메뉴 건너뛰기




Volumn 40, Issue 1, 1997, Pages 24-34

Cardioselective antiischemic ATP-sensitive potassium channel (K(ATP)) openers. 5. Identification of 4-(N-aryl)-substituted benzopyran derivatives with high selectivity

Author keywords

[No Author keywords available]

Indexed keywords

4 [(4 CHLOROPHENYL) N (1H IMIDAZOL 2 YLMETHYL)AMINO] 3,4 DIHYDRO 3 HYDROXY 2,2 DIMETHYL 2H 1 BENZOPYRAN 6 CARBONITRILE; BENZOPYRAN DERIVATIVE; BMS 191095; CROMAKALIM; N (4 CHLOROPHENYL) N' CYANO N'' (6 CYANO 3,4 DIHYDRO 3 HYDROXY 2,2 DIMETHYL 2H 1 BENZOPYRAN 4 YL)GUANIDINE; POTASSIUM CHANNEL; UNCLASSIFIED DRUG;

EID: 8044260833     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9605905     Document Type: Article
Times cited : (75)

References (35)
  • 1
    • 0024460927 scopus 로고
    • Anti-Ischemic Effects of the Potassium Channel Activator Pinacidil and Cromakalim and the Reversal of these Effects with the Potassium Channel Blocker Glyburide
    • Grover, G. J.; McCullough, J. R.; Henry, D. E.; Conder, M. L.; Sleph, P. G. Anti-Ischemic Effects of the Potassium Channel Activator Pinacidil and Cromakalim and the Reversal of these Effects with the Potassium Channel Blocker Glyburide. J. Pharmacol. Exp. Ther. 1989, 251, 98-104.
    • (1989) J. Pharmacol. Exp. Ther. , vol.251 , pp. 98-104
    • Grover, G.J.1    McCullough, J.R.2    Henry, D.E.3    Conder, M.L.4    Sleph, P.G.5
  • 2
    • 0345718298 scopus 로고
    • Reduction of Ischemic Damage in Isolated Rat Hearts by the Potassium Channel Opener RP 52891
    • Grover, G. J.; Dzwonczyk, S.; Sleph, P. G. Reduction of Ischemic Damage in Isolated Rat Hearts by the Potassium Channel Opener RP 52891. Eur. J. Pharmacol. 1990, 69, 571-581.
    • (1990) Eur. J. Pharmacol. , vol.69 , pp. 571-581
    • Grover, G.J.1    Dzwonczyk, S.2    Sleph, P.G.3
  • 3
    • 0025696538 scopus 로고
    • Pharmacological Profile of Cromakalim in the treatment of Myocardial Ischemia in isolated rat Hearts and Anesthetized Dogs
    • Grover, G. J.; Sleph, P. G.; Dzwonczyk, S. Pharmacological Profile of Cromakalim in the treatment of Myocardial Ischemia in isolated rat Hearts and Anesthetized Dogs. J. Cardiovasc. Pharmacol. 1990, 16, 853-864.
    • (1990) J. Cardiovasc. Pharmacol. , vol.16 , pp. 853-864
    • Grover, G.J.1    Sleph, P.G.2    Dzwonczyk, S.3
  • 4
    • 0025358820 scopus 로고
    • The Protective Effects of Cromakalim and Pinacidil on Reperfusion Function and Infarct Size in Isolated Perfused Rat Hearts and Anesthetized Dogs
    • (a) Grover, G. J.; Dzwonczyk, S.; Parham, C. S.; Sleph, P. G. The Protective Effects of Cromakalim and Pinacidil on Reperfusion Function and Infarct Size in Isolated Perfused Rat Hearts and Anesthetized Dogs. Cardiovasc. Drugs Ther. 1990, 4, 465-474.
