LeRoith D. β-Cell dysfunction and insulin resistance in type 2 diabetes: role of metabolic and genetic abnormalities. Am J Med 2002;113:3–11
  • Robertson RP, Harmon J, Tran PO. Beta-cell glucose toxicity, lipotoxicity, and chronic oxidative stress in type 2 diabetes. Diabetes 2004;53:5119–24
  • Oates PJ. Polyol pathway and diabetic peripheral neuropathy. Int Rev Neurobiol 2002;50:325–92
  • Alexiou P, Pegklidou K, Chatzopoulou M, et al. Aldose reductase enzyme and its implication to major health problems of the 21(st) century. Curr Med Chem 2009;16:734–52
  • Jez JM, Bennett MJ, Schlegel BP, et al. Comparative anatomy of the aldo–keto reductase superfamily. Biochem J 1997;326:625–36
  • Vander Jagt DL, Kolb NS, Vander Jagt TJ, et al. Substrate specificity of human aldose reductase: identification of 4-hydroxynonenal as an endogenous substrate. Biochim Biophys Acta 1995;1249:117–26
  • Kumar PA, Reddy GB. Focus on molecules: aldose reductase. Exp Eye Res 2007;85:739–40
  • Peterson MJ, Sarges R, Aldinger CE, McDonald DP. CP-45,634: a novel aldose reductase inhibitor that inhibits polyol pathway activity in diabetic and galactosemic rats. Metab Clin Exp 1979;28:456–61
  • Kador FP, Kinoshita JH, Sharpless NE. Aldose reductase inhibitors: a potential new class of agents for the pharmacological control of certain diabetic complications. J Med Chem 1985;28:841–9
  • Carvalho VF, Barreto EO, Serra MF, et al. Aldose reductase inhibitor zopolrestat restores allergic hyporesponsiveness in alloxan-diabetic rats. Eur J Pharmacol 2006;549:173–8
  • (a) Settimo FD, Primofiore G, Motta CL, et al. Naphtho[1,2-d] isothiazole acetic acid derivatives as a novel class of selective aldose reductase inhibitors. J Med Chem 2005;48:6897–907 (b) El-Kabbani O, Carbone V, Darmanin C, et al. Structure of aldehyde reductase holoenzyme in complex with the potent aldose reductase inhibitor fidarestat:  implications for inhibitor binding and selectivity. J Med Chem 2005;48:5536–42 (c) Schemmel KE, Padiyara RS, D’Souza JJ. Aldose reductase inhibitors in the treatment of diabetic peripheral neuropathy: a review. J Diabetes Complicat 2010;24:354–60
  • Ramunno A, Cosconati S, Sartini S, et al. Progresses in the pursuit of aldose reductase inhibitors: the structure-based lead optimization step. Eur J Med Chem 2012;51:216–26
  • Donkora IO, Abdel-Ghanyb YS, Kadorc PF, et al. Synthesis and biological activities of aldose reductase inhibitors bearing acyl benzenesulfonamides as carboxylic acid surrogates. Eur J Med Chem 1998;33:15–22
  • Alexiou P, Demopoulos VJ. Novel inhibitors of rat lens aldose reductase: N-[[(substituted amino)phenyl]sulfonyl]glycines. J Med Chem 2010;53:7756–66
  • C. Zhu Aldose reductase inhibitors as potential therapeutic drugs of diabetic complications (Chapter 2). In: Oluwafemi O. Oguntibeju, ed. Diabetes mellitus – insights and perspectives. Croatia – European Union: INTECH; 2013:17–46
  • Kecskemeti V, Bagi Z, Posa I, et al. New trends in the development of oral antidiabetic drugs. Curr Med Chem 2002;9:53–71
  • Costantino L, Rastelli G, Vescovini K, et al. Synthesis, activity, and molecular modeling of a new series of tricyclic pyridazinones as selective aldose reductase inhibitors. J Med Chem 1996;39:4396–405
  • Costantino L, Rastelli G, Cignarella G, Barlocco D. Synthesis and aldose reductase inhibitory activity of a new series of benz[h]cinnolinone derivatives. Farmaco 2000;55:544–52
  • Courdert P, Duroux E, Bastide P, Couquelet J. Synthesis and evaluation of the aldose reductase inhibitory activity of new diaryl pyridazine-3-ones. J Pharm Belg 1991;46:375–80
  • Mylari BL, Armento SJ, Beebe DA, et al. A novel series of non-carboxylic acid, non-hydantoin inhibitors of aldose reductase with potent oral activity in diabetic rat models: 6-(5-chloro-3-methylbenzofuran-2-sulfonyl)-2H-pyridazin-3-one and congeners. J Med Chem 2005;48:6326–39
  • Srivastava BK, Joharapurkar A, Raval S, et al. Diaryl dihydropyrazole-3-carboxamides with significant in vivo antiobesity activity related to CB1 receptor antagonism:  synthesis, biological evaluation, and molecular modeling in the homology model. J Med Chem 2007;50:5951–66
  • LigPrep, Version 2.3, New York: Schrödinger, LLC; 2009
  • Glide, Version 5.5, New York: Schrödinger, LLC; 2009
  • Suryanarayana P, Kumar PA, Saraswat M, et al. Inhibition of aldose reductase by tannoid principles of Emblica officinalis: implications for the prevention of sugar cataract. Mol Vis 2004;10:148–54
  • Yaseen R, Ekinci D, Senturk M, et al. Pyridazinone substituted benzenesulfonamides as potent carbonic anhydrase inhibitors. Bioorg Med Chem Lett. [Epub ahead of print]. doi:10.1016/j.bmcl.2015.12.016
  • Bohren KM, Grimshaw CE, Lai CJ, et al. 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. Biochemistry 1994;33:2021–32
  • Grimshaw CE, Bohren KM, Lai CJ, Gabbay KH. Human aldose reductase: pK of tyrosine 48 reveals the preferred ionization state for catalysis and inhibition. Biochemistry 1995;34:14374–84

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