3-Alkylamino-4H-pyrido[2,3-e]-1,2,4-thiadiazine 1,1-dioxides structurally related to diazoxide and pinacidil as potassium channel openers acting on vascular smooth muscle cells: design, synthesis and pharmacological evaluation
Pirotte, Bernard; Ouedraogo, R.; De Tullio, Pascalet al.
2000 • In Journal of Medicinal Chemistry, 43, p. 1456-1466
Pirotte, Bernard ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Ouedraogo, R.
De Tullio, Pascal ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Khelili, S.
Somers, F.
Boverie, S.
Dupont, L.
Fontaine, J.
Damas, J.
Lebrun, P.
Language :
English
Title :
3-Alkylamino-4H-pyrido[2,3-e]-1,2,4-thiadiazine 1,1-dioxides structurally related to diazoxide and pinacidil as potassium channel openers acting on vascular smooth muscle cells: design, synthesis and pharmacological evaluation
Publication date :
2000
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.
Standen, N. B.; Quayle, J. M.; Davies, N. W.; Brayden, J. E.; Huang, Y.; Nelson, M. T. Hyper-polarizing Vasodilators Activate ATP-Sensitive K+ Channels in Arterial Smooth Muscle. Science 1989, 245, 177-180.
Quayle, J. M.; Nelson, M. T.; Standen, N. B. ATP-Sensitive and Inwardly Rectifying Potassium Channels in Smooth Muscle. Physiol. Rev. 1997, 77, 1165-1232.
Pirotte, B.; de Tullio, P.; Lebrun, P.; Antoine, M.-H.; Fontaine, J.; Masereel, B.; Schynts, M.; Dupont, L.; Herchuelz, A.; Delarge, J. 3-(Alkylamino)-4H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-Dioxides as powerful Inhibitors of Insulin Release from Rat Pancreatic B-Cells: a New Class of Potassium Channel Openers? J. Med. Chem. 1993, 36, 3211-3213.
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.
Pirotte, B.; Antoine, M.-H.; de Tullio, P.; Hermann, M.; Herchuelz, A.; Delarge, J.; Lebrun, P. A Pyridothiadiazine (BPDZ 44) as a New and Potent Activator of ATP-Sensitive K+ Channels. Biochem. Pharmacol. 1994, 47, 1381-1386.
Antoine, M.-H.; Pirotte, B.; Hermann, M.; de Tullio, P.; Delarge, J.; Herchuelz, A.; Lebrun, P. Cationic and Secretory Effects of BPDZ 44 and Diazoxide in Rat Pancreatic Islets. Experientia 1994, 50, 830-832.
Lebrun, P.; Antoine, M.-H.; Ouedraogo, R.; Dunne, M.; Kane, C.; Hermannn M.; Herchuelz, A.; Masereel, B.; J. Delarge, J.; de Tullio, P.; Pirotte, B. Activation of ATP-Dependent K+ Channels and Inhibition of Insulin Release: Effect of BPDZ 62. J. Pharmacol. Exp. Ther. 1996, 277, 156-162.
Pirotte, B.; de Tullio, P.; Lebrun, P. Recent Advances in Drugs Acting as Tissue Selective Potassium Channel Openers. Potassium Channel Modulators: ID Res. Alert 1996, 1, 1-4.
Khelili, S.; de Tullio, P.; Lebrun, P.; Fillet, M.; Antoine, M.-H.; Ouedraogo, R.; Dupont, L.; Fontaine, J.; Felekidis, A.; Leclerc, G.; Delarge, J.; Pirotte, B. Preparation and Pharmacological Evaluation of the R- and S-Enantiomers of 3-(2′-Butylamino)-4H- and 3-(3′-Methyl-2′-butylamino)-4H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-Dioxide, Two Tissue Selective ATP-Sensitive Potassium Channel Openers. Bioorg. Med. Chem. 1999, 7, 1513-1520.
de Tullio, P.; Pirotte, B.; Somers, F.; Boverie, S.; Lacan F.; Delarge, J. Study of the Ring Closure Reaction of o-Aminoaryl-sulfonamides with 1,1′-Thiocarbonyldiimidazole. Tetrahedron 1998, 54, 4935-4942.
Petersen, H. J.; Nielsen, C. K.; Arrigoni-Martelli, E. Synthesis and Hypotensive Activity of N-Alkyl-N″-cyano-N′-pyridylguanidines. J. Med. Chem. 1978, 21, 773-781.
Robertson, D. W.; Steinberg, M. I. Potassium Channel Modulators: Scientific Applications and Therapeutic Promise. J. Med. Chem. 1990, 33, 1529-1541.
