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Volumn 46, Issue 17, 2003, Pages 3670-3679

Highly potent 1,4-benzothiazine derivatives as KATP-channel openers

Author keywords

[No Author keywords available]

Indexed keywords

2 (3,4 DIHYDRO 2,2 DIMETHYL 6 NITRO 2H 1,4 BENZOXAZIN 4 YL)PYRIDINE 1 OXIDE; 2,2 DIMETHYL 4 (1 OXO 2 CYCLOPENTEN 2 YL) 6 TRIFUOROMETHYL 3,4 DIHYDRO 2H 1,4 BENZOTHIAZINE; 2,2 DIMETHYL 6 NITRO 4 (1 OXO 2 CYCLOPENTEN 2 YL) 3,4 DIHYDRO 2H 1,4 BENZOTHIAZINE; 6 CYANO 2,2 DIMETHYL 4 (1 OXO 2 CYCLOPENTEN 2 YL) 3,4 DIHYDRO 2H 1,4 BENZOTHIAZINE; BENZOPYRAN DERIVATIVE; BENZOTHIAZINE DERIVATIVE; CROMAKALIM; CYCLOPENTENONE; FORMAMIDE; GLIBENCLAMIDE; GUANIDINE DERIVATIVE; LEMAKALIM; NICORANDIL; PINACIDIL; POTASSIUM CHANNEL; UNCLASSIFIED DRUG;

EID: 0041731570     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030791q     Document Type: Article
Times cited : (60)

References (54)
  • 3
    • 0035942510 scopus 로고    scopus 로고
    • Recent developments in the biology and medicinal chemistry of potassium channel modulators: Update from a decade of progress
    • (a) 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, 24, 1627-1653.
    • (2001) J. Med. Chem. , vol.24 , pp. 1627-1653
    • Coghlan, M.J.1    Carroll, W.A.2    Gopalakrishnan, M.3
  • 4
    • 0036016272 scopus 로고    scopus 로고
    • + channels as therapeutic drug targets
    • + Channels as Therapeutic Drug Targets. Phamacol. Ther. 2002, 94, 157-182.
    • (2002) Phamacol. Ther. , vol.94 , pp. 157-182
    • Wickenden, A.D.1
  • 7
    • 0033529535 scopus 로고    scopus 로고
    • The molecular assembly of ATP-sensitive potassium channels. Determinants on the pore forming subunit
    • (b) Giblin, J. P.; Leaney, J. L.; Tinker, A. The Molecular Assembly of ATP-sensitive Potassium Channels. Determinants on the Pore Forming Subunit. J. Biol. Chem. 1999, 274, 22652-22659.
    • (1999) J. Biol. Chem. , vol.274 , pp. 22652-22659
    • Giblin, J.P.1    Leaney, J.L.2    Tinker, A.3
  • 8
    • 0033214491 scopus 로고    scopus 로고
    • Identification of the potassium channel opener site on sulfonylurea receptors
    • (a) Uhde, I.; Toman, A.; Gross, I.; Schwanstecher, C.; Schwanstecher, M. Identification of the Potassium Channel Opener Site on Sulfonylurea Receptors. J. Biol. Chem. 1999, 274, 28079-28082.
    • (1999) J. Biol. Chem. , vol.274 , pp. 28079-28082
    • Uhde, I.1    Toman, A.2    Gross, I.3    Schwanstecher, C.4    Schwanstecher, M.5
  • 11
    • 0022542171 scopus 로고
    • Comparison of the effects of BRL34915 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.
    • (1986) Br. J. Pharmacol. , vol.88 , pp. 103-111
    • Hamilton, T.C.1    Weir, S.W.2    Weston, A.H.3
  • 12
    • 0042390910 scopus 로고
    • An investigation into the mechanism of action of pinacidil in rat blood vessels
    • (a) 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 , pp. 126
    • Southerton, J.S.1    Taylor, S.G.2    Weir, S.W.3    Weston, A.H.4
  • 13
    • 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
    • (b) 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.