    • (1990) Cardiovasc. Drugs Ther. , vol.4 , pp. 465-474
    • Grover, G.J.1    Dzwonczyk, S.2    Parham, C.S.3    Sleph, P.G.4
  • 5
    • 85047679591 scopus 로고
    • Protective Effects of ATP Sensitive Potassium Channel Openers in Models of Myocardial Ischaemia
    • (b) Grover, G. J. Protective Effects of ATP Sensitive Potassium Channel Openers in Models of Myocardial Ischaemia. Cardiovasc. Res. 1994, 28, 778-782.
    • (1994) Cardiovasc. Res. , vol.28 , pp. 778-782
    • Grover, G.J.1
  • 6
    • 0025134235 scopus 로고
    • Profibrillatory Actions of Pinacidil in a Conscious Canine Model of Sudden Coronary Death
    • Chi, L.; Uprichard, A. C. G.; Lucchesi, B. R. Profibrillatory Actions of Pinacidil in a Conscious Canine Model of Sudden Coronary Death. J. Cardiovasc. Pharmacol. 1990, 15, 452-462.
    • (1990) J. Cardiovasc. Pharmacol. , vol.15 , pp. 452-462
    • Chi, L.1    Uprichard, A.C.G.2    Lucchesi, B.R.3
  • 7
    • 0028182641 scopus 로고
    • ATP Channels in Ischemic Preconditioning
    • ATP Channels in Ischemic Preconditioning. Cardiovasc. Res. 1994, 28, 783-787.
    • (1994) Cardiovasc. Res. , vol.28 , pp. 783-787
    • Parratt, J.R.1    Kane, K.A.2
  • 8
    • 0028098051 scopus 로고
    • Protection of the Heart by Ischemic Preconditioning: Mechanism and Possibilities for Pharmacological Exploitation
    • (b) Parratt, J. R. Protection of the Heart by Ischemic Preconditioning: Mechanism and Possibilities for Pharmacological Exploitation. Trends Pharmacol. Sci. 1994, 15, 19-25.
    • (1994) Trends Pharmacol. Sci. , vol.15 , pp. 19-25
    • Parratt, J.R.1
  • 9
    • 0026547286 scopus 로고
    • Blockade of ATP-Sensitive Potassium Channels Prevents Myocardial Preconditioning in Dogs
    • (a) Gross, G. J.; Auchampach, J. A. Blockade of ATP-Sensitive Potassium Channels Prevents Myocardial Preconditioning in Dogs. Circ. Res. 1990, 70, 223-233.
    • (1990) Circ. Res. , vol.70 , pp. 223-233
    • Gross, G.J.1    Auchampach, J.A.2
  • 10
    • 85047677669 scopus 로고
    • Blockade of Ischemic Preconditioning in Dogs by the Novel ATP-dependent Potassium Channel Antagonist Sodium 5-Hydroxydecanoate
    • (b) Auchampach, J. A.; Grover, G. J.; Gross, G. J. Blockade of Ischemic Preconditioning in Dogs by the Novel ATP-dependent Potassium Channel Antagonist Sodium 5-Hydroxydecanoate. Cardiovasc. Res. 1992, 26, 1054-1062.
    • (1992) Cardiovasc. Res. , vol.26 , pp. 1054-1062
    • Auchampach, J.A.1    Grover, G.J.2    Gross, G.J.3
  • 11
    • 0028152803 scopus 로고
    • The ATP-Dependent Potassium Channel: An Endogenous Cardioprotective mechanism
    • (c) Yao, Z.; Gross, G. J. The ATP-Dependent Potassium Channel: An Endogenous Cardioprotective mechanism. J. Cardiovasc. Pharmacol. 1994, 24, S28-S34.
    • (1994) J. Cardiovasc. Pharmacol. , vol.24
    • Yao, Z.1    Gross, G.J.2
  • 12
    • 3643052734 scopus 로고
    • Activation of KATP-Channels May Play a Role in the "Memory" of Ischemic Preconditioning (PC) in Anesthetized Dogs
    • (d) Yao, Z.; Mizumura, T.; Mei, D. A.; Gross, G. J. Activation of KATP-Channels May Play a Role in the "Memory" of Ischemic Preconditioning (PC) in Anesthetized Dogs. Circulation 1994, 90 (4 Part 2), I108.
