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Volumn 33, Issue 1, 2010, Pages 25-46

Synthesis of new 4,5-3(2H)pyridazinone derivatives and their cardiotonic, hypotensive, and platelet aggregation inhibition activities

Author keywords

4,5 dihydropyridazinones; Acute toxicity; Hypotensive; Pharmacophore models; Platelet aggregation inhibition; Positive inotropic (Cardiotonic)

Indexed keywords

4,5 DIHYDRO 3(2H)PYRADAZINONE DERIVATIVE; 6 (4 AMINOPHENYL) 4,5 DIHYDRO 3(2H) PYRIDAZINONE; 6 [4 [(3,5 DIMETHYL 1 (UN)SUBSTITUTED 4 PYRAZOLYLAZO)HYDRAZINO]PHENYL] 4,5 DIHYDRO 3(2H) PYRIDAZINONE DERIVATIVE; 6 [4 [2 (1 ACETYL 1 N N BUTYLCARBAMOYLMETHYLIDENE)HYDRAZINO]PHENYL] 4,5 DIHYDRO 3(2H) PYRIDAZINONE; 6 [4 [2 (3 AMINO 5 OXO PYRAZOLIN 4 YLIDENE)HYDRAZINO]PHENYL] 4,5 DIHYDRO 3(2H) PYRIDAZINONE; 6 [4 [2 (3 METHYL 5 OXO 1 (UN)SUBSTITUTED 4 PYRAZOLINYLIDENE)HYDRAZINO]PHENYL] 4,5 DIHYDRO 3(2H) PYRIDAZINONE DERIVATIVE; 6 [4 [2 (DISUBSTITUTED METHYLIDENE)HYDRAZINO]PHENYL] 4,5 DIHYDRO 3(2H) PYRIDAZINONE DERIVATIVE; 6 [4 [2 [1 ACETYL 1 (1 N IMINOETHYL)METHYLIDENE]HYDRAZINO]PHENYL] 4,5 DIHYDRO 3(2H) PYRIDAZINONE DERIVATIVE; 6 [4 [2 [1 N METHYLCARBAMOYL 1 [1 (N METHYLIMINO)ETHYL]METHYLIDENE]HYDRAZINO]PHENYL] 4,5 DIHYDRO 3(2H) PYRIDAZINONE; 6 [4 [2 [1, 1 BIS N METHYL(ETHYL)CARBAMOYLMETHYLIDENE]HYDRAZINO]PHENYL]4,5 DIHYDRO 3(2H) PYRIDAZINONE DERIVATIVE; AMIDE; ANTIHYPERTENSIVE AGENT; DIGOXIN; UNCLASSIFIED DRUG;

EID: 77949908899     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-010-2222-x     Document Type: Article
Times cited : (23)