    • (1987) Br. J. Pharmacol. , vol.91 , pp. 421-429
    • Bray, K.M.1    Newgreen, D.T.2    Small, R.C.3    Southerton, J.S.4    Taylor, S.G.5    Weir, S.W.6    Weston, A.H.7
  • 14
    • 0018830671 scopus 로고
    • Effect of 2-nicotinamidoethyl nitrate on the membrane potential of the left atrial muscles 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-Schmiedebergs Arch. Pharmacol. 1980, 312, 69-76.
    • (1980) Naunyin-Schmiedebergs Arch. Pharmacol. , vol.312 , pp. 69-76
    • Yanagisawa, T.1    Taira, N.2
  • 15
    • 0037126931 scopus 로고    scopus 로고
    • Potential role of potassium channel openers in the treatment of asthma and chronic obstructive pulmonary diseases
    • Pelaia, G.; Gallelli, L.; Vatrella, A.; Grembiale, R. D.; Maselli, R.; De Sarro, G. B.; Marsico, S. A. Potential Role of Potassium Channel Openers in the Treatment of Asthma and Chronic Obstructive Pulmonary Diseases. Life Sci. 2002, 70, 977-990.
    • (2002) Life Sci. , vol.70 , pp. 977-990
    • Pelaia, G.1    Gallelli, L.2    Vatrella, A.3    Grembiale, R.D.4    Maselli, R.5    De Sarro, G.B.6    Marsico, S.A.7
  • 16
    • 0035184357 scopus 로고    scopus 로고
    • Pharmacolgical agents for the treatment of urinary incontinence due to overactive bladder
    • Wein, A. J. Pharmacolgical Agents for the Treatment of Urinary Incontinence Due to Overactive Bladder. Exp. Opin. Invest. Drugs 2001, 10, 65-83.
    • (2001) Exp. Opin. Invest. Drugs , vol.10 , pp. 65-83
    • Wein, A.J.1
  • 18
    • 0035675210 scopus 로고    scopus 로고
    • Minoxidil-induced hair growth is mediated by adenosine in cultured dermal papilla cells: Possible involvement of sulfonylurea receptor 2B as a target of minoxidil
    • (b) Li, M.; Marubayashi, A.; Nakaya, J.; Fukui, K.; Arase, S. Minoxidil-induced Hair Growth is mediated by Adenosine in Cultured Dermal Papilla Cells: Possible Involvement of Sulfonylurea Receptor 2B as a Target of Minoxidil. J. Invest. Dermatol. 2001, 117, 1594-1600.
    • (2001) J. Invest. Dermatol. , vol.117 , pp. 1594-1600
    • Li, M.1    Marubayashi, A.2    Nakaya, J.3    Fukui, K.4    Arase, S.5
  • 19
    • 0033837022 scopus 로고    scopus 로고
    • ATP-sensitive potassium channels: A review of their cardioprotective pharmacology
    • Grover, G. J.; Garlid, K. D. ATP-Sensitive Potassium Channels: a Review of Their Cardioprotective Pharmacology. J. Mol. Cell. Cardiol. 2000, 32, 677-695.
    • (2000) J. Mol. Cell. Cardiol. , vol.32 , pp. 677-695
    • Grover, G.J.1    Garlid, K.D.2
  • 20
    • 0034284804 scopus 로고    scopus 로고
    • Lipid metabolism as a target for potassium channel effectors
    • Szewczyk, A.; Pikula, S. Lipid Metabolism as a Target for Potassium Channel Effectors. Biochem. Pharmacol. 2000, 60, 607-614.
    • (2000) Biochem. Pharmacol. , vol.60 , pp. 607-614
    • Szewczyk, A.1    Pikula, S.2
  • 21
    • 0004890494 scopus 로고    scopus 로고
    • Structure-activity relationships of benzopyran based potassium channel activators
    • Evans, J. M., Hamilton, T. C., Longman S. D., Stemp, G., Eds.; 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
  • 22
    • 0023887324 scopus 로고
    • Synthesis of selectively trifluoromethylated pyridine derivatives as potential antihypertensives
    • (a) Lang, R. W.; Wenk, P. F. Synthesis of Selectively Trifluoromethylated Pyridine Derivatives as Potential Antihypertensives. Helv. Chim. Acta 1988, 71, 596-601.