    • (1994) Circulation , vol.90 , Issue.4 PART 2
    • Yao, Z.1    Mizumura, T.2    Mei, D.A.3    Gross, G.J.4
  • 13
    • 0027998778 scopus 로고
    • Ischemic Preconditioning during Coronary Artery Angioplasty is Prevented by Glybenclamide, a Selective ATP-Sensitive K+ channel Blocker
    • Tomai, F.; Crea, F.; Gaspardone, A.; Versaci, F.; De Paulis, R.; Pentadepeppo, A.; Chiariello, L.; Gioffre, P. Ischemic Preconditioning During Coronary Artery Angioplasty is Prevented by Glybenclamide, a Selective ATP-Sensitive K+ channel Blocker. Circulation 1994, 90, 700-705.
    • (1994) Circulation , vol.90 , pp. 700-705
    • Tomai, F.1    Crea, F.2    Gaspardone, A.3    Versaci, F.4    De Paulis, R.5    Pentadepeppo, A.6    Chiariello, L.7    Gioffre, P.8
  • 14
    • 0029070924 scopus 로고
    • K+ Channel Openers Prevent Global Ischemia-Induced Expression of c-fos, c-jun, Heat Shock Protein, and Amyloid β-Protein Precursor Genes and Neoronal Death in Rat Hippocampus
    • Heurteaux, C.; Lauritzen, I.; Widmann, C.; Lazdunski, M. K+ Channel Openers Prevent Global Ischemia-Induced Expression of c-fos, c-jun, Heat Shock Protein, and Amyloid β-Protein Precursor Genes and Neoronal Death in Rat Hippocampus. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 4666.
    • (1995) Proc. Natl. Acad. Sci. U.S.A. , vol.92 , pp. 4666
    • Heurteaux, C.1    Lauritzen, I.2    Widmann, C.3    Lazdunski, M.4
  • 16
    • 0028814519 scopus 로고
    • Cardioprotective Profile of the Cardiac-Selective ATP-Sensitive Potassium Channel Opener BMS-180448
    • Grover, G. J.; McCullough, J. R.; D'Alonzo, A. J.; Sargent, C. S.; Atwal, K. S. Cardioprotective Profile of the Cardiac-Selective ATP-Sensitive Potassium Channel Opener BMS-180448. J. Cardiovasc. Pharmacol. 1994, 25, 40-50.
    • (1994) J. Cardiovasc. Pharmacol. , vol.25 , pp. 40-50
    • Grover, G.J.1    McCullough, J.R.2    D'Alonzo, A.J.3    Sargent, C.S.4    Atwal, K.S.5
  • 18
    • 0025012188 scopus 로고
    • Variation in the Aromatic Ring of Cromakalim: Antihypertensive Activity of Pyranopyridines and 6-Alkyl-2H-1-benzopyrans
    • (b) 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-2H-1-benzopyrans. J. Med. Chem. 1990, 33, 3023-3027.