References (24)
  • 2
    • 0021285593 scopus 로고
    • 4,5-Dihydro-6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones: Novel positive inotropic agents for the treatment of congestive heart failure
    • 10.1021/jm00375a001 1:CAS:528:DyaL2cXkvVeksL8%3D 6471063
    • J. A. Bristol I. Sircar W. H. Moos D. B. Evans R. E. Weishaar 1984 4,5-Dihydro-6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones: Novel positive inotropic agents for the treatment of congestive heart failure J. Med. Chem. 27 1099 1101 10.1021/jm00375a001 1:CAS:528:DyaL2cXkvVeksL8%3D 6471063
    • (1984) J. Med. Chem. , vol.27 , pp. 1099-1101
    • Bristol, J.A.1    Sircar, I.2    Moos, W.H.3    Evans, D.B.4    Weishaar, R.E.5
  • 4
    • 77949910412 scopus 로고    scopus 로고
    • Chemical Computing Group Manual of Molecular Operating Environment (MOE), version 2007. 09., Inc. Montreal, Quebec, Canada (2005)
    • Chemical Computing Group Manual of Molecular Operating Environment (MOE), version 2007. 09., Inc. Montreal, Quebec, Canada (2005).
  • 5
    • 0023152230 scopus 로고
    • In search of the digitalis replacement
    • 10.1021/jm00385a001 1:CAS:528:DyaL2sXktlagtg%3D%3D
    • P. W. Erhardt 1987 In Search of the Digitalis Replacement J. Med. Chem. 30 231 237 10.1021/jm00385a001 1:CAS:528:DyaL2sXktlagtg%3D%3D
    • (1987) J. Med. Chem. , vol.30 , pp. 231-237
    • Erhardt, P.W.1
  • 6
    • 0026567135 scopus 로고
    • A novel class of cardiotonic agents: Synthesis and biological evaluation of 5-substituted 3,6-dihydro-thiadiazi-2-ones with cyclic AMP phosphodiesterase inhibiting and myofibrillar calcium seneitizing properties
    • 10.1021/jm00079a022 1:CAS:528:DyaK38XktFChtg%3D%3D 1310113
    • M. Forest P. Lahouratate M. Martin G. Nadler M. J. Quiniou R. G. Zimmermann 1992 A novel class of cardiotonic agents: Synthesis and biological evaluation of 5-substituted 3,6-dihydro-thiadiazi-2-ones with cyclic AMP phosphodiesterase inhibiting and myofibrillar calcium seneitizing properties J. Med. Chem. 35 163 172 10.1021/jm00079a022 1:CAS:528:DyaK38XktFChtg%3D%3D 1310113
    • (1992) J. Med. Chem. , vol.35 , pp. 163-172
    • Forest, M.1    Lahouratate, P.2    Martin, M.3    Nadler, G.4    Quiniou, M.J.5    Zimmermann, R.G.6
  • 7
    • 0023760273 scopus 로고
    • Differential effects of d- and l-pimobendan on cardiac myofilament calcium sensitivity
    • 1:CAS:528:DyaL1MXltV2nug%3D%3D 3183951
    • K. Fujino N. Sperelakio R. J. Solaro 1988 Differential effects of d- and l-pimobendan on cardiac myofilament calcium sensitivity J. Pharmacol. Exp. Ther. 247 519 523 1:CAS:528:DyaL1MXltV2nug%3D%3D 3183951
    • (1988) J. Pharmacol. Exp. Ther. , vol.247 , pp. 519-523
    • Fujino, K.1    Sperelakio, N.2    Solaro, R.J.3
  • 9
    • 0021203814 scopus 로고
    • +) Activated ATPase, A Biochemical link to Digitalis-Induced Inotropy
    • 1:CAS:528:DyaL2MXn 6093155
    • +) Activated ATPase, A Biochemical link to Digitalis-Induced Inotropy Pharmacol. Rev. 36 143 160 1:CAS:528:DyaL2MXn 6093155
    • (1984) Pharmacol. Rev. , vol.36 , pp. 143-160
    • Hansen, O.1
  • 10
    • 0034880796 scopus 로고    scopus 로고
    • Nitric oxide independent effects of tempol on sympathetic nerve activity and blood pressure in normotensive rats
    • X. Hui G. D. Fink A. Chen S. Watts J. J. Galligan 2001 Nitric oxide independent effects of tempol on sympathetic nerve activity and blood pressure in normotensive rats Am. J. Physiol. Heart Circ. Physiol. 281 H975 H980
    • (2001) Am. J. Physiol. Heart Circ. Physiol. , vol.281
    • Hui, X.1    Fink, G.D.2    Chen, A.3    Watts, S.4    Galligan, J.J.5
  • 11
    • 0025108835 scopus 로고
