3- and 4-substituted 4H-pyrido[4,3-e]-1,2,4-thiadiazme 1,1-dioxides as potassium channel openers: Synthesis, pharmacological evaluation, and structure-activity relationships

Journal of Medicinal Chemistry

Volumn 39, Issue 4, 1996, Pages 937-948

  De Tullio, Pascal ^a   Pirotte, Bernard ^a   Lebrun, Philippe ^b   Fontaine, Jeanine ^b   Dupont, Léon ^a   Antoine, Marie Hélène ^b   Ouedraogo, Raogo ^b   Khelili, Smail ^a   Maggetto, Carine ^b   Masereel, Bernard ^a   Diouf, Ousmane ^a   Podona, Tchao ^a   Delarge, Jacques ^a  

^a UNIVERSITY OF LIÈGE   (Belgium)

^b UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

4H PYRIDO[4,3 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE DERIVATIVE; ADENOSINE TRIPHOSPHATE; DIAZOXIDE; INSULIN; POTASSIUM CHANNEL; POTASSIUM CHANNEL STIMULATING AGENT; THIADIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; AORTA; ARTICLE; DRUG BINDING SITE; DRUG SYNTHESIS; FEMALE; GUINEA PIG; ILEUM; INSULIN RELEASE; MALE; NONHUMAN; PANCREAS; PANCREAS ISLET BETA CELL; RAT; STRUCTURE ACTIVITY RELATION; VASCULAR SMOOTH MUSCLE;

ANIMALS; AORTA; DIAZOXIDE; FEMALE; GUINEA PIGS; ILEUM; INDICATORS AND REAGENTS; INSULIN; ISLETS OF LANGERHANS; MALE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; MUSCLE CONTRACTION; MUSCLE, SMOOTH; MUSCLE, SMOOTH, VASCULAR; MYOCARDIAL CONTRACTION; POTASSIUM CHANNELS; RATS; RATS, WISTAR; STRUCTURE-ACTIVITY RELATIONSHIP; THIADIAZINES; VASODILATOR AGENTS;

EID: 0030051553     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9500582     Document Type: Review

References (41)

