Design, Synthesis and Pharmacological Evaluation of R/S-3,4-Dihydro-2,2-Dimethyl-6-Halo-4-(Phenylaminocarbonylamino)-2H-1-Benzopyrans: Towards Tissue-Selective Pancreatic Beta-Cells KATP Channel Openers Structually Related to (+/-)-Cromakalim
Sebille, S.; Gall, D.; De Tullio, Pascalet al.
2006 • In Journal of Medicinal Chemistry, 49, p. 4690-4697
De Tullio, Pascal ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Florence, Xavier ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Lebrun, P.
Pirotte, Bernard ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Language :
English
Title :
Design, Synthesis and Pharmacological Evaluation of R/S-3,4-Dihydro-2,2-Dimethyl-6-Halo-4-(Phenylaminocarbonylamino)-2H-1-Benzopyrans: Towards Tissue-Selective Pancreatic Beta-Cells KATP Channel Openers Structually Related to (+/-)-Cromakalim
Publication date :
2006
Journal title :
Journal of Medicinal Chemistry
ISSN :
0022-2623
eISSN :
1520-4804
Publisher :
American Chemical Society, Washington, United States - District of Columbia
Cook, D. L.; Hales, C. N. Intracellular ATP directly blocks K+ channels in pancreatic B-cells. Nature 1984, 311, 271-273.
Spruce, A. E.; Standen, N. B.; Stanfield, P. R. Voltage-dependent ATP-sensitive potassium channels of skeletal muscle membrane. Nature 1985, 316, 736-738.
Standen, N. B.; Quayle, J. M.; Davies, N. W.; Brayden, J. E.; Huang, Y.; Nelson, M. T. Hyperpolarizing vasodilators activate ATP-sensitive K+ channels in arterial smooth muscle. Science 1989, 245, 177-180.
Noma, A. ATP-regulated K+ channels in cardiac muscle. Nature 1983, 305, 147-148.
Bernardi, H.; Fosset, M.; Lazdunski, M. Characterization, purification and affinity labeling of the brain [3H] glibenclamide-binding protein, a putative neuronal ATP-regulated K+ channel. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 9816-9820.
Pirotte, B.; Fontaine, J.; Lebrun, P. Recent advances in the chemistry of potassium channel openers. Curr. Med. Chem. 1995, 2, 573-582.
Seino S. ATP-sensitive potassium channels: a model of heteromultimeric potassium channel/receptor assemblies. Annu. Rev. Physiol. 1999, 61, 337-362.
Inagaki, N.; Gonio, T.; Clement, J. P. Reconstitution of I KATP: an inward rectifier subunit plus a sulfonylurea receptor. Science 1995, 270, 1166-1170.
Hambrock, A.; Löfter-Walz, C.; Delabar, U.; Horio, Y.; Kurachi, Y.; Quast, U. ATP-sensitive K+ channel modulators binding to sulfonylurea receptors SUR2A and SUR2B: opposite effects of MgADP. Mol. Pharmacol. 1999, 55, 832-840.
Lawson, K. Potassium channel activation: a potential therapeutic approach? Pharmacol. Ther. 1996, 70, 39-63.
Robertson, D. W.; Steinberg, M. I. Potassium channel modulators: scientific applications and therapeutic promise. J. Med. Chem. 1990, 33, 1529-1541.
Björk, E.; Berne, C.; Kämpe, O.; Wibell, P.; Oskarsson, P.; Karlsson, F. A. Diazoxide treatment at onset preserves residual insulin secretion in adults with autoimmune diabetes. Diabetes 1996, 45, 1427-1430.
Alemzadeh, R.; Langley, G.; Upchurch, L.; Smith, P.; Slonim, A. E. Beneficial effect of diazoxide in obese hyperinsulinemic adults. J. Clin. Endocrinol. Metab. 1998, 83, 1911-1915.
Rasmussen, S. B.; Sorensen, T. S.; Hansen, J. B.; Mandrup-Poulsen, T.; Hornum, L.; Markholst, H. Functional rest through intensive treatment with insulin and potassium channel openers preserves residual beta-cells function and mass in acutely diabetic BB rats. Horm. Metab. Res. 2000, 32, 294-300.