    • (1988) Helv. Chim. Acta , vol.71 , pp. 596-601
    • Lang, R.W.1    Wenk, P.F.2
  • 23
    • 0025012188 scopus 로고
    • Variation in the aromatic ring of cromakalim: Antihypertensive activity of pyranopyridines, 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
  • 24
    • 0026494945 scopus 로고
    • Thiophene systems. 14. Synthesis and antihypertensive activity of novel 7-(cyclic amido)-6-hydroxythieno[3,2-b]pyrans and related compounds as new potassium channel activators
    • (a) Sanfilippo, P. J.; McNally, J. J.; Press, J. B.; Fitzpatrick, L. J.; Urbanski, M. J.; Katz, L. B.; Giardino, E.; Falotico, R.; Salata, J.; Moore, J. B.; Miller, W. Thiophene Systems. 14. Synthesis and Antihypertensive Activity of Novel 7-(Cyclic amido)-6-hydroxythieno[3,2-b]pyrans and Related Compounds as New Potassium Channel Activators. J. Med. Chem. 1992, 35, 4425-4435.
    • (1992) J. Med. Chem. , vol.35 , pp. 4425-4435
    • Sanfilippo, P.J.1    McNally, J.J.2    Press, J.B.3    Fitzpatrick, L.J.4    Urbanski, M.J.5    Katz, L.B.6    Giardino, E.7    Falotico, R.8    Salata, J.9    Moore, J.B.10    Miller, W.11
  • 26
    • 0027155104 scopus 로고
    • Thiophene systems. 15. Synthesis and antihypertensive activity of 7-(substituted benzamido)-6-hydroxythieno[3,2-b]-pyrans as new potassium channel activators
    • (c) Sanfilippo, P. J.; McNally, J. J.; Press, J. B.; Falotico, R.; Giardino, E.; Katz, L. B. Thiophene Systems. 15. Synthesis and Antihypertensive Activity of 7-(Substituted Benzamido)-6-hydroxythieno[3,2-b]-pyrans as new Potassium Channel Activators. Bioorg. Med. Chem. Lett. 1993, 3, 1385-1388.
    • (1993) Bioorg. Med. Chem. Lett. , vol.3 , pp. 1385-1388
    • Sanfilippo, P.J.1    McNally, J.J.2    Press, J.B.3    Falotico, R.4    Giardino, E.5    Katz, L.B.6
  • 27
    • 0026334595 scopus 로고
    • Synthesis and antihypertensive activity of pyran oxygen and amide nitrogen replacement analogues of the potassium channel activator cromakalim
    • Ashwood, V. A.; Cassidy, F.; Evans, J. M.; Gagliardi, S.; Stemp, G. Synthesis and Antihypertensive Activity of Pyran Oxygen and Amide Nitrogen Replacement Analogues of the Potassium Channel Activator Cromakalim. J. Med. Chem. 1991, 34, 3261-3267.
    • (1991) J. Med. Chem. , vol.34 , pp. 3261-3267
    • Ashwood, V.A.1    Cassidy, F.2    Evans, J.M.3    Gagliardi, S.4    Stemp, G.5
  • 31
    • 37049088249 scopus 로고
    • 4-Amido-3,4-dihydro-2H-1-benzothiopyran-3-ols and their sulphoxide and sulfphone derivatives-cromakalim analogues
    • Smith, D. G. 4-Amido-3,4-dihydro-2H-1-benzothiopyran-3-ols and Their Sulphoxide and Sulfphone Derivatives-Cromakalim Analogues. J. Chem. Soc., Perkin Trans. 1 1990, 3187-3191.