    • Nonsteroidal Cardiotonics, New 4,5-Dihydro-6-(1H-indol-5-yl)-pyridazin- 3(2H)-ones and related compounds with positive inotropic activities
    • 10.1021/jm00172a031 1:CAS:528:DyaK3cXlslWqtb0%3D 2213839
    • A. Mertens W. Friebe B. Müller-Beckmann W. Kampe L. Kling W. Von der saal 1990 Nonsteroidal Cardiotonics, New 4,5-Dihydro-6-(1H-indol-5-yl)- pyridazin-3(2H)-ones and related compounds with positive inotropic activities J. Med. Chem. 33 2870 2875 10.1021/jm00172a031 1:CAS:528:DyaK3cXlslWqtb0%3D 2213839
    • (1990) J. Med. Chem. , vol.33 , pp. 2870-2875
    • Mertens, A.1    Friebe, W.2    Müller-Beckmann, B.3    Kampe, W.4    Kling, L.5    Von Der Saal, W.6
  • 12
    • 0023552639 scopus 로고
    • Cardiotonic agents: Selective inhibitors of Adenosine 3′,5′-cyclic phosphate phosphodiesterase III. Elaboration of a five point model for positive inotropic activity
    • 10.1021/jm00394a006 1:CAS:528:DyaL2sXls1yhtrw%3D 2822927
    • W. H. Moos C. C. Humblet I. Sircar C. Rithner R. E. Weishaar J. A. Bristol A. T. McPhail 1987 Cardiotonic agents: selective inhibitors of Adenosine 3′,5′-cyclic phosphate phosphodiesterase III. Elaboration of a five point model for positive inotropic activity J. Med. Chem. 30 1963 1972 10.1021/jm00394a006 1:CAS:528:DyaL2sXls1yhtrw%3D 2822927
    • (1987) J. Med. Chem. , vol.30 , pp. 1963-1972
    • Moos, W.H.1    Humblet, C.C.2    Sircar, I.3    Rithner, C.4    Weishaar, R.E.5    Bristol, J.A.6    McPhail, A.T.7
  • 14
    • 0023240562 scopus 로고
    • A novel class of cardiotonics, Synthesis and pharmacological properties of [4-(substituted-amino)-phenyl]pyridazinones and related derivatives
    • 10.1021/jm00390a007
    • H. Okushiima A. Narimatsu M. Kobayashi R. Furuya K. Tsuda Y. Kitada 1987 A novel class of cardiotonics, Synthesis and pharmacological properties of [4-(substituted-amino)-phenyl]pyridazinones and related derivatives J. Med. Chem. 30 1157 1161 10.1021/jm00390a007
    • (1987) J. Med. Chem. , vol.30 , pp. 1157-1161
    • Okushiima, H.1    Narimatsu, A.2    Kobayashi, M.3    Furuya, R.4    Tsuda, K.5    Kitada, Y.6
  • 15
    • 77949901269 scopus 로고    scopus 로고
    • P. E. Heckelman C. B. Koch K. J. Roman C. M. Kenny M. R. D'Arecea (eds). Fourteenth edn., Merck and Co., Inc. U.S.A.
    • O'Neil, M. J., Merck Index Encyclopedia of Chemicals, Drugs and Biologicals, Heckelman, P. E., Koch, C. B., Roman, K. J., Kenny, C. M., and D'Arecea, M. R. (ed.), Fourteenth edn., Merck and Co., Inc., U.S.A., pp. 378, 610 and 1281, (2006).
    • (2006) Merck Index Encyclopedia of Chemicals, Drugs and Biologicals , pp. 378
    • O'Neil, M.J.1
  • 17
    • 0039115476 scopus 로고
    • ++ sensitivity of contractile proteins.[Miscellaneous]
    • ++ sensitivity of contractile proteins.[Miscellaneous] Circ. 73 suppl.III III-78 III-8
    • (1986) Circ. , vol.73 , Issue.SUPPL. 3 , pp. 78-88
    • Rüegg, J.C.1
  • 18
    • 0021687326 scopus 로고
    • Effect on contractility of skinned fibres from mammalian heart and smooth muscle by a new benzimidazole derivative, 4,5-Dihydro-6-[2-(4-methoxyphenyl]- 1H-benzimidazol-5-yl]-5-methyl-3(2H)-pyridazinone
    • J. C. Rüegg G. Pfitzer D. Eubler C. Zeugner 1984 Effect on contractility of skinned fibres from mammalian heart and smooth muscle by a new benzimidazole derivative, 4,5-Dihydro-6-[2-(4-methoxyphenyl]-1H-benzimidazol-5- yl]-5-methyl-3(2H)-pyridazinone Arzenium Forsch./Drug Res. 34 1736 1738
    • (1984) Arzenium Forsch./Drug Res. , vol.34 , pp. 1736-1738
    • Rüegg, J.C.1    Pfitzer, G.2    Eubler, D.3    Zeugner, C.4
  • 19
    • 0022349218 scopus 로고
    • Synthesis and Structure activity Relationship of 4,5-Dihydro-6-[4-(1H- imidazol-1-yl)phenyl]-3(2H)-pyridazinones: A new class of positive inotropic agents
