1,4,2-Benzo/pyridodithiazine 1,1-Dioxides Structurally Related to the ATP-Sensitive Potassium Channel Openers 1,2,4-Benzo/pyridothiadiazine 1,1-Dioxides Exert a Myorelaxant Activity Linked to a Distinct Mechanism of Action
Pirotte, Bernard; De Tullio, Pascal; Florence, X.et al.
2013 • In Journal of Medicinal Chemistry, 56, p. 3247-3256
Pirotte, Bernard ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
De Tullio, Pascal ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Florence, X.
Goffin, Eric ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Somers, F.
Boverie, S.
Lebrun, P.
Language :
English
Title :
1,4,2-Benzo/pyridodithiazine 1,1-Dioxides Structurally Related to the ATP-Sensitive Potassium Channel Openers 1,2,4-Benzo/pyridothiadiazine 1,1-Dioxides Exert a Myorelaxant Activity Linked to a Distinct Mechanism of Action
Publication date :
2013
Journal title :
Journal of Medicinal Chemistry
ISSN :
0022-2623
eISSN :
1520-4804
Publisher :
American Chemical Society, Washington, United States - District of Columbia
Babenko, A. P.; Aguilar-Bryan, L.; Bryan, J. A View of SUR/KIR6.X K ATP Channels Annu. Rev. Physiol. 1998, 60, 667-687
Inagaki, N.; Gonoi, T.; Clement, J. P.; Namba, N.; Inazawa, J.; Gonzalez, G.; Aguilar-Bryan, L.; Seino, S.; Bryan, J. Reconstitution of IKATP: An Inward Rectifier Subunit Plus the Sulfonylurea Receptor Science 1995, 270, 1166-1170
Hambrock, A.; Löffler-Walz, C.; Kloor, D.; Delabar, U.; Horio, Y.; Kurachi, Y.; Quast, U. ATP-Sensitive K+ Channel Modulator Binding to Sulfonylurea Receptors SUR2A and SUR2B: Opposite Effects of MgADP Mol. Pharmacol. 1999, 55, 832-840
Seino, S. ATP-Sensitive Potassium Channels: A Model of Heteromultimeric Potassium Channel/Receptor Assemblies Annu. Rev. Physiol. 1999, 61, 337-362
Shi, N. Q.; Ye, B.; Makielski, J. C. Function and Distribution of the SUR Isoforms and Splice Variants J. Mol. Cell. Cardiol. 2005, 39, 51-60
de Tullio, P.; Lebrun, P.; Florence, X.; Antoine, M.-H.; Francotte, P.; Pirotte, B. Selective Pancreatic ATP-Sensitive Potassium Channel Openers for the Treatment of Glucose Homeostasis Disorders Drugs Future 2006, 31, 991-1001
Pirotte, B.; de Tullio, P.; Lebrun, P.; Antoine, M.-H.; Fontaine, J.; Masereel, B.; Schynts, M.; Dupont, L.; Herchuelz, A.; Delarge, J. 3-(Alkylamino)-4 H -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 4 H -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.; Ouedraogo, R.; de Tullio, P.; Khelili, S.; Somers, F.; Boverie, S.; Dupont, L.; Fontaine, J.; Damas, J.; Lebrun, P. 3-Alkylamino-4 H -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 J. Med. Chem. 2000, 43, 1456-1466
Somers, F.; Ouedraogo, R.; Antoine, M.-H.; de Tullio, P.; Becker, B.; Fontaine, J.; Damas, J.; Dupont, L.; Rigo, B.; Delarge, J.; Lebrun, P.; Pirotte, B. Original 2-Alkylamino-6-halogenoquinazolin-4(3 H)-ones and KATP Channel Activity J. Med. Chem. 2001, 44, 2575-2585
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. Toward Tissue-Selective Pancreatic B-Cells KATP Channel Openers Belonging to 3-Alkylamino-7-halo-4 H -1,2,4-benzothiadiazine 1,1-Dioxides J. Med. Chem. 2003, 46, 3342-3353
Boverie, S.; Antoine, M.-H.; Somers, F.; Becker, B.; Sebille, S.; Ouedraogo, R.; Counerotte, S.; Pirotte, B.; Lebrun, P.; de Tullio, P. Effect on KATP Channel Activation Properties and Tissue Selectivity of the Nature of the Substituent in the 7- and the 3-Position of 4 H -1,2,4-Benzothiadiazine 1,1-Dioxides J. Med. Chem. 2005, 48, 3492-3503
de Tullio, P.; Boverie, S.; Becker, B.; Antoine, M.-H.; Nguyen, Q.-A.; Francotte, P.; Counerotte, S.; Sebille, S.; Pirotte, B.; Lebrun, P. 3-Alkylamino-4 H -1,2,4-benzothiadiazine 1,1-Dioxides as ATP-sensitive Potassium Channel Openers: Effect of 6,7-Disubstitution on Potency and Tissue Selectivity J. Med. Chem. 2005, 48, 4990-5000
Lebrun, P.; Becker, B.; Morel, N.; Ghisdal, P.; Antoine, M.-H.; de Tullio, P.; Pirotte, B. KATP Channel Openers: Tissue Selectivity of Original 3-Alkylaminopyrido- and 3-Alkylaminobenzothiadiazine 1,1-Dioxides Biochem. Pharmacol. 2008, 75, 468-475
Pirotte, B.; de Tullio, P.; Nguyen, Q.-A.; Somers, F.; Fraikin, P.; Florence, X.; Wahl, P.; Hansen, J. B.; Lebrun, P. Chloro-Substituted 3-Alkylamino-4 H -1,2,4-benzothiadiazine 1,1-Dioxides as ATP-Sensitive Potassium Channel Activators: Impact of the Position of the Chlorine Atom on the Aromatic Ring on Activity and Tissue Selectivity J. Med. Chem. 2010, 53, 147-154
Pirotte, B.; de Tullio, P.; Boverie, S.; Michaux, C.; Lebrun, P. Impact of the Nature of the Substituent at the 3-Position of 4 H -1,2,4- Benzothiadiazine 1,1-Dioxides on Their Opening Activity toward ATP-Sensitive Potassium Channels J. Med. Chem. 2011, 54, 3188-3199
de Tullio, P.; Servais, A.-C.; Fillet, M.; Gillotin, F.; Somers, F.; Chiap, P.; Lebrun, P.; Pirotte, B. Hydroxylated Analogues of ATP-Sensitive Potassium Channel Openers Belonging to the Group of 6- and/or 7-Substituted 3-Isopropylamino-4 H -1,2,4-benzothiadiazine 1,1-Dioxides: Toward an Improvement in Sulfonylurea Receptor 1 Selectivity and Metabolism Stability J. Med. Chem. 2011, 54, 8353-8361
Somers, F.; de Tullio, P.; Boverie, S.; Dogné, J.-M.; de Leval, X.; Antoine, M.-H.; Lebrun, P.; Pirotte, B. Synthesis and Biological Effects of New 3-Alkylamino-4 H -1,2,4-benzothiadiazine 1,1-Dioxides on Insulin-Secreting Cells Pharm. Pharmacol. Commun. 2000, 6, 89-95
Brzozowski, Z.; Sławiński, J.; Angielski, S.; Szczepańska-Konkiel, M. Derivatives of 1,1-Dioxo-1,4,2-benzodithiazine. III. Synthesis and Diuretic Properties of 3-(R,R1-Phenyl)amino-6-chloro-7- methyl-1,1-dioxo-1,4,2-benzodithiazines Acta Pol. Pharm. 1985, 42, 313-318
Brzozowski, Z.; Saîczewski, F.; Neamati, N. Synthesis and Anti-HIV-1 Activity of a Novel Series of 1,4,2-Benzodithiazine-dioxides Bioorg. Med. Chem. Lett. 2006, 16, 5298-5302
Brzozowski, Z.; Saîczewski, F.; Sławiński, J.; Bednarski, P. J.; Grünert, R.; Gdaniec, M. Synthesis, Structural Characterization, and in Vitro Antitumor Activity of Novel N -(6-Chloro-1,1-dioxo-1,4,2-benzodithiazin-3-yl)arylsulfonamides Bioorg. Med. Chem. 2007, 15, 2560-2572
Brzozowski, Z.; Saîczewski, F.; Slawiński, J. Syntheses of Potassium 1,1-Dioxopyrido[4,3- e ]-1,4,2-dithiazine-3-thiolate and Its Application to the Synthesis of Novel Sulfonamides with Potential Biological Activity J. Heterocycl. Chem. 2008, 45, 1407-1413
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
Ouedraogo, R.; Fontaine, J.; Antoine, M.-H.; Pirotte, B.; Lebrun, P. Effects of 3-Alkylamino-7-chloro-4 H -pyrido[2,3- e ]-1,2,4-thiadiazine 1,1-Dioxides on Smooth Muscle Contraction Pharm. Pharmacol. Commun. 2000, 6, 97-100
Becker, B.; Morel, N.; Vanbellinghen, A.-M.; Lebrun, P. Blockade of Calcium Entry in Smooth Muscle Cells by the Antidepressant Imipramine Biochem. Pharmacol. 2004, 68, 833-842
Dupont, L.; Somers, F.; de Tullio, P.; Pirotte, B. 3-Isopropylamino-7- nitro-1,4,2-benzodithiazine 1,1-Dioxide Acta Crystallogr. 2003, E59, o1509-o1511
3-Sulfamoylphenyl-5-dialkylaminoalkyl-1,2,4-oxadiazoles. GB 935523, Aug 28, 1963.
Florence, X.; Sebille, S.; de Tullio, P.; Lebrun, P.; Pirotte, B. New R / S -3,4-Dihydro-2,2-dimethyl-2 H -1-benzopyrans as KATP Channel Openers: Modulation of the 4-Position Bioorg. Med. Chem. 2009, 17, 7723-7731
Albert, A.; Serjeant, E. P. The Determination of Ionization Constants; Chapman & Hall: London, 1971; pp 44-64.