    • (1990) J. Chem. Soc., Perkin Trans. 1 , pp. 3187-3191
    • Smith, D.G.1
  • 35
    • 0032791093 scopus 로고    scopus 로고
    • Novel potassium channel activators. II. Synthesis and pharmacological evaluation of 3,4-dihydro-2H-1,4-benzoxazine derivatives: Modification of the aromatic part
    • (c) Matsumoto, Y.; Tsuzuki, R.; Matsuhisa, A.; Masuda, N.; Yamagiwa, Y.; Yanagisawa, I.; Shibanuma, T.; Nohira, H. Novel Potassium Channel Activators. II. Synthesis and Pharmacological Evaluation of 3,4-Dihydro-2H-1,4-benzoxazine Derivatives: Modification of the Aromatic Part. Chem. Pharm. Bull. 1999, 47, 971-979.
    • (1999) Chem. Pharm. Bull. , vol.47 , pp. 971-979
    • Matsumoto, Y.1    Tsuzuki, R.2    Matsuhisa, A.3    Masuda, N.4    Yamagiwa, Y.5    Yanagisawa, I.6    Shibanuma, T.7    Nohira, H.8
  • 36
    • 0034082766 scopus 로고    scopus 로고
    • Novel potassium channel activators. III. Synthesis and pharmacological evaluation of 3,4-dihydro-2H-1,4-benzoxazine Derivatives: Modification at the 2 position
    • (d) Matsumoto, Y.; Uchida, W.; Nakahara, H.; Yanagisawa, I.; Shibanuma, T.; Nohira, H. Novel Potassium Channel Activators. III. Synthesis and Pharmacological Evaluation of 3,4-Dihydro-2H-1,4-benzoxazine Derivatives: Modification at the 2 Position. Chem. Pharm. Bull. 2000, 48, 428-432.
    • (2000) Chem. Pharm. Bull. , vol.48 , pp. 428-432
    • Matsumoto, Y.1    Uchida, W.2    Nakahara, H.3    Yanagisawa, I.4    Shibanuma, T.5    Nohira, H.6
  • 41
    • 0033999086 scopus 로고    scopus 로고
    • Novel potassium channel openers. Part 4: Transformation of the 1,4-benzoxazine skeleton into 1,4-benzothiazine, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroquinoxaline, indoline, and 1,5-benzoxazepine
    • Matsumoto, Y.; Tsuzuki, R.; Matsuhisa, A.; Yoden, T.; Yamagiwa, Y.; Yanagisawa, I.; Shibanuma, T.; Nohira, H. Novel Potassium Channel Openers. Part 4: Transformation of the 1,4-Benzoxazine Skeleton into 1,4-Benzothiazine, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-Tetrahydroquinoxaline, Indoline, and 1,5-Benzoxazepine. Bioorg. Med. Chem. 2000, 8, 393-404.
    • (2000) Bioorg. Med. Chem. , vol.8 , pp. 393-404
    • Matsumoto, Y.1    Tsuzuki, R.2    Matsuhisa, A.3    Yoden, T.4    Yamagiwa, Y.5    Yanagisawa, I.6    Shibanuma, T.7    Nohira, H.8
  • 42
    • 0042390909 scopus 로고    scopus 로고
    • note
    • The 1,4-benzothiazine derivatives reported in ref 26 are 4-acetonyl-3,4-dihydro-2,2-dimethyl-6-nitro-2H-1,4-benzothiazine and its sulfoxide and sulfone analogues.
  • 45
    • 0025647830 scopus 로고
    • Enantiomers of 8-(3-tert-Butylamino-2-hydroxypropoxy)-3,4-dihydro-3-oxo-2H-(1,4)benzothiazine: Racemic resolution, chiral synthesis and biological activity
    • (c) Schiaffella, F.; Fringuelli, R.; Cecchetti, V.; Fravolini, A.; Angeli, P.; Marucci, G. Enantiomers of 8-(3-tert-Butylamino-2-hydroxypropoxy)-3,4-dihydro-3-oxo-2H-(1,4)benzothiazine: Racemic Resolution, Chiral Synthesis and Biological Activity. Il Farmaco 1990, 45, 1299-1307.