    • 10.1021/jm00148a006 1:CAS:528:DyaL2MXls1SntLw%3D 2864447
    • I. Sircar B. L. Duell G. Bobowski J. A. Bristol D. B. Evans 1985 Synthesis and Structure activity Relationship of 4,5-Dihydro-6-[4-(1H-imidazol- 1-yl)phenyl]-3(2H)-pyridazinones: A new class of positive inotropic agents J. Med. Chem. 28 1405 1413 10.1021/jm00148a006 1:CAS:528:DyaL2MXls1SntLw%3D 2864447
    • (1985) J. Med. Chem. , vol.28 , pp. 1405-1413
    • Sircar, I.1    Duell, B.L.2    Bobowski, G.3    Bristol, J.A.4    Evans, D.B.5
  • 20
    • 0024594565 scopus 로고
    • Synthesis and Biological Evaluation of a series of 4,5-Dihydro-6-[2-[4- (1H-imidazol-1-yl)phenyl]ethenyl]-3(2H)-pyridazinones: A novel class of compounds with positive inotropic, antithrombotic, and vasodilatory activities for the treatment of congestive heart failure
    • 10.1021/jm00122a011 1:CAS:528:DyaL1MXlslKjsQ%3D%3D 2536438
    • I. Sircar R. P. Steffen G. Bobowski S. E. Burke R. S. Newton R. E. Weishaar J. A. Bristol D. B. Evans 1989 Synthesis and Biological Evaluation of a series of 4,5-Dihydro-6-[2-[4-(1H-imidazol-1-yl)phenyl]ethenyl]-3(2H)- pyridazinones: A novel class of compounds with positive inotropic, antithrombotic, and vasodilatory activities for the treatment of congestive heart failure J. Med. Chem. 32 342 350 10.1021/jm00122a011 1:CAS:528: DyaL1MXlslKjsQ%3D%3D 2536438
    • (1989) J. Med. Chem. , vol.32 , pp. 342-350
    • Sircar, I.1    Steffen, R.P.2    Bobowski, G.3    Burke, S.E.4    Newton, R.S.5    Weishaar, R.E.6    Bristol, J.A.7    Evans, D.B.8
  • 21
    • 77949894108 scopus 로고    scopus 로고
    • S. C. Sweetman (eds). The Pharmaceutical Press London
    • Sweetman, S. C. (ed.), Martindale, The Complete Drug Reference (thirty-third edn.). The Pharmaceutical Press, London, pp. 955.3, 885.1 and 858.1, (2002).
    • (2002) Martindale, the Complete Drug Reference (Thirty-third Edn.) , pp. 9553
  • 22
    • 0020530105 scopus 로고
    • 6-Aryl-4,5-dihydro-3(2H)-pyridazinones: A new class of compounds with platelet aggregation inhibiting and hypotensive activities
    • 10.1021/jm00360a004 1:CAS:528:DyaL3sXktVGmtbk%3D 6854582
    • M. Thyes H. D. Lehmann J. Gries H. König R. Kretzschmer J. Kunze R. Lebkücher D. Lenke 1983 6-Aryl-4,5-dihydro-3(2H)-pyridazinones: A new class of compounds with platelet aggregation inhibiting and hypotensive activities J. Med. Chem. 26 800 807 10.1021/jm00360a004 1:CAS:528:DyaL3sXktVGmtbk%3D 6854582
    • (1983) J. Med. Chem. , vol.26 , pp. 800-807
    • Thyes, M.1    Lehmann, H.D.2    Gries, J.3    König, H.4    Kretzschmer, R.5    Kunze, J.6    Lebkücher, R.7    Lenke, D.8
  • 23
    • 0021959034 scopus 로고
    • Cardiovascular Effects of the positive inotropic agents pimobendan and sulmazole in vivo
    • J. C. A. Von Meel 1985 Cardiovascular Effects of the positive inotropic agents pimobendan and sulmazole in vivo Arzenium Forsch./Drug Res. 35 284
    • (1985) Arzenium Forsch./Drug Res. , vol.35 , pp. 284
    • Von Meel, J.C.A.1
  • 24
    • 0022357794 scopus 로고
    • Studies aimed at elucidating the mechanism of action of CI-914, a new cardiotonic agent
    • 10.1016/0014-2999(85)90297-3 1:CAS:528:DyaL28Xht1arsro%3D 3004993
    • R. E. Weishaar M. Quade J. A. Schenden D. K. Boyd D. B. Evans 1985 Studies aimed at elucidating the mechanism of action of CI-914, a new cardiotonic agent Eur. J. Pharmacol. 119 205 215 10.1016/0014-2999(85)90297-3 1:CAS:528:DyaL28Xht1arsro%3D 3004993
    • (1985) Eur. J. Pharmacol. , vol.119 , pp. 205-215
    • Weishaar, R.E.1    Quade, M.2    Schenden, J.A.3    Boyd, D.K.4    Evans, D.B.5


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