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Volumn 56, Issue 11, 2013, Pages 4718-4728

1,4-Benzothiazine ATP-sensitive potassium channel openers: Modifications at the C-2 and C-6 positions

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOTHIAZINE; ADENOSINE TRIPHOSPHATE SENSITIVE POTASSIUM CHANNEL; BENZOTHIAZINE DERIVATIVE; GLIBENCLAMIDE; HEXAMETHONIUM BROMIDE; INSULIN; LEMAKALIM; UNCLASSIFIED DRUG;

EID: 84879065994     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm400435a     Document Type: Article
Times cited : (20)

References (47)
  • 1
    • 33645322386 scopus 로고    scopus 로고
    • ATP channels as molecular sensors of cellular metabolism
    • ATP channels as molecular sensors of cellular metabolism Nature 2006, 440, 470-476
    • (2006) Nature , vol.440 , pp. 470-476
    • Nichols, C.G.1
  • 2
    • 0021086270 scopus 로고
    • + channels in cardiac muscle
    • + channels in cardiac muscle Nature 1983, 305, 147-148 (Pubitemid 14235671)
    • (1983) Nature , vol.305 , Issue.5930 , pp. 147-148
    • Noma, A.1
  • 5
    • 0029924673 scopus 로고    scopus 로고
    • Two types of ATP-sensitive potassium channels in rat portal vein smooth muscle cells
    • Zhang, H. L.; Bolton, T. B. Two types of ATP-sensitive potassium channels in rat portal vein smooth muscle cells Br. J. Pharmacol. 1996, 118, 105-114 (Pubitemid 26131253)
    • (1996) British Journal of Pharmacology , vol.118 , Issue.1 , pp. 105-114
    • Zhang, H.-L.1    Bolton, T.B.2
  • 6
    • 33645824084 scopus 로고    scopus 로고
    • + channels in smooth muscle
    • + channels in smooth muscle J. Physiol. 2006, 572, 617-624
    • (2006) J. Physiol. , vol.572 , pp. 617-624
    • Teramoto, N.1
  • 7
    • 0030772859 scopus 로고    scopus 로고
    • ATP-sensitive and inwardly rectifying potassium channels in smooth muscle
    • 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 (Pubitemid 27459582)
    • (1997) Physiological Reviews , vol.77 , Issue.4 , pp. 1165-1232
    • Quayle, J.M.1    Nelson, M.T.2    Standen, N.B.3
  • 9
    • 84870232189 scopus 로고    scopus 로고
    • ATP channel action in vascular tone regulation: From genetics to diseases
    • ATP channel action in vascular tone regulation: from genetics to diseases Acta Physiol. Sin. 2012, 64, 1-13
    • (2012) Acta Physiol. Sin. , vol.64 , pp. 1-13
    • Shi, W.W.1    Yang, Y.2    Shi, Y.3    Jiang, C.4
  • 12
    • 0022542171 scopus 로고
    • Comparison of the effects of BRL 34915 and verapamil on electrical and mechanical activity in rat portal vein
    • Hamilton, T. C.; Weir, S. W.; Weston, A. H. Comparison of the effects of BRL34915 and verapamil on electrical and mechanical activity in rat portal vein Br. J. Pharmacol. 1986, 88, 103-111 (Pubitemid 16020782)
    • (1986) British Journal of Pharmacology , vol.88 , Issue.1 , pp. 103-111
    • Hamilton, T.C.1    Weir, S.W.2    Weston, A.H.3
  • 13
    • 0042390910 scopus 로고
    • An investigation into the mechanism of action of pinacidil in rat blood vessels
    • Southerton, J. S.; Taylor, S. G.; Weir, S. W.; Weston, A. H. An investigation into the mechanism of action of pinacidil in rat blood vessels Br. J. Pharmacol. 1987, 90, 126P
    • (1987) Br. J. Pharmacol. , vol.90
    • Southerton, J.S.1    Taylor, S.G.2    Weir, S.W.3    Weston, A.H.4
  • 14
    • 0023227011 scopus 로고
    • Evidence that the mechanism of the inhibitory action of pinacidil in rat and guinea-pig smooth muscle differs from that of glyceryl trinitrate
