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Volumn 41, Issue 16, 1998, Pages 3033-3040

A new approach to the design of novel inhibitors of Na+,K+-ATPase: 17α-substituted seco-D 5β-androstane as cassaine analogues

Author keywords

[No Author keywords available]

Indexed keywords

(3BETA HYDROXY 14 OXO 14,15,5BETA ANDROSTANE) 17ALPHA ACRYLIC ACID, 2 (N,N DIMETHYLAMINO)ETHYL ESTER; (3BETA,4 DIHYDROXY 5BETA,14BETA ANDROSTANE) 17ALPHA ACRYLIC ACID,2 (N,N DIMETHYLAMINO)ETHYL ESTER; ADENOSINE TRIPHOSPHATASE INHIBITOR; ANDROSTANE DERIVATIVE; CASSAINE; DIGITOXIGENIN; UNCLASSIFIED DRUG;

EID: 0032581658     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980108d     Document Type: Article
Times cited : (29)

References (36)
  • 1
    • 0025181375 scopus 로고
    • Digitalis: Its mode of action, receptor and structure activity relationships
    • Academic Press: New York
    • (a) Thomas, R.; Gray, P.; Andrews, J. Digitalis: its mode of action, receptor and structure activity relationships. In Advances in Drug Research; Academic Press: New York, 1990; Vol. 19, pp 311-562.
    • (1990) Advances in Drug Research , vol.19 , pp. 311-562
    • Thomas, R.1    Gray, P.2    Andrews, J.3
  • 3
    • 0029832375 scopus 로고    scopus 로고
    • In search of ideal inotropic steroids: Recent progress
    • Jucker, E., Ed.; Birkhauser Verlag: Basel, Switzerland
    • (c) Repke, K. R. H.; Sweadner, K. J.; Weiland, J.; Megges, R.; Schon, R. In search of ideal inotropic steroids: recent progress. In Progress in Drug Research; Jucker, E., Ed.; Birkhauser Verlag: Basel, Switzerland, 1996; Vol. 47, pp 9-52.
    • (1996) Progress in Drug Research , vol.47 , pp. 9-52
    • Repke, K.R.H.1    Sweadner, K.J.2    Weiland, J.3    Megges, R.4    Schon, R.5
  • 4
    • 0030669282 scopus 로고    scopus 로고
    • Status and prospect of current inotropic agents
    • (d) Repke, K. R. H.; Megges, R. Status and prospect of current inotropic agents. In Exp. Opin. Ther. Pat. 1997, 7, 1297-1306.
    • (1997) Exp. Opin. Ther. Pat. , vol.7 , pp. 1297-1306
    • Repke, K.R.H.1    Megges, R.2
  • 6
    • 0016224910 scopus 로고
    • Synthesis and biological activity of semisynthetic digitalis analogs
    • Thomas, R.; Boutagy, J.; Gelbart, A. Synthesis and biological activity of semisynthetic digitalis analogs. J. Pharm. Sci. 1974, 63, 1649-1683.
    • (1974) J. Pharm. Sci. , vol.63 , pp. 1649-1683
    • Thomas, R.1    Boutagy, J.2    Gelbart, A.3
  • 7
    • 15444354114 scopus 로고    scopus 로고
    • note
    • 1a
  • 8
    • 0030969923 scopus 로고    scopus 로고
    • Synthesis and structure - Activity relationships of 17β-substituted 14β-hydