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

Journal of Medicinal Chemistry

Volumn 56, Issue 8, 2013, Pages 3247-3256

  Pirotte, Bernard ^a   De Tullio, Pascal ^a   Florence, Xavier ^b   Goffin, Eric ^a   Somers, Fabian ^a   Boverie, Stéphane ^a   Lebrun, Philippe ^b  

^a UNIVERSITY OF LIÈGE   (Belgium)

^b UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

7 FLUORO 3 (1 PHENYLETHYL)SULFANYL 4H 1,2,4 BENZITHIADIAZINE 1,1 DIOXIDE MONOHYDRATE; ADENOSINE TRIPHOSPHATE SENSITIVE POTASSIUM CHANNEL; GLIBENCLAMIDE; MUSCLE RELAXANT AGENT; POTASSIUM CHANNEL STIMULATING AGENT; THIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ANIMAL CELL; ARTICLE; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; DISSOLUTION; DRUG ACTIVITY; DRUG CONFORMATION; DRUG STRUCTURE; HYDROGEN BOND; HYDROLYSIS; INSULIN RELEASE; MUSCLE RELAXATION; NONHUMAN; NUCLEOPHILICITY; PH; RAT; RECEPTOR BINDING; SMOOTH MUSCLE FIBER; STEREOSPECIFICITY; VASCULAR RING; VASCULAR SMOOTH MUSCLE;

ANIMALS; BENZOTHIADIAZINES; DIAZOXIDE; INSULIN-SECRETING CELLS; KATP CHANNELS; MUSCLE RELAXATION; MUSCLE, SMOOTH, VASCULAR; PARASYMPATHOLYTICS; STRUCTURE-ACTIVITY RELATIONSHIP; THIADIAZINES;

EID: 84876868688     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301743b     Document Type: Article

References (29)

1. ATP Channels Annu. Rev. Physiol. 1998, 60, 667-687
2. ATP: An Inward Rectifier Subunit Plus the Sulfonylurea Receptor Science 1995, 270, 1166-1170
3. + Channel Modulator Binding to Sulfonylurea Receptors SUR2A and SUR2B: Opposite Effects of MgADP Mol. Pharmacol. 1999, 55, 832-840
4. Seino, S. ATP-Sensitive Potassium Channels: A Model of Heteromultimeric Potassium Channel/Receptor Assemblies Annu. Rev. Physiol. 1999, 61, 337-362
5. 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
6. 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
7. 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
8. 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
9. 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
10. ATP Channel Activity J. Med. Chem. 2001, 44, 2575-2585
11. ATP Channel Openers Belonging to 3-Alkylamino-7-halo-4 H -1,2,4-benzothiadiazine 1,1-Dioxides J. Med. Chem. 2003, 46, 3342-3353
12. ATP 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
13. 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
14. ATP Channel Openers: Tissue Selectivity of Original 3-Alkylaminopyrido- and 3-Alkylaminobenzothiadiazine 1,1-Dioxides Biochem. Pharmacol. 2008, 75, 468-475
15. 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
16. 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
17. 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
18. 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
19. 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
20. 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
21. 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
22. 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
23. + Channels and Inhibiting Insulin Release Diabetologia 2000, 43, 723-732
24. 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
25. 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
26. 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
27. 3-Sulfamoylphenyl-5-dialkylaminoalkyl-1,2,4-oxadiazoles. GB 935523, Aug 28, 1963.
28. ATP Channel Openers: Modulation of the 4-Position Bioorg. Med. Chem. 2009, 17, 7723-7731
29. Albert, A.; Serjeant, E. P. The Determination of Ionization Constants; Chapman & Hall: London, 1971; pp 44-64.