    • (1990) Il Farmaco , vol.45 , pp. 1299-1307
    • Schiaffella, F.1    Fringuelli, R.2    Cecchetti, V.3    Fravolini, A.4    Angeli, P.5    Marucci, G.6
  • 46
    • 0025768526 scopus 로고
    • Symbiotic approach to drug design: N-[(4-chloro-3-sulfamoylbenzamido)-ethyl]propanolamine derivatives as β-adrenergic blocking agents with diuretic activity
    • (d) Cecchetti, V.; Schiaffella, F.; Tabarrini, O.; Zhou, W.; Fravolini, A.; Goi, A.; Bruni, G.; Segre, G. Symbiotic Approach to Drug Design: N-[(4-Chloro-3-sulfamoylbenzamido)-ethyl]propanolamine Derivatives as β-Adrenergic Blocking Agents with Diuretic Activity. Eur. J. Med. Chem. 1991, 26, 381-386.
    • (1991) Eur. J. Med. Chem. , vol.26 , pp. 381-386
    • Cecchetti, V.1    Schiaffella, F.2    Tabarrini, O.3    Zhou, W.4    Fravolini, A.5    Goi, A.6    Bruni, G.7    Segre, G.8
  • 47
    • 0027393740 scopus 로고
    • o-chlorobenzenesulfonamidic derivatives of (Aryloxy)propanolamines as β-blocking/diuretic agents
    • (e) Cecchetti, V.; Fravolini, A.; Schiaffella, F.; Tabarrini, O.; Bruni, G.; Segre, G. o-Chlorobenzenesulfonamidic Derivatives of (Aryloxy) propanolamines as β-Blocking/Diuretic Agents. J. Med. Chem. 1993, 36, 157-161.
    • (1993) J. Med. Chem. , vol.36 , pp. 157-161
    • Cecchetti, V.1    Fravolini, A.2    Schiaffella, F.3    Tabarrini, O.4    Bruni, G.5    Segre, G.6
  • 48
    • 0034611135 scopus 로고    scopus 로고
    • (1,4-Benzothiazinyloxy)piperazine derivatives as potential antihypertensive agents
    • (f) Cecchetti, V.; Tabarrini, O.; Schaiaffella, F.; Fravolini, A. (1,4-Benzothiazinyloxy)piperazine Derivatives as Potential Antihypertensive Agents. Bioorg. Med. Chem. Lett. 2000, 10, 465-468.
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 465-468
    • Cecchetti, V.1    Tabarrini, O.2    Schaiaffella, F.3    Fravolini, A.4
  • 49
    • 0000974650 scopus 로고
    • Chemistry and synthesis of some dihydro-2H-1,4-benzothiazine derivatives
    • (a) Prasad, R. N.; Tietje, K. Chemistry and Synthesis of Some Dihydro-2H-1,4-benzothiazine Derivatives. Can. J. Chem. 1966, 44, 1247-1258.
    • (1966) Can. J. Chem. , vol.44 , pp. 1247-1258
    • Prasad, R.N.1    Tietje, K.2
  • 50
    • 0014489224 scopus 로고
    • Potential antihypertensive agents. III. 3,4-dihydro-2H-1,4-benzothiazine derivatives
    • (b) Prasad, R. N. Potential Antihypertensive Agents. III. 3,4-Dihydro-2H-1,4-benzothiazine Derivatives. J. Med. Chem. 1968, 12, 290-294.
    • (1968) J. Med. Chem. , vol.12 , pp. 290-294
    • Prasad, R.N.1
  • 51
    • 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. Fr. 1967, 2, 517-523.
    • (1967) Bull. Soc. Chim. Fr. , vol.2 , pp. 517-523
    • Solladié-Cavallo, A.1    Vièles, P.2
  • 52
  • 53
    • 0041889629 scopus 로고    scopus 로고
    • Conformational analysis of potassium channel activators
    • Evans, J. M., Hamilton, T. C., Longman S. D., Stemp, G., Eds; Taylor & Francis Ltd: London
    • Edge, C. M. Conformational Analysis of 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 79-97.
    • (1996) Potassium Channels and Their Modulators. From Synthesis to Clinical Experience , pp. 79-97
    • Edge, C.M.1


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