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Volumn 49, Issue 14, 2006, Pages 4127-4139

New 3-alkylamino-4H-thieno-1,2,4-thiadiazine 1,1-dioxide derivatives activate ATP-sensitive potassium channels of pancreatic beta cells

Author keywords

[No Author keywords available]

Indexed keywords

6 CHLORO 3 (1 METHYL 1 PHENYLETHYL)AMINO 4H THIENO[3,2 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE; 6 CHLORO 3 (1 METHYLCYCLOPROPYL)AMINO 4H THIENO[3,2 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE; 6 CHLORO 3 (1 METHYLCYCLOPROPYL)AMINO 4H THIENO[3,2 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE DERIVATIVE; ADENOSINE TRIPHOSPHATE; AMINO 4H THIENO 1,2,4 THIADIAZINE 1,1 DIOXIDE DERIVATIVE; ANTIDIABETIC AGENT; INWARDLY RECTIFYING POTASSIUM CHANNEL SUBUNIT KIR6.2; NN 414; POTASSIUM CHANNEL; POTASSIUM CHANNEL STIMULATING AGENT; UNCLASSIFIED DRUG;

EID: 33745854821     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060042j     Document Type: Article
Times cited : (31)

References (45)
  • 1
    • 2942564708 scopus 로고    scopus 로고
    • + channels protect against a signal-transduction-linked and not freely reversible defect of insulin secretion in a rat islet transplantation model of type 2 diabetes
    • + Channels Protect Against a Signal-Transduction- Linked and Not Freely Reversible Defect of Insulin Secretion in a Rat Islet Transplantation Model of Type 2 Diabetes. Diabetologia 2004, 47, 885-891.
    • (2004) Diabetologia , vol.47 , pp. 885-891
    • Bjorklund, A.1    Hansen, J.B.2    Falkmer, S.3    Grill, V.4
  • 2
    • 0141866857 scopus 로고    scopus 로고
    • NN414, a SUR1/Kir6.2-selective potassium channel opener, reduces blood glucose and improves glucose tolerance in the VDF zucker rat
    • Carr, R. D.; Brand, C. L.; Bodvarsdottir, T. B.; Hansen, J. B.; Sturis, J. NN414, a SUR1/Kir6.2-Selective Potassium Channel Opener, Reduces Blood Glucose and Improves Glucose Tolerance in the VDF Zucker Rat. Diabetes 2003, 52, 2513-2518.
    • (2003) Diabetes , vol.52 , pp. 2513-2518
    • Carr, R.D.1    Brand, C.L.2    Bodvarsdottir, T.B.3    Hansen, J.B.4    Sturis, J.5
  • 4
    • 1442327747 scopus 로고    scopus 로고
    • Induction of beta-cell rest by a Kir6.2/SUR1-selective K(ATP)-channel opener preserves beta-cell insulin stores and insulin secretion in human islets cultured at high (11 mM) glucose
    • Ritzel, R. A.; Hansen, J. B.; Veldhuis, J. D.; Butler, P. C. Induction of Beta-Cell Rest by a Kir6.2/SUR1-Selective K(ATP)-Channel Opener Preserves Beta-Cell Insulin Stores and Insulin Secretion in Human Islets Cultured at High (11 mM) Glucose. J. Clin. Endocrinol. Metab. 2004, 89, 795-805.
    • (2004) J. Clin. Endocrinol. Metab. , vol.89 , pp. 795-805
    • Ritzel, R.A.1    Hansen, J.B.2    Veldhuis, J.D.3    Butler, P.C.4
  • 5
    • 2942560866 scopus 로고    scopus 로고
    • Inhibition of insulin secretion as a new drug target in the treatment of metabolic disorders
    • Hansen, J. B.; Arkhammar, P. O. G.; Bodvarsdottir, T. B.; Wahl, P. Inhibition of Insulin Secretion As a New Drug Target in the Treatment of Metabolic Disorders. Curr. Med. Chem. 2004, 11, 1595-1615.
