Effect on KATP channel activation properties and tissue selectivity of the nature of the substituent in the 7- and the 3-position of 4H-1,2,4-benzothiadiazine 1,1-dioxides

Journal of Medicinal Chemistry

Volumn 48, Issue 10, 2005, Pages 3492-3503

  Boverie, Stéphane ^a   Antoine, Marie Hélène ^b   Somers, Fabian ^a   Becker, Bénédicte ^b   Sebille, Sophie ^a   Ouedraogo, Raogo ^b   Counerotte, Stéphane ^a   Pirotte, Bernard ^a   Lebrun, Philippe ^b   De Tullio, Pascal ^a  

^a UNIVERSITY OF LIÈGE   (Belgium)

^b UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

3 (2' BUTYLAMINO) 7 METHOXY 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 (2' BUTYLAMINO) 7 TRIFLUOROMETHYL 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 (2'BUTYL)AMINO 7 METHYL 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 CYCLOBUTYLAMINO 7 METHOXY 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 CYCLOBUTYLAMINO 7 METHYL 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 ETHYLAMINO 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 ETHYLAMINO 7 METHYL 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 ETHYLAMINO 7 PENTYL 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 ISOPROPYLAMINO 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 ISOPROPYLAMINO 7 METHOXY 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 ISOPROPYLAMINO 7 METHYL 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 ISOPROPYLAMINO 7 PENTYL 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 ISOPROPYLAMINO 7 TRIFLUOROMETHYL 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 3 PROPYLAMINO 7 TRIFLUOROMETHYL 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 7 METHOXY 3 PROPYLAMINO 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; ADENOSINE TRIPHOSPHATE; BENZOTHIADIAZINE DERIVATIVE; POTASSIUM CHANNEL; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; AORTA CONSTRICTION; ARTICLE; CHANNEL GATING; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFECT; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; INSULIN RELEASE; MUSCLE RELAXATION; NONHUMAN; PANCREAS; PANCREAS ISLET BETA CELL; RAT; STRUCTURE ACTIVITY RELATION; VASCULAR RING; VASCULAR SMOOTH MUSCLE;

ADENOSINE TRIPHOSPHATE; ANIMALS; AORTA; BENZOTHIADIAZINES; INSULIN; ION CHANNEL GATING; ISLETS OF LANGERHANS; MUSCLE CONTRACTION; MUSCLE, SMOOTH, VASCULAR; POTASSIUM CHANNELS; RATS; RATS, WISTAR; STRUCTURE-ACTIVITY RELATIONSHIP; VASODILATOR AGENTS;

EID: 20844445619     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0311339     Document Type: Article

References (41)

1. Bryan, J.; Aguilar-Bryan, L. The ABCs of ATP-sensitive potassium channels: more pieces of the puzzle. Curr. Opin. Cell. Biol. 1997, 9, 553-559
2. Cook, N. S. The pharmacology of potassium channels and their therapeutic potential. Trends Pharmacol. Sci. 1988, 9, 21-28.
3. + channels in cardiac muscle. Nature 1983, 305, 147-148.
4. + channels in pancreatic B-cells, Nature 1984, 311, 271-273.
5. + channels in mammalian skeletal muscle cells. Eur. J. Pharmacol. 1993, 236, 419-426.
6. + channels in arterial smooth muscle. Science 1989, 245, 177-180.
7. 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.
8. + channel. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 9816-9820.
9. Lebrun, P.; Devreux, V.; Hermann, M.; Herchuelz, A. Pinacidil inhibits insulin release by increasing K+ outflow from pancreatic B-cells. Eur. J. Pharmacol. 1988, 156, 283-286.
10. 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.
11. Hamilton, T. C.; Weston, A. H. Cromakalim, nicorandil and pinacidil: novel drugs which open potassium channels in smooth muscle. Gen. Pharmacol. 1989, 20, 1-9.
12. + channels and inhibiting insulin release. Diabetologia 2000, 43, 723-732.
13. Cook, N. S.; Quast, U. Potassium channel pharmacology. In Potassium channels, structure, classification, function and therapeutic potential; Cook, N. S., Ed.; Ellis Horwood: Chichester U. K, 1990; pp 181-255.
14. Björk, E.; Berne, C.; Kämpe, O.; Wibell, P.; Oskarsson, F. A. Diazoxide treatment at onset preserves residual insulin secretion in adults with autoimmune diabetes. Diabetes 1996, 45, 1247-1430.
15. Alemzadeh, R.; Langley, G.; Upchurch, L.; Smith, P.; Slonim, A. E. Beneficial effect of diazoxide in obese hyperinsulinemic adults. J. Clin. Endocrinol. Metabol. 1998, 83, 1911-1915.
16. ATP channels. Annu. Rev. Physiol. 1998, 60, 667-687.
17. D'hahan, N.; Moreau, C.; Prost, A. L.; Jacquet, H.; Alekseev, A. E.; Terzic, A.; Vivaudou, M. Pharmacological plasticity of cardiac ATP-sensitive potassium channels toward diazoxide revealed by ADP. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 12162-12167.
18. Babenko, A. P.; Gonzalez, G.; Aguilar-Bryan, L.; Bryan, J. Reconstructed human cardiac K-ATP channels-functional identity with the native channels from the sarcolemma of human ventricular cells. Circ. Res. 1998, 83, 1132-1143.
19. + channel openers. Mol. Pharmacol. 1999, 56, 308-315.
20. ATP: an inward rectifier subunit plus the sulfonylurea receptor. Science 1995, 270, 1166-1170.
21. + channels. Neuron 1996, 16, 1011-1017.
22. + channel. J. Biol. Chem. 1996, 271, 24321-24324.
23. + channels. Biochem. Pharmacol. 1994, 47, 1381-1386
24. de Tullio, P.; Pirotte, B.; Lebrun, P.; Fontaine, J.; Dupont, L.; Antoine, M.-H.; Ouedraogo, R.; Khelili, S.; Magetto, 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.
25. Boverie, S.; Antoine, M.-H.; de Tullio, P.; Somers, F.; Becker, B.; Sebille, S.; Lebrun, P.; Pirotte, B. Effect on insulin release of compounds structurally related to the potassium channel opener 7-chloro-3-isopropylamino- 4H-1,2,4-benzothiadiazine 1,1-dioxide (BPDZ 73): introduction of heteroatoms on the 3-alkylamino side chain of the benzothiadiazine 1,1-dioxide ring. J. Pharm. Pharmacol. 2001, 53, 973-980.
26. ATP channel openers belonging to 3-alkylamino-7-halo-4H-1,2,4-benzothiadiazine 1,1-dioxides. J. Med. Chem. 2003, 46, 3342-3353.
27. Girard, Y.; Atkinson, J. G.; Rokach, J. A new synthesis of 1,2,4-benzothiadiazine and selective preparation of o-aminobenzene-sulfonamides. J. Chem. Soc., Perkin Trans. 1 1979, 1043-1047.
28. Di Bella, M.; Rinaldi, M.; Fabio, U.; Manicardi, G. Azione antimicrobica di derivati dell' 1,2,4-benzothiadiazine-1,1-diossido. Il Farmaco 1972, 27, 990-998.
29. 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.
30. Nielsen, F. E.; Bodvarsdottir, T. B.; Worsaae, A.; MacKay, P.; Stidsen, C. E.; Boonen, H. C., Pridal, L.; Arkhammar, P. O.; Wahl, P.; Ynddal, L.; Junager, F.; Dragsted, N.; Tagmose, T. M.; Mogensen, J. P.; Koch, A.; Treppendahl, S. P.; Hansen, J. B. 6-Chloro-3-alkylamino-4H-thieno[3, 2-e]-1,2,4-benzothiadiazine 1,1-dioxide derivatives potently and selectively activate ATP sensitive potassium channels of pancreatic B-cells. J. Med. Chem. 2002, 45, 4171-4187.
31. 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-4H-1,2,4-benzothiadiazine 1,1-dioxides on insulin-secreting cells. Pharm. Pharmacol. Commun. 2000, 6, 89-95.
32. Hansch, C.; Leo, A.; Unger, S. H.; Ki Hwan Kim; Nikaitani, D.; Lien, E. J. "Aromatic" substituent constants for structure - activity correlation. J. Med. Chem. 1973, 16, 1207-1216.
33. Manley, P. W.; Quast, U. Structure - activity studies of potassium channel opening in pinacidil-like cyanoguanidines, nitroethenediamines, thioureas, and ureas. J. Med. Chem. 1992, 35, 2327-2340.
34. 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.
35. Dabrowski, M.; Ashcroft, F. M.; Ashfield, R.; Lebrun, P.; Pirotte, B.; Egebjerg, J.; Hansen J. B.; Wahl, P. The novel diazoxide analogue 3-isopropylamino-7-methoxy-4H-1,2,4-benzothiadiazine 1,1-dioxide is a selective Kir6.2/SUR1 channel opener. Diabetes 2002, 51, 1896-1906.
36. Pitzer, K. K.; Werbovets, K. A.; Brendle, J. J.; Scovill, J. P. Synthesis and biological evaluation of 4-chloro-3,5-dinitrobenzotrifluoride analogues as antileishmanial agents. J. Med. Chem. 1998, 41, 4885-4889.
37. Jackman, G. B.; Petrow, V.; Stephenson, O.; Wild, A. M. Studies in the field of diuretic agents. Part VI: some sulphamoylbenzoic acids. J. Pharm. Pharmacol. 1962, 679-686.
38. Raffa, L.; Di Bella, M.; Melegari, M.; Vampa, G. Ricerce nel campo della 1,2,4-benzotiadiazina, Nota XXI - Derivati del 3-amino-1,2,4-benzotiadiazin-1,1- diossido. Il Farmaco 1862, XVII, 331-339.
39. ATP channel agonists. Bioorg. Med. Chem. Lett. 2002, 12, 2977-2980.
40. Albert, A.; Serjeant, E. P. The determination of ionization constants; Chapman & Hall: London, 1971; pp 44-64.
41. Leclerq-Meyer, V.; Marchand, J.; Woussen-Cole, M. C.; Giroix, M.-H.; Malaisse, W. J. Multiple effects of leucine on glucagons, insulin and somatostatin secretion from the perfused rat pancreas. Endocrinology 1985, 116, 1168-1174.