    • (1990) J. Med. Chem. , vol.33 , pp. 3023-3027
    • Burrell, G.1    Cassidy, F.2    Evans, J.M.3    Lightowler, D.4    Stemp, G.5
  • 20
    • 0025899165 scopus 로고
    • Enantiomerically Pure Epoxychromans via Asymmetric Catalysis
    • (d) For the synthesis of chiral epoxide 32, see: Lee, N. H.; Muci, A. R.; Jacobsen, E. R. Enantiomerically Pure Epoxychromans via Asymmetric Catalysis. Tetrahedron Lett. 1991, 32, 5055.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 5055
    • Lee, N.H.1    Muci, A.R.2    Jacobsen, E.R.3
  • 21
    • 0025277198 scopus 로고
    • Metal Salts as New Catalysts for Mild and Efficient Aminolysis of Oxiranes
    • Chini, M.; Crotti, P.; Macchia, F. Metal Salts as New Catalysts for Mild and Efficient Aminolysis of Oxiranes. Tetrahedron Lett. 1990, 31, 4661-4664.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 4661-4664
    • Chini, M.1    Crotti, P.2    Macchia, F.3
  • 22
    • 0025191236 scopus 로고
    • An Unusual Chemoselectivity in Cobalt (II) chloride catalyzed Cleavage of Oxiranes with Anilines: A Highly Regioselective Synthesis of β-Amino Alcohols
    • Iqbal, J.; Pandey, A. An Unusual Chemoselectivity in Cobalt (II) chloride catalyzed Cleavage of Oxiranes with Anilines: A Highly Regioselective Synthesis of β-Amino Alcohols. Tetrahedron Lett. 1990, 31, 575-576.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 575-576
    • Iqbal, J.1    Pandey, A.2
  • 23
    • 0030600147 scopus 로고    scopus 로고
    • Synthesis of 4-(N-Alkyl-N-heterocyclo)-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1- benzopyran-6-carbonitrile Derivatives via an Unusual 1,4-Oxygen to Nitrogen Migration
    • Ding, C. Z.; Miller, A. V. Synthesis of 4-(N-Alkyl-N-heterocyclo)-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1- benzopyran-6-carbonitrile Derivatives via an Unusual 1,4-Oxygen to Nitrogen Migration. Tetrahedron Lett. 1996, 37, 4447-4450.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 4447-4450
    • Ding, C.Z.1    Miller, A.V.2
  • 24
    • 0026095089 scopus 로고
    • Cardioprotective Effects of the Potassium Channel Opener Cromakalim: Stereoselectivity and Effects on Myocardial Adenine Nucleotides
    • Grover, G. J.; Newburger, J.; Sleph, P. G.; Dzwonczyk, S.; Taylor, S. C.; Ahmed, S. Z.; Atwal, K. S. Cardioprotective Effects of the Potassium Channel Opener Cromakalim: Stereoselectivity and Effects on Myocardial Adenine Nucleotides. J. Pharmacol. Exp. Ther. 1991, 257, 156-162.
    • (1991) J. Pharmacol. Exp. Ther. , vol.257 , pp. 156-162
    • Grover, G.J.1    Newburger, J.2    Sleph, P.G.3    Dzwonczyk, S.4    Taylor, S.C.5    Ahmed, S.Z.6    Atwal, K.S.7
  • 26
    • 0029003207 scopus 로고
    • Cardioselective anti-ischemic ATP-sensitive potassium channel openers 2. Structure-Activity Studies on Benzopyranyl Cyanoguanidines; Modification of the Benzopyran
    • Atwal, K. S.; Grover, G. J.; Ferrara, F. N.; Ahmed, S. Z.; Sleph, P. G.; Dzwonczyk, S.; Normandin, D. E. Cardioselective anti-ischemic ATP-sensitive potassium channel openers 2. Structure-Activity Studies on Benzopyranyl Cyanoguanidines; Modification of the Benzopyran. J. Med. Chem. 1995, 38, 1966-1973.
    • (1995) J. Med. Chem. , vol.38 , pp. 1966-1973
    • Atwal, K.S.1    Grover, G.J.2    Ferrara, F.N.3    Ahmed, S.Z.4    Sleph, P.G.5    Dzwonczyk, S.6    Normandin, D.E.7
  • 27
    • 0029166716 scopus 로고
    • Cardioselective anti-ischemic ATP-sensitive potassium channel openers 3. Structure-Activity Studies on Benzopyranyl Cyanoguanidines; Modification of the Cyanoguanidine Portion
    • Atwal, K. S.; Grover, G. J.; Ahmed, S. Z.; Sleph, P. G.; Dzwonczyk, S.; Baird, A. J.; Normandin, D. E. Cardioselective anti-ischemic ATP-sensitive potassium channel openers 3. Structure-Activity Studies on Benzopyranyl Cyanoguanidines; Modification of the Cyanoguanidine Portion. J. Med. Chem. 1995, 38, 3236.