    • (2004) Curr. Med. Chem. , vol.11 , pp. 1595-1615
    • Hansen, J.B.1    Arkhammar, P.O.G.2    Bodvarsdottir, T.B.3    Wahl, P.4
  • 6
    • 0842265545 scopus 로고    scopus 로고
    • Nine weeks of bedtime diazoxide is well tolerated and improves beta-cell function in subjects with type 2 diabetes
    • Qvigstad, E.; Kollind, M.; Grill, V. Nine Weeks of Bedtime Diazoxide Is Well Tolerated and Improves Beta-Cell Function in Subjects with Type 2 Diabetes. Diabetic Med. 2004, 21, 73-76.
    • (2004) Diabetic Med. , vol.21 , pp. 73-76
    • Qvigstad, E.1    Kollind, M.2    Grill, V.3
  • 7
    • 8544253979 scopus 로고    scopus 로고
    • Short-term intermittent exposure to diazoxide improves functional performance of beta-cells in a high-glucose environment
    • Yoshikawa, H.; Ma, Z. H.; Bjorklund, A.; Grill, V. Short-Term Intermittent Exposure to Diazoxide Improves Functional Performance of Beta-Cells in a High-Glucose Environment. Am. J. Physiol.: Endocrinol. Metab. 2004, 287, E1202-E1208.
    • (2004) Am. J. Physiol.: Endocrinol. Metab. , vol.287
    • Yoshikawa, H.1    Ma, Z.H.2    Bjorklund, A.3    Grill, V.4
  • 8
    • 0032788372 scopus 로고    scopus 로고
    • Molecular biology of adenosine triphosphate-sensitive potassium channels
    • Aguilar-Bryan, L.; Bryan, J. Molecular Biology of Adenosine Triphosphate-Sensitive Potassium Channels. Endocr. Rev. 1999, 20, 101-135.
    • (1999) Endocr. Rev. , vol.20 , pp. 101-135
    • Aguilar-Bryan, L.1    Bryan, J.2
  • 10
    • 0035942510 scopus 로고    scopus 로고
    • Recent developments in the biology and medicinal chemistry of potassium channel modulators: Update from a decade of progress
    • Coghlan, M. J.; Carroll, W. A.; Gopalakrishnan, M. Recent Developments in the Biology and Medicinal Chemistry of Potassium Channel Modulators: Update from a Decade of Progress. J. Med. Chem. 2001, 44, 1627-1653.
    • (2001) J. Med. Chem. , vol.44 , pp. 1627-1653
    • Coghlan, M.J.1    Carroll, W.A.2    Gopalakrishnan, M.3
  • 11
    • 33644866501 scopus 로고    scopus 로고
    • Towards selective Kir6.2/SUR1 potassium channel openers, medicinal chemistry and therapeutic perspectives
    • Hansen, J. B. Towards Selective Kir6.2/SUR1 Potassium Channel Openers, Medicinal Chemistry and Therapeutic Perspectives. Curr. Med. Chem. 2006, 13, 361-376.
    • (2006) Curr. Med. Chem. , vol.13 , pp. 361-376
    • Hansen, J.B.1
  • 13
    • 0142029955 scopus 로고    scopus 로고
    • Potent and selective activation of the pancreatic beta-cell type K(ATP) channel by two novel diazoxide analogues
    • Dabrowski, M.; Larsen, T.; Ashcroft, F. M.; Bondo-Hansen, J.; Wahl, P. Potent and Selective Activation of the Pancreatic Beta-Cell Type K(ATP) Channel by Two Novel Diazoxide Analogues. Diabetologia 2003, 46, 1375-1382.