1. Cook, N. S. The Pharmacology of Potassium Channels and their Therapeutic Potential. Trends Pharmacol. Sci. 1988, 9, 21-27.
2. Potassium Channels, Structure, Classification, Function and Therapeutic Potential; Cook, N. S., Ed.; Ellis Horwood Ltd.: Chichester, 1990.
3. Edwards, G.; Weston, A. H. The Pharmacology of ATP-Sensitive Potassium Channels. Annu. Rev. Pharmacol. Toxicol. 1993, 33, 597-637.
4. Lazdunski, M. ATP-Sensitive Potassium Channels: An Overview. J. Cardiovasc. Pharmacol. 1994, 24, S1-S5.
5. Ashcroft, F. M. Adenosine 5′-Triphosphate-sensitive Potassium Channels. Annu. Rev. Neurosci. 1988, 11, 97-118.
6. + Channels Plays a Crucial Role in the Control of Insulin Secretion. Pflügers Arch. 1989, 414, S115-120.
7. Kolb, H. A. Potassium Channels in Excitable and Non-Excitable Cells. Rev. Physiol. Biochem. Pharmacol. 1990, 15, 51-79.
8. Malaisse, W. J.; Lebrun, P. Mechanisms of Sulfonylurea-Induced Insulin Release. Diabetes Care 1990, 13, suppl 3, 9-17.
9. Robertson, D. W.; Steinberg, M. I. Potassium Channel Modulators. Scientific Applications and Therapeutic Promise. J. Med. Chem. 1990, 33, 1529-1541.
10. Longman, S. D.; Hamilton, T. C. Potassium Channel Activator Drugs: Mechanism of Action, Pharmacological Properties, and Therapeutic Potential. Med. Res. Rev. 1992, 12, 73-148.
11. Weston, A. H.; Edwards, G. Recent Progress in Potassium Channel Opener Pharmacology. Biochem. Pharmacol. 1992, 43, 47-54.
12. Lebrun, P.; Devreux, V.; Hermann, M.; Herchuelz, A. Similarities Between the Effects of Pinacidil and Diazoxide on Ionic and Secretory Events in Rat Pancreatic Islets. J. Pharmacol. Exp. Ther. 1989, 250, 1011-1018.
13. 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.
14. + Outflow from Pancreatic B-Cells. Eur. J. Pharmacol. 1988, 156, 283-286.
15. 86Rb Fluxes and Contractile Activity in the Rat Aorta. Pharmacology 1990, 41, 36-48.
16. 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.
17. + Channels. Biochem. Pharmacol. 1994, 47, 1381-1386.
18. 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.
19. Lebrun, P.; Antoine, M.-H.; Ouedraogo, R.; Herchuelz, A.; de Tullio, P.; Delarge, J.; Pirotte, B. Pyridothiadiazines as Potent Inhibitors of Glucose-Induced Insulin Release. Adv. Exp. Med. Biol. 1995, in press.
20. Delarge, J.; Lapière, C. Synthesis and properties of some substituted anilinopyridines. J. Pharm. Belg. 1973, 3, 283-290.
21. Lopez, N.; Basade, J.; Grant, A.; Krees, S.; Terry, M.; Viktora, J.; Wolff, F. AO44: an Improved Hyperglycemic Agent. Metab. Clin. Exp. 1971, 20, 373-383.
22. Girard, Y.; Atkinson, J. G.; Rokach, J. A New Synthesis of 1,2,4-Benzothiadiazines and a Selective Preparation of o-Aminobenzenesulphonamides. J. Chem. Soc., Perkin Trans. 1 1979, 1043-1047.
23. Topliss, J. G.; Yudis, M. D. Correlation of Antihypertensive Activity with Structure in a Series of 2H-1,2,4-Benzothiadiazine 1,1-dioxides Using the Substituent Constant Approach. J. Med. Chem. 1972, 15, 394-400.
24. 86Rb Outflow from Pancreatic Islets Cells. J. Pharmacol. Exp. Ther. 1990, 255, 948-953.
25. Wollweber, H.; Horstmann, H.; Stoepel, K.; Garthoff, B.; Puls, W.; Krause, H. P.; Thomas, G. 3-Amino-2H-benzothiadiazine-1,1-dioxide with Antihypertensive and Possibly Diabetogenic Activity. Arzneim.-Forsch. / Drug. Res. 1981, 31, 279-288.
26. 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.
27. Bandoli, G.; Nicolini, M. Crystal and Molecular structure of Diazoxide, an Antihypertensive Agent. J. Cryst. Mol. Struct. 1977, 7, 229-240.
28. Dupont, L.; Pirotte, B.; de Tullio, P.; Masereel, B.; Delarge, J. 3-Methyl-4H-pyrido[3,2-e][1,2,4]thiadiazine 1,1-dioxide. Actra Crystallogr. 1995, C51, 944-946.
29. Dupont, L.; de Tullio, P.; Pirotte; B.; Masereel, B.; Delarge, J. 3-Methyl-4H-pyrido[4,3-e][1,2,4]thiadiazine 1,1-dioxide Monohydrate. Actra Crystallogr. 1995, C51, 946-948.
30. 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.
31. ATP Openers. J. Cardiovasc. Pharmacol. 1994, 24, S12-S17.
32. Albert, A.; Serjeant, E. P. In Determination of Ionization Constants; Chapman & Hall, London, 1971.
33. Jonhson, C. K. ORTEP-II, a Fortran Thermal-Ellipsoid Plot Program for Crystal Structure Illustrations; Report ORNL-5318; Oak Ridge National Laboratory, TN, 1976.
34. Tripos Associates, Inc., 1699 S. Harley Rd., Suite 303, St. Louis, MO.
35. Stewart, J. J. P. MOPAC, a Semiempirical Molecular Orbital Program. J. Comput.-Aided Mol. Des. 1990, 4, 1-105.
36. Sheldrick, G. M. SHELXS 86, a Program for the Solution of Crystal Structures. University of Göttingen, Germany, 1986.
37. Sheldrick, G. M. SHELXL 93, a Program for the Refinement of Crystal Structures from Diffraction Data. University of Göttingen, Germany, 1993.
38. International Tables for X-Ray Crystallography; Hahn, Th., Ed.; Reidel Publishing Company: Dordrecht, The Netherlands, 1992; Vol. C, Tables 4.2.6.8 and 6.1.1.4.
39. Leclercq-Meyer, V.; Marchand, J.; Rebolledo, O.; Malaisse, W. J.; Leclercq, R. A. Combined Radioimmunoassay for Glucagon and Insulin. Diabetologia 1975, 11, 419-425.
40. Paton, W. D. M. The Response of the Guinea-Pig Ileum to Electrical Stimulation by Coaxial Electrodes. J. Physiol. (London) 1955, 127, 40P-41P.
41. Finet, M.; Godfraind, T.; Khoury, G. The Positive Inotropic Action of the Nifedipine Analog K 8644 in Guinea-Pig and Rat Isolated Cardiac Preparations. Br. J. Pharmacol. 1985, 86, 27-32.