    • (1995) J. Med. Chem. , vol.38 , pp. 3236
    • Atwal, K.S.1    Grover, G.J.2    Ahmed, S.Z.3    Sleph, P.G.4    Dzwonczyk, S.5    Baird, A.J.6    Normandin, D.E.7
  • 28
    • 8044250521 scopus 로고    scopus 로고
    • note
    • Compounds resulting from scission of other indole bonds had varying degrees of biological activity (unpublished results). Compounds 5 had the best profile in terms of cardioprotective potency and selectivity.
  • 29
    • 0025838238 scopus 로고
    • Effect of Potassium Channel Blockade on the Anti-Ischemic Actions of Mechanistically Diverse Agents
    • Sargent, C. A.; Smith, M. A.; Dzwonczyk, S.; Sleph, P. G.; Grover, G. J. Effect of Potassium Channel Blockade on the Anti-Ischemic Actions of Mechanistically Diverse Agents. J. Pharmacol. Exp. Ther. 1991, 259, 97-103.
    • (1991) J. Pharmacol. Exp. Ther. , vol.259 , pp. 97-103
    • Sargent, C.A.1    Smith, M.A.2    Dzwonczyk, S.3    Sleph, P.G.4    Grover, G.J.5
  • 31
    • 0029127039 scopus 로고
    • Regulation of Ion Channels by ABC Transporters that Secrete ATP
    • (b) Al-Awqati, Q. Regulation of Ion Channels by ABC Transporters that Secrete ATP. Science 1995, 269, 805.
    • (1995) Science , vol.269 , pp. 805
    • Al-Awqati, Q.1
  • 32
    • 0028789641 scopus 로고
    • + Channels: Paradigm Lost, Paradigm Regained
    • + Channels: Paradigm Lost, Paradigm Regained. Science 1995, 270, 1159.
    • (1995) Science , vol.270 , pp. 1159
    • Philipson, L.H.1
  • 33
    • 37049113396 scopus 로고
    • Formationb of 2,3-Dihydro-4(1H)-quinolones and Related Compounds via Frie-type Acid-catalyzed Rearrangement of 1-Arylazetidin-2-ones
    • Kano, S.; Ebata, T.; Shibuya, S. Formationb of 2,3-Dihydro-4(1H)-quinolones and Related Compounds via Frie-type Acid-catalyzed Rearrangement of 1-Arylazetidin-2-ones. J. Chem. Soc., Perkin Trans. 1 1980, 2105-2111.
    • (1980) J. Chem. Soc., Perkin Trans. 1 , pp. 2105-2111
    • Kano, S.1    Ebata, T.2    Shibuya, S.3
  • 34
    • 0027363856 scopus 로고
    • Regiospecific Synthesis of 3-Aminomethyl-5-substituted Isoxazoles: A Facile and Chemoselective Reduction of Azide to Amine by Sodium Borohydride Using 1,3-Propanedithiol as a Catalyst
    • Pei, Y.; Wickham, B. O. S. Regiospecific Synthesis of 3-Aminomethyl-5-substituted Isoxazoles: A Facile and Chemoselective Reduction of Azide to Amine by Sodium Borohydride Using 1,3-Propanedithiol as a Catalyst. Tetrahedron Lett. 1993, 34, 7509-7512.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7509-7512
    • Pei, Y.1    Wickham, B.O.S.2
  • 35
    • 0025259351 scopus 로고
    • A Facile Synthesis of N-Arylaminomethyl Phosphonate
    • Ha, H.; Nam, G.; Park, K. A Facile Synthesis of N-Arylaminomethyl Phosphonate. Tetrahedron Lett. 1990, 31, 1567-1568.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 1567-1568
    • Ha, H.1    Nam, G.2    Park, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.