    • (2003) Diabetologia , vol.46 , pp. 1375-1382
    • Dabrowski, M.1    Larsen, T.2    Ashcroft, F.M.3    Bondo-Hansen, J.4    Wahl, P.5
  • 17
    • 0036260040 scopus 로고    scopus 로고
    • The novel diazoxide analogue 3-isopropylamino-7-methoxy-4H-1,2,4- benzothiadiazine 1,1-dioxide is a selective Kir6.2/SUR1 channel opener
    • Dabrowski, M.; Ashcroft, F. M.; Ashtield, 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.
    • (2002) Diabetes , vol.51 , pp. 1896-1906
    • Dabrowski, M.1    Ashcroft, F.M.2    Ashtield, R.3    Lebrun, P.4    Pirotte, B.5    Egebjerg, J.6    Hansen, J.B.7    Wahl, P.8
  • 19
    • 35848945419 scopus 로고
    • Phosphorus in organic synthesis-VII: Diphenyl phosphorazidate (DPPA). A new convenient reagent for a modified curtius reaction
    • Ninomiya, K.; Shioiri, T.; Yamada, S. Phosphorus in Organic Synthesis-VII: Diphenyl Phosphorazidate (DPPA). A New Convenient Reagent for a Modified Curtius Reaction. Tetrahedron 1974, 30, 2151-2157.
    • (1974) Tetrahedron , vol.30 , pp. 2151-2157
    • Ninomiya, K.1    Shioiri, T.2    Yamada, S.3
  • 20
    • 0033578610 scopus 로고    scopus 로고
    • Properly tuned first fluoride-catalyzed TGME-mediated amination process for chloroimidazoles: Inexpensive technology for antihistaminic norastemizole
    • Senanayake, C. H.; Hong, Y. P.; Xiang, T. J.; Wilkinson, H. S.; Bakale, R. P.; Jurgens, A. R.; Pippert, M. F.; Butler, H. T.; Wald, S. A. Properly Tuned First Fluoride-Catalyzed TGME-Mediated Amination Process for Chloroimidazoles: Inexpensive Technology for Antihistaminic Norastemizole. Tetrahedron Lett. 1999, 40, 6875-6879.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 6875-6879
    • Senanayake, C.H.1    Hong, Y.P.2    Xiang, T.J.3    Wilkinson, H.S.4    Bakale, R.P.5    Jurgens, A.R.6    Pippert, M.F.7    Butler, H.T.8    Wald, S.A.9
  • 21
    • 33751391460 scopus 로고
    • 1H-pyrazole-1-carboxamide hydrochloride, an attractive reagent for guanylation of amines and its application to peptide synthesis
    • Bernatowiez, M. S.; Wu, Y.; Matsueda, G. R. 1H-Pyrazole-1-carboxamide Hydrochloride, an Attractive Reagent for Guanylation of Amines and its Application to Peptide Synthesis. J. Org. Chem. 1992, 57, 2497-2502.
    • (1992) J. Org. Chem. , vol.57 , pp. 2497-2502
    • Bernatowiez, M.S.1    Wu, Y.2    Matsueda, G.R.3
  • 22
    • 33745825346 scopus 로고    scopus 로고
    • note
    • Detailed procedures and reaction conditions for the ring closure will be given as Supporting Information.
  • 23
    • 0027157811 scopus 로고
    • Structural study of pinacidil, a potassium-channel opener belonging to the chemical class of N-alkyl-n″-cyano-n′- Pyridylguanidines
    • 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.
    • (1993) Helv. Chim. Acta , vol.76 , pp. 1311-1318
    • Pirotte, B.1    Dupont, L.2    De Tullio, P.3    Masereel, B.4    Schynts, M.5    Delarge, J.6
  • 24
    • 0028936431 scopus 로고
    • 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
    • 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.
