2-alkyl-3-alkylamino-2H-benzo- and pyridothiadiazine 1,1-dioxides: From K+ATP channel openers to Ca++ channel blockers?

Biological Chemistry

Volumn 383, Issue 11, 2002, Pages 1759-1768

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

^a UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

^b UNIVERSITY OF LIÈGE   (Belgium)

Author keywords

BPDZ 44; BPDZ 73; Inhibition of insulin release; Potassium channel openers; Vasorelaxant activity

Indexed keywords

1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE DERIVATIVE; 3 ISOBUTYLAMINO 4H PYRIDO[4,3 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE; 7 CHLORO 3 ISOPROPYLAMINO 4H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; BDPZ 44; BDPZ 73; CALCIUM CHANNEL BLOCKING AGENT; DIAZOXIDE; PINACIDIL; POTASSIUM CHANNEL STIMULATING AGENT; PYRIDINE DERIVATIVE; THIADIAZINE DERIVATIVE; UNCLASSIFIED DRUG; VASODILATOR AGENT; VERAPAMIL;

ALKYLATION; ANIMAL TISSUE; ARTICLE; CHEMICAL BOND; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; INSULIN RELEASE; NONHUMAN; PANCREAS ISLET; PANCREAS ISLET BETA CELL; PRIORITY JOURNAL; RAT; SUBSTITUTION REACTION; VASCULAR RING; VASCULAR SMOOTH MUSCLE; VASODILATATION;

ALKANES; ANIMALS; AORTA, THORACIC; ATP-BINDING CASSETTE TRANSPORTERS; CALCIUM CHANNEL BLOCKERS; DIAZOXIDE; INDICATORS AND REAGENTS; INSULIN; ISLETS OF LANGERHANS; MUSCLE CONTRACTION; MUSCLE, SMOOTH, VASCULAR; POTASSIUM CHANNELS; POTASSIUM CHANNELS, INWARDLY RECTIFYING; RATS; RATS, WISTAR; STRUCTURE-ACTIVITY RELATIONSHIP; THIADIAZINES;

ANIMALIA;

EID: 0036869615     PISSN: 14316730     EISSN: None     Source Type: Journal    
DOI: 10.1515/BC.2002.197     Document Type: Article

References (30)

1. + channels in mammalian skeletal muscle cells. Eur. J. Pharmacol. 236, 419-426.
2. + channels. Trends Neurosci. 21, 288-294.
3. + channel. Proc. Natl. Acad. Sci. USA 85, 9816-9820.
4. Björk, E., Berne, C., Käimpe, O., Wibell, P., Oskarsson, P. and Karlsson, F.A. (1996). Diazoxide treatment at onset preserves residual insulin secretion in adults with autoimmune diabetes. Diabetes 45, 1427-1430.
5. + channels in pancreatic B-cells. Nature 311, 271-273.
6. De Tullio, P., Pirotte, B., Dupont, L., Masereel, B., Laeckmann, D., Podona, T, Diouf, O., Lebrun, P. and Delarge, J. (1995). 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 51, 3221-3234.
7. 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. and Delarge, J. (1996). 3- and 4-subtituted 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. 39, 937-948.
8. De Tullio, P, Pirotte, B., Somers, F, Boverie, S., Lacan, F. and Delarge, J. (1998). Study of the ring closure reaction of o-aminosulfonamides with 1,1'-thiocarbonyldiimidazole. Tetrahedron 54, 4935-4942.
9. De Tullio, P., Ouedraogo, R., Dupont, L., Somers, F, Boverie, S., Dogné, J.-M., Delarge, J. and Pirotte, B. (1999). Synthesis and structural studies of 3-alkylamino-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxides: a new class of heterocyclic compounds with therapeutical promises. Tetrahedron 55, 5419-5432.
10. Di Bella, M., Rinaldi, M., Fabio, U. and Manicardi, G. (1973). Azione antimicrobica di derivati dell'1,2,4-benzothiadiazin-1,1-diossido. II Farmaco 28, 411-417.
11. Di Bella, M., Albasini, A., Monzani, A. and Rinaldi, M. (1974). Ricerche nel campo della 1,2,4-benzotiadiazina. II Farmaco 29, 424-433.
12. Dupont, L., Somers, F, Boverie, S., Pirotte, B., Tinant, B. and de Tullio, P. (2001). 7-Chloro-2-methyl-2-methylamino-2H-1,2,4-benzothiadiazine 1,1-dioxide. Acta Cryst. E57, 652-654.
13. Dupont, L., Pirotte B. and de Tullio, P. (1999). 7-lodo-3-isopropylamino-4H-1,2,4-benzothiadiazine 1,1-dioxide. Acta Cryst. C55, 1152-1154.
14. Edwards, G. and Weston, A.H. (1993). The pharmacology of ATP-sensitive potassium channels. Annu. Rev. Pharmacol. Toxicol. 33, 597-637.
15. Khelili, S., de Tullio, P., Lebrun; P., Fillet, M., Antoine, M.-H., Ouedraogo, R., Dupont, L., Felekidis, A., Leclerc, G., Delarge, J. and Pirotte, B. (1999). 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. 7, 1513-1520.
16. Kolb, H.A. (1990). Potassium channels in excitable and non-excitable cells. Rev. Physiol. Biochem. Pharmacol. 15, 51-79.
17. + channel openers and insulin release. Life Sci. 51, 795-806.
18. + channels and inhibition of insulin release: effect of BPDZ 62. J. Pharm. Exp. Ther. 277, 156-162.
19. + channels and inhibiting insulin release. Diabetologia 43, 723-732.
20. Longman, S.D. and Hamilton T.C. (1992). Potassium channel activator drugs: mechanism of action, pharmacological properties, and therapeutic potential. Med. Res. Rev. 12, 73-148.
21. + channels in cardiac muscle. Nature 305, 147-148.
22. Ouedraogo, R., Fontaine, J., Antoine, M.-H., Pirotte, B. and Lebrun, P. (2000). Effects of 3-alkylamino-7-chloro-4H-pyrido[2,3-e]-1,2,4-thiadiazine 1,1-dioxides on smooth muscle contraction. Pharm. Pharmacol. Commun. 6, 97-100.
23. Quayle, J.M., Nelson, M.T. and Standen, N.B. (1997). ATP-sensitive and inwardly rectifying potassium channels in smooth muscle. Physiol. Rev. 77, 1165-1232.
24. Pirotte, B., de Tullio, P., Lebrun, P., Antoine, M.-H., Fontaine, J., Masereel, B., Schynts, M.,Dupont, L., Herchuelz, A. and Delarge, J. (1993). 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. 36, 3211-3213.
25. + channels. Biochem. Pharmacol. 47, 1381-1386.
26. Pirotte, B., Ouedraogo, R., de Tullio, P., Khelili, S., Somers, F, Boverie, S., Dupont L., Fontaine, J., Damas, J. and Lebrun, P. (2000). 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. J. Med. Chem. 43, 1456-1466.
27. + channels? Trends Pharmacol. Sci. 14, 332-337.
28. Robertson, D.W. and Steinberg, M.I. (1990). Potassium channel modulators: scientific applications and therapeutic promise. J. Med. Chem. 33, 1529-1541.
29. Seino, S. (1999). ATP-sensitive potassium channels: a model of heteromultimeric potassium channel/receptor assemblies. Annu. Rev. Physiol. 61, 337-362.
30. ATP channel activity. J. Med. Chem. 44, 2575-2585.