Cosgrove, K.; Antoine, M.-H.; Lee, A.; Barnes, P.; de Tullio, P.; Clayton, P.; McCloy, R.; De Lonlay, P.; Nihoul-Fékété, C.; Robert, J.; Saudubray, J.-M.; Rahier, J.; Lindley, K.; Hussain, K.; Aynsley-Green, A.; Pirotte, B.; Lebrun, P.; Dunne, M. BPDZ 154 activates adenosine 5′-triphosphate-sensitive potassium channels: in vitro studies using rodent insulin-secreting cells and islets isolated from patients with hyperinsulinism. J. Clin. Endocrinol. Metab. 2002, 87, 4860-4868.
Mannhold, R. KATP channel openers: structure-activity relationships and therapeutic potential. Med. Res. Rev. 2004, 24, 213-266.
Hamilton, T. C.; Weir, S. W.; Weston, A. H. Comparison of the effects of BRL 34915 and verapamil on electrical and mechanical activity in rat portal vein. Br. J. Pharmacol. 1986, 88, 103-111.
Petit, P.; Hillaire-Buys, D.; Mir, A.-K.; Loubatieres-Mariani, M.-M. Differential effects of cromakalim on pancreatic vascular resistance and insulin secretion in vitro. Fundam. Clin. Pharmacol. 1992, 6, 185-190.
Lebrun, P.; Antoine, M.-H.; Devreux, V.; Hermann, M.; Herchuelz, A. Paradoxical inhibitory effect of cromakalim on 86Rb outflow from pancreatic islets cells. J. Pharmacol. Exp. Ther. 1990, 255, 948-954.
Lebrun, P.; Arkhammar, P.; Antoine, M.-H.; Nguyen, Q.-A.; Hansen, J. B.; Pirotte, B. A potent diazoxide analogue activating ATP-sensitive K+ channels and inhibiting insulin release. Diabetologia 2000, 43, 723-732.
Sebille, S.; de Tullio, P.; Becker, B.; Antoine, M.-H.; Boverie, S.; Pirotte, B.; Lebrun, P. 4,6-Disubstituted 2,2-dimethylchromans structurally related to the KATP channel opener cromakalim: design, synthesis and effect on insulin release and vascular tone. J. Med. Chem, 2005, 48, 614-621.
Khelili, S.; Nguyen, Q.-A.; Lebrun, P.; Delarge, J.; Pirotte, B. Synthesis and pharmacological evaluation of KATP-channel openers related to cromakalim: introduction of arylsulfonylurea moieties. Pharm. Pharmacol. Commun. 1999, 5, 189-193.
Henning, R.; Lattrell, R.; Gerhards, H. J.; Leven, M. Synthesis and neuroleptic activity of a series of 1-[1-(benzo-1,4-dioxan-2-ylmethyl)-4- piperidinyl]benzimidazolone derivatives. J. Med. Chem. 1987, 30, 814-819.
de Tullio, P.; Becker, B.; Boverie, S.; Dabrowski, M.; Wahl, P.; Antoine, M.-H.; Somers, F.; Sebille, S.; Ouedraogo, R.; Hansen, J. B.; Lebrun, P.; Pirotte, B. Towards tissue-selective pancreatic B-cells KATP channel openers belonging to 3-alkylamino-7-halo-4H-1,2,4-benzothiadiazine 1,1-dioxides. J. Med. Chem. 2003, 46, 3342-3353.
de Tullio, P.; Pirotte, B.; Lebrun, P.; Fontaine, J.; Dupont, L.; Antoine, M.-H.; Ouedraogo, R.; Khelili, S.; Maggetto, C.; Masereel, B.; Diouf, O.; Podona, T.; Delarge, J. 3- and 4-substituted 4H-pyrido[4,3-e]-1,2,4- thiadiazine 1,1-dioxides as potassium channel openers: synthesis, pharmacological evaluation, and structure-activity relationships. J. Med. Chem. 1996, 39, 937-948.
Antoine, M.-H.; Gall, D.; Schiffmann, S. N.; Lebrun, P. Tricyclic antidepressant imipramine reduces the insulin secretory rate in islet cells of Wistar albino rats through a calcium antagonistic action. Diabetologia 2004, 47, 909-916.
Hamill, O. P.; Marty, A.; Neher, E.; Sakmann, B.; Sigworth, F. J. Improved patch-clamp techniques for high resolution current recording from cells and cell-free membrane patches. Pflügers Arch. 1981, 391, 85-100.