    • (1995) Tetrahedron , vol.51 , pp. 3221-3234
    • De Tullio, P.1    Pirotte, B.2    Dupont, L.3    Masereel, B.4    Laeckmann, D.5    Podona, T.6    Diouf, O.7    Lebrun, P.8    Delarge, J.9
  • 28
    • 0001129552 scopus 로고
    • Crystal and molecular structure of diazoxide, an antihypertensive agent
    • Bandoli, G.; Nicolini, M. Crystal and Molecular Structure of Diazoxide, an Antihypertensive Agent. J. Cryst. Mol. Struct. 1977, 7, 229-240.
    • (1977) J. Cryst. Mol. Struct. , vol.7 , pp. 229-240
    • Bandoli, G.1    Nicolini, M.2
  • 29
    • 0026628740 scopus 로고
    • Structure-activity studies of potassium channel opening in pinacidil- type cyanoguanidines, nitroethenediamines. Thioureas, and ureas
    • Manley, P. W.; Quast, U. Structure-Activity Studies of Potassium Channel Opening in Pinacidil- Type Cyanoguanidines, Nitroethenediamines. Thioureas, and Ureas. J. Med. Chem. 1992, 35, 2327-2340.
    • (1992) J. Med. Chem. , vol.35 , pp. 2327-2340
    • Manley, P.W.1    Quast, U.2
  • 31
    • 7044221547 scopus 로고    scopus 로고
    • Establishment and application of in vitro membrane potential assays in cell lines with endogenous or recombinant expression of ATP-sensitive potassium channels (Kir6.2/SUR1) using a fluorescent probe kit
    • Arkhammar, P.; Wahl, P.; Gerlach, B.; Fremming, T.; Hansen, J. B. Establishment and Application of in Vitro Membrane Potential Assays in Cell Lines With Endogenous or Recombinant Expression of ATP-Sensitive Potassium Channels (Kir6.2/SUR1) Using a Fluorescent Probe Kit. J. Biomol. Screening 2004, 9, 382-390.
    • (2004) J. Biomol. Screening , vol.9 , pp. 382-390
    • Arkhammar, P.1    Wahl, P.2    Gerlach, B.3    Fremming, T.4    Hansen, J.B.5
  • 33
    • 0029016027 scopus 로고
    • Inexpensive, active KF for nucleophilic aromatic displacement reactions
    • Smyth, T. P.; Carey, A.; Hodnett, B. K. Inexpensive, Active KF for Nucleophilic Aromatic Displacement Reactions. Tetrahedron 1995, 51, 6363-6376.
    • (1995) Tetrahedron , vol.51 , pp. 6363-6376
    • Smyth, T.P.1    Carey, A.2    Hodnett, B.K.3
  • 34
    • 0042839399 scopus 로고    scopus 로고
    • A direct synthesis of 1-aryl- and 1-alkenylcyclopropylamines from ary1 and alkenyl nitriles
    • Bertus, P.; Szymoniak, J. A Direct Synthesis of 1-Aryl- and 1-Alkenylcyclopropylamines from Ary1 and Alkenyl Nitriles. J. Org. Chem. 2003, 68, 7133-7136.
    • (2003) J. Org. Chem. , vol.68 , pp. 7133-7136
    • Bertus, P.1    Szymoniak, J.2
  • 35
    • 0019417089 scopus 로고
    • Cerebrovasodilatation through selective inhibition of the enzyme carbonic anhydrase. 3. 5-(Arylthio)-. 5-(arylsulfinyl)-, and 5-(arylsulfonyl)thiophene- 2-sulfonamides
    • Barnish, I. T.; Cross, P. E.; Dickinson, R. P.; Parry, M. J.; Randall, M. J. Cerebrovasodilatation Through Selective Inhibition of the Enzyme Carbonic Anhydrase. 3. 5-(Arylthio)-. 5-(Arylsulfinyl)-, and 5-(Arylsulfonyl)thiophene-2- sulfonamides. J. Med. Chem. 1981, 24, 959-964.