Steinberg, M. I.; Wiest, S. A.; Zimmerman, K. M.; Ertel, P. J.; Kerry, G. B.; Robertson, D. W. Chiral Recognition of Pinacidil and Its 3-Pyridyl Isomer by Canine Cardiac and Smooth Muscle: Antagonism by Sulfonylureas. J. Pharmacol. Exp. Ther. 1991, 256, 222-229.
Manley, P. W.; Quast, U. Structure-activity Studies of Potassium Channel Opening in Pinacidil-type Cyanoguanidines, Nitroethenediamines, Thioureas, and Ureas. J. Med. Chem. 1992, 35, 2327-2340.
Davies, M. P.; McCurrie, J. R.; Wood, D. Comparative Effects of K+ Channel Modulating Agents on Contractions of Rat Intestinal Smooth Muscle. Eur. J. Pharmacol 1996, 297, 249-256.
Sun, Y. D.; Benishin, C. G. K+ Channel Openers Relax Longitudinal Muscle of Guinea Pig Ileum. Eur. J. Pharmacol. 1994, 271, 453-459.
de Tullio, P.; Pirotte, B.; Dupont, L.; Masereel, B.; Laeckmann, D.; Podona, T.; Diouf, O.; Lebrun, P.; Delarge, J. Synthesis and Structural Studies of a New Class of Heterocyclic Compounds: 1,2,4-Pyridothiadiazine 1,1-Dioxides, Pyridyl Analogues of 1,2,4-Benzothiadiazine 1,1-Dioxides. Tetrahedron 1995, 51, 3221-3234.
Hollingsworth, M.; Amedee, T.; Edwards, D.; Mironneau, J.; Savineau, J. P.; Small, R. C.; Weston, A. H. The Relaxant Action of BRL 34915 in Rat Uterus. Br. J. Pharmacol. 1987, 91, 803-813.
Piper, I.; Minshall, E.; Downing, S. J.; Hollingsworth, M.; Sandraei, H. Effects of Several Potassium Channel Openers and Glibenclamide on the Uterus of the Rat. Br. J. Pharmacol. 1990, 101, 901-907.
Antoine, M.-H.; Berkenboom, G.; Fang, Z.-Y.; Fontaine, J.; Herchuelz, A.; Lebrun, P. Mechanical and Ionic Response of Rat Aorta to Diazoxide. Eur. J. Pharmacol. 1992, 216, 299-306.
Lebrun, P.; Fang, Z. Y.; Antoine, M.-H.; Herchuelz, A.; Hermann, M.; Berkenboom, G.; Fontaine, J. Hypoglycemic Sulfonylureas Antagonize the Effects of Cromakalim and Pinacidil on 86Rb Fluxes and Contractile Activity in the Rat Aorta. Pharmacology 1990, 41, 36-48.
Pirotte, B.; Dupont, L.; de Tullio, P.; Masereel, B.; Schynts, M.; Delarge, J. Structural Study of Pinacidil, a Potassium Channel Opener Belonging to the Chemical Class of N-alkyl-N″-cyano-N′-pyridylguanidines. Helv. Chim. Acta 1993, 76, 1311-1318.
Aguilar-Bryan, L.; Clement, J. P.; Gonzalez, G.; Kunjilwar, K.; Babenko, A.; Bryan, J. Towards Understanding the Assembly and Structure of KATP Channels. Physiol. Rev. 1998, 78, 227-245.
Albert, A.; Serjeant, E. P. Determination of Ionization Constants; Chapman & Hall: London, 1971.
Sheldrick, G. M. SHELXS-97, a Program for the Solution of Crystal Structures; University of Gottingen: Göttingen, Germany, 1997.
Sheldrick, G. M. SHELXL-97, a Program for the Refinement of Crystal Structures from Diffraction Data; University of Göttingen: Göttingen, Germany, 1997.
International Tables for X-ray Crystallography; Reidel Publishing Co.: Dordrecht, The Netherlands, 1992; Vol. C, Tables 4.2.6.8 and 6.1.1.4.
Burnett, M. N.; Johnson, C. K. ORTEP-III, Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations; Report ORNL-6895. Oak Ridge National Laboratory: Oak Ridge, TN, 1996.
Leclercq-Meyer, V.; Marchand, J.; Woussen-Colle, M. C.; Giroix, M.-H.; Malaisse, W. J. Multiple Effects of Leucine on Glucagon, Insulin, and Somatostatin Secretion from the Perfused Rat Pancreas. Endocrinology 1985, 116, 1168-1174.
Paton, W. D. M. The Response of the Guinea-Pig Ileum to Electrical Stimulation by Coaxial Electrodes. J. Physiol. (London) 1955, 127, 40P-41P.