    • Bray, K. M.; Newgreen, D. T.; Small, R. C.; Southerton, J. S.; Taylor, S. G.; Weir, S. W.; Weston, A. H. evidence that the mechanism of the inhibitory action of pinacidil in rat and guinea pig smooth muscle differs from that of glyceryl trinitrate Br. J. Pharmacol. 1987, 91, 421-429 (Pubitemid 17083989)
    • (1987) British Journal of Pharmacology , vol.91 , Issue.2 , pp. 421-429
    • Bray, K.M.1    Newgreen, D.T.2    Small, R.C.3
  • 15
    • 0018830671 scopus 로고
    • Effect of 2-nicotinamidethyl nitrate (SG-75) on the membrane potential of left atrial muscle fibres of the dog. Increase in potassium conductance
    • Yanagisawa, T.; Taira, N. Effect of 2-nicotinamidoethyl nitrate on the membrane potential of the left atrial muscles fibres of the dog. Increase in potassium conductance Naunyin-Schmiedeberg's Arch. Pharmacol. 1980, 312, 69-76 (Pubitemid 10120383)
    • (1980) Naunyn-Schmiedeberg's Archives of Pharmacology , vol.312 , Issue.1 , pp. 69-76
    • Yanagisawa, T.1    Taira, N.2
  • 18
    • 18144383488 scopus 로고    scopus 로고
    • Targeting small arteries of hypertensive status with novel ATP-sensitive potassium channel openers
    • DOI 10.2174/1570161053586895
    • Wang, H.; Zhang, Y. L.; Chen, Y. P. Targeting small arteries of hypertensive status with novel ATP-sensitive potassium channel openers Curr. Vasc. Pharmacol. 2005, 3, 119-124 (Pubitemid 40612985)
    • (2005) Current Vascular Pharmacology , vol.3 , Issue.2 , pp. 119-124
    • Wang, H.1    Zhang, Y.-L.2    Chen, Y.-P.3
  • 19
    • 0025980977 scopus 로고
    • Role of potassium channels in the vascular response to endogenous and pharmacological vasodilators
    • Brayden, J. E.; Quayle, J. M.; Standen, N. B.; Nelson, M. T. Role of potassium channels in the vascular response to endogenous and pharmacological vasodilators Blood Vessels 1991, 28, 147-153
    • (1991) Blood Vessels , vol.28 , pp. 147-153
    • Brayden, J.E.1    Quayle, J.M.2    Standen, N.B.3    Nelson, M.T.4
  • 20
    • 0026554833 scopus 로고
    • + channels regulate resting potential of pulmonary arterial smoth muscle cells
    • + channels regulate resting potential of pulmonary arterial smoth muscle cells Am. J. Physiol. 1992, 262, H916-H920
    • (1992) Am. J. Physiol. , vol.262
    • Clapp, L.H.1    Gurney, A.M.2
  • 22
    • 0026741427 scopus 로고
    • ATP-sensitive potassium channel is essential to maintain basal coronary vascular tone in vivo
    • Samaha, F. F.; Heineman, F. W.; Ince, C.; Fleming, J.; Balaban, R. S. ATP-sensitive potassium channel is essential to maintain basal coronary vascular tone in vivo Am. J. Physiol. 1992, 262, C1220-C1227
    • (1992) Am. J. Physiol. , vol.262
    • Samaha, F.F.1    Heineman, F.W.2    Ince, C.3    Fleming, J.4    Balaban, R.S.5
  • 23
    • 0027136582 scopus 로고
    • Arteriolar tone is determined by activity of ATP sensitive potassium channels
    • Jackson, W. F. Arteriolar tone is determined by activity of ATP sensitive potassium channels Am. J. Physiol. 1993, 265, H1797-H1803
    • (1993) Am. J. Physiol. , vol.265
    • Jackson, W.F.1
  • 24
    • 77957603729 scopus 로고    scopus 로고
    • Targeting hypertension with a new adenosine triphosphate-sensitive potassium channel opener iptakalim
    • Pan, Z.; Huang, J.; Cui, W.; Long, C.; Zhang, Y.; Wang, H. Targeting hypertension with a new adenosine triphosphate-sensitive potassium channel opener iptakalim J. Cardiovasc. Pharmacol. 2010, 56, 215-228
    • (2010) J. Cardiovasc. Pharmacol. , vol.56 , pp. 215-228
    • Pan, Z.1    Huang, J.2    Cui, W.3    Long, C.4    Zhang, Y.5    Wang, H.6
  • 26
    • 27144538657 scopus 로고    scopus 로고
    • Ibid. 2005, 48, 6766.
    • (2005) J. Med. Chem. , vol.48 , pp. 6766
  • 28
    • 0004890494 scopus 로고    scopus 로고
    • Structure-Activity Relationships of Benzopyran Based Potassium Channel Activators
    • In; Evans, J. M. Hamilton, T. C. Longman, S. D. Stemp, G. Taylor & Francis Ltd: London
    • Evans, J. M.; Stemp, G. Structure-Activity Relationships of Benzopyran Based Potassium Channel Activators. In Potassium Channels and Their Modulators. From Synthesis to Clinical Experience; Evans, J. M.; Hamilton, T. C.; Longman, S. D.; Stemp, G., Eds.; Taylor & Francis Ltd: London, 1996; pp 27-55.
    • (1996) Potassium Channels and Their Modulators. from Synthesis to Clinical Experience , pp. 27-55
    • Evans, J.M.1    Stemp, G.2
  • 29
    • 0033602529 scopus 로고    scopus 로고
    • 6-Substituted benzopyrans as potassium channel activators: Synthesis, vasodilator properties, and multivariate analysis
    • DOI 10.1021/jm981047m
    • Mannhold, R.; Cruciani, G.; Weber, H.; Lemoine, H.; Derix, A.; Weichel, C.; Clementi, M. 6-Substituted benzopyrans as potassium channel activators: synthesis, vasodilator properties, and multivariate analysis J. Med. Chem. 1999, 42, 981-991 (Pubitemid 29153427)
    • (1999) Journal of Medicinal Chemistry , vol.42 , Issue.6 , pp. 981-991
    • Mannhold, R.1    Cruciani, G.2    Weber, H.3    Lemoine, H.4    Derix, A.5    Weichel, C.6    Clementi, M.7
  • 30
    • 1242337465 scopus 로고    scopus 로고
    • ATP Channel Openers: Structure-Activity Relationships and Therapeutic Potential
    • DOI 10.1002/med.10060
    • ATP channel openers: structure-activity relationships and therapeutic potential Med. Res. Rev. 2004, 24, 213-266 (Pubitemid 38230680)
    • (2004) Medicinal Research Reviews , vol.24 , Issue.2 , pp. 213-266
    • Mannhold, R.1
  • 31
  • 33
    • 0023030013 scopus 로고
    • Synthesis and antihypertensive activity of 4-(cyclic amido)-2H-1- benzopyrans
    • DOI 10.1021/jm00161a011
    • Ashwood, V. A.; Buckingham, R. E.; Cassidy, F.; Evans, J. M.; Faruk, E. A.; Hamilton, T. C.; Nash, D. J.; Stemp, G.; Willcocks, K. Synthesis and antihypertensive activity of 4-(cyclic amido)-2 H -1-benzopyrans J. Med. Chem. 1986, 29, 2194-2201 (Pubitemid 17182293)
    • (1986) Journal of Medicinal Chemistry , vol.29 , Issue.11 , pp. 2194-2201
    • Ashwood, V.A.1    Buckingham, R.E.2    Cassidy, F.3
  • 36
    • 0025012188 scopus 로고
    • Variation in the aromatic ring of cromakalim: Antihypertensive activity of pyranopyridines and 6-alkyl-2H-1-benzopyrans
    • Burrell, G.; Cassidy, F.; Evans, J. M.; Lightowler, D.; Stemp, G. Variation in the aromatic ring of cromakalim: antihypertensive activity of pyranopyridines and 6-alkyl-2 H -1-benzopyrans J. Med. Chem. 1990, 33, 3023-3027 (Pubitemid 20349530)
    • (1990) Journal of Medicinal Chemistry , vol.33 , Issue.11 , pp. 3023-3027
    • Burrell, G.1    Cassidy, F.2    Evans, J.M.3    Lightowler, D.4    Stemp, G.5
  • 37
    • 0005201990 scopus 로고
    • Organic sulfur compounds. II. Catalyzed sodium borohydride reductions of selected α-(o -nitrophenylthio) acids
    • Coutts, R. T.; Barton, D. L.; Smith, E. M. Organic sulfur compounds. II. Catalyzed sodium borohydride reductions of selected α-(o -nitrophenylthio) acids Can. J. Chem. 1966, 44, 1733-1741
    • (1966) Can. J. Chem. , vol.44 , pp. 1733-1741
    • Coutts, R.T.1    Barton, D.L.2    Smith, E.M.3
  • 38
    • 0023130703 scopus 로고
    • Quinolonecarboxylic acids. 2. Synthesis and antibacterial evaluation of 7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzothiazine-6- carboxylic acids
    • DOI 10.1021/jm00386a005
    • Cecchetti, V.; Fravolini, A.; Fringuelli, R.; Mascellani, G.; Pagella, P.; Palmioli, M.; Segre, G.; Terni, P. Quinolonecarboxylic acids. 2. Synthesis and antibacterial evaluation of 7-oxo-2,3-dihydro-7 H -pyrido[1,2,3- de ][1,4]benzothiazine-6-carboxylic acids J. Med. Chem. 1987, 30, 465-473 (Pubitemid 17033650)
    • (1987) Journal of Medicinal Chemistry , vol.30 , Issue.3 , pp. 465-473
    • Cecchetti, V.1    Fravolini, A.2    Fringuelli, R.3
  • 39
    • 67650074166 scopus 로고    scopus 로고
    • Synthesis of 2-(arylamino)ethanethiols via Lewis acid catalyzed aminolysis of 2,2-dimethylthiirane as precursors of the 1,4-benzothiazine nucleus
    • Spogli, R.; Sabatini, S.; Manfroni, G.; Tabarrini, O.; Cecchetti, V. Synthesis of 2-(arylamino)ethanethiols via Lewis acid catalyzed aminolysis of 2,2-dimethylthiirane as precursors of the 1,4-benzothiazine nucleus Synthesis 2009, 9, 1513-1519
    • (2009) Synthesis , vol.9 , pp. 1513-1519
    • Spogli, R.1    Sabatini, S.2    Manfroni, G.3    Tabarrini, O.4    Cecchetti, V.5
  • 40
    • 85011188102 scopus 로고
    • Non-stereospecific ring expansion reactions of benzothiadiazoline sulphoxides
    • Shimizu, H.; Ueda, N.; Kataoka, T.; Hori, M. Non-stereospecific ring expansion reactions of benzothiadiazoline sulphoxides Chem. Pharm. Bull. 1984, 32, 2571-2590
    • (1984) Chem. Pharm. Bull. , vol.32 , pp. 2571-2590
    • Shimizu, H.1    Ueda, N.2    Kataoka, T.3    Hori, M.4
  • 41
    • 84879058018 scopus 로고
    • Nitro- and amino-3(4 H)-oxo-2 H -1,4-benzothiazines
    • Martani, A.; Fravolini, A.; Grandolini, G. Nitro- and amino-3(4 H)-oxo-2 H -1,4-benzothiazines Ann. Chim. (Rome) 1968, 58, 1226-1237
    • (1968) Ann. Chim. (Rome) , vol.58 , pp. 1226-1237
    • Martani, A.1    Fravolini, A.2    Grandolini, G.3
  • 42
    • 0026018623 scopus 로고
    • The design of a novel class of potassium channel activating drugs, 2-(2,2-dimethylbenzopyran-4yl)-pyridine-1-oxides
    • Attwood, M. R.; Jones, P. S.; Kay, P. B.; Paciorek, P. M.; Redshaw, S. The design of a novel class of potassium channel activating drugs, 2-(2,2-dimethylbenzopyran-4yl)-pyridine-1-oxides Life Sci. 1991, 48, 803-810
    • (1991) Life Sci. , vol.48 , pp. 803-810
    • Attwood, M.R.1    Jones, P.S.2    Kay, P.B.3    Paciorek, P.M.4    Redshaw, S.5
  • 44
    • 0035946507 scopus 로고    scopus 로고
    • Metabolic and functional studies on isolated islets in a new rat model of type 2 diabetes
    • DOI 10.1016/S0303-7207(01)00400-2, PII S0303720701004002
    • Novelli, M.; Fabregat, M. E.; Fernandez-Alvarez, J.; Gomis, R.; Masiello, P. Metabolic and functional studies on isolated islets in a new rat model of type 2 diabetes Mol. Cell. Endocrinol. 2001, 175, 57-66 (Pubitemid 32372543)
    • (2001) Molecular and Cellular Endocrinology , vol.175 , Issue.1-2 , pp. 57-66
    • Novelli, M.1    Fabregat, M.E.2    Fernandez-Alvarez, J.3    Gomis, R.4    Masiello, P.5
  • 45
    • 0024599316 scopus 로고
    • Control of insulin secretion by sulfonylureas, meglitidine and diazoxide in relation to their binding to the sulfonylurea receptor in pancreatic islets
    • DOI 10.1016/0006-2952(89)90327-4
    • Pantern, U.; Burgfeld, J.; Goerke, F.; Rennicke, M.; Schwanstecher, M.; Wallasch, A.; Zhkler, B. J.; Lenzen, S. Control of insulin secretion by sulfonylureas meglitinide and diazoxide in relation to their binding to the sulfonylurea receptor in pancreatic islets Biochem. Pharmacol. 1989, 38, 1217-1229 (Pubitemid 19101950)
    • (1989) Biochemical Pharmacology , vol.38 , Issue.8 , pp. 1217-1229
    • Panten, U.1    Burgfeld, J.2    Goerke, F.3    Rennicke, M.4    Schwanstecher, M.5    Wallasch, A.6    Zunkler, B.J.7    Lenzen, S.8
  • 46
    • 71749086139 scopus 로고    scopus 로고
    • New R / S -3,4-dihydro-2,2-dimethyl-2 H -1-benzopyrans as K(ATP) channel openers: Modulation of the 4-position
    • 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 K(ATP) channel openers: modulation of the 4-position Bioorg. Med. Chem. 2009, 17, 7723-7731
    • (2009) Bioorg. Med. Chem. , vol.17 , pp. 7723-7731
    • Florence, X.1    Sebille, S.2    De Tullio, P.3    Lebrun, P.4    Pirotte, B.5
  • 47
    • 0141735990 scopus 로고
    • Contribution à l′etude de quelques composés se rattachant aux séries oxy et thiodiacétique. i. Synthèse et spectres IR
    • Solladié-Cavallo, A.; Vièles, P. Contribution à l′etude de quelques composés se rattachant aux séries oxy et thiodiacétique. i. Synthèse et spectres IR Bull. Soc. Chim. France 1967, 2, 517-523
    • (1967) Bull. Soc. Chim. France , vol.2 , pp. 517
    • Solladié-Cavallo, A.1    Vièles, P.2


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