    • (1981) J. Med. Chem. , vol.24 , pp. 959-964
    • Barnish, I.T.1    Cross, P.E.2    Dickinson, R.P.3    Parry, M.J.4    Randall, M.J.5
  • 36
    • 84987368258 scopus 로고
    • Inverted reactivity of aryllithium derivatives V. On the syntheses of thiocyano-, phenylsulfinyl-, and phenoxy derivatives of thiophenes and furans
    • Gronowitz, S.; Holm, B. Inverted Reactivity of Aryllithium Derivatives V. On the Syntheses of Thiocyano-, Phenylsulfinyl-, and Phenoxy Derivatives of Thiophenes and Furans. J. Heterocycl. Chem. 1977, 14, 281-288.
    • (1977) J. Heterocycl. Chem. , vol.14 , pp. 281-288
    • Gronowitz, S.1    Holm, B.2
  • 40
    • 11344284526 scopus 로고
    • Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds
    • Allen, F.; Kennard, O.; Watson, D.; Brammer, L.; Open, A.; Taylor. R. Tables of Bond Lengths Determined by X-ray and Neutron Diffraction. Part 1. Bond Lengths in Organic Compounds. J. Chem. Soc., Perkin Trans. 2 1987, S1-S19.
    • (1987) J. Chem. Soc., Perkin Trans. 2
    • Allen, F.1    Kennard, O.2    Watson, D.3    Brammer, L.4    Open, A.5    Taylor, R.6
  • 43
    • 0034855113 scopus 로고    scopus 로고
    • Effect of repaglinide on cloned beta cell, cardiac and smooth muscle types of ATP-sensitive potassium channels
    • Dabrowski, M.; Wahl, P.; Holmes, W. E.; Ashcroft, F. M. Effect of Repaglinide on Cloned Beta Cell, Cardiac and Smooth Muscle Types of ATP-Sensitive Potassium Channels. Diabetologia 2001, 44, 747-756.
    • (2001) Diabetologia , vol.44 , pp. 747-756
    • Dabrowski, M.1    Wahl, P.2    Holmes, W.E.3    Ashcroft, F.M.4
  • 44
    • 0017702173 scopus 로고
    • Contractile properties of small arterial resistance vessels in spontaneously hypertensive and normotensive rats
    • Mulvany, M. J.; Halpern, W. Contractile Properties of Small Arterial Resistance Vessels in Spontaneously Hypertensive and Normotensive Rats. Circ. Res. 1977, 41, 19-26.
    • (1977) Circ. Res. , vol.41 , pp. 19-26
    • Mulvany, M.J.1    Halpern, W.2
  • 45
    • 9644255738 scopus 로고    scopus 로고
    • Synthesis and pharmacological evaluation of 4H-1,4-benzothiazine-2- carbonitrile 1.1-dioxide and N-(2-cyanomethylsulfonylphenyl)acylamide derivatives as potential activators of ATP sensitive potassium channels
    • Schou, S. C.; Hansen, H. C.; Tagmose, T. M.; Boonen, H. C. M.; Worsaae. A.; Drabowski, M.; Wahl, P.; Arkhammer, P. O. G.; Bodvarsdottir, T.; Antoine, M. H.; Lebrun, P.; Hansen, J. B. Synthesis and Pharmacological Evaluation of 4H-1,4-Benzothiazine-2-carbonitrile 1.1-Dioxide and N-(2- Cyanomethylsulfonylphenyl)acylamide Derivatives as Potential Activators of ATP Sensitive Potassium Channels. Bioorg. Med. Chem. 2005, 13, 141-155.
    • (2005) Bioorg. Med. Chem. , vol.13 , pp. 141-155
    • Schou, S.C.1    Hansen, H.C.2    Tagmose, T.M.3    Boonen, H.C.M.4    Worsaae, A.5    Drabowski, M.6    Wahl, P.7    Arkhammer, P.O.G.8    Bodvarsdottir, T.9    Antoine, M.H.10    Lebrun, P.11    Hansen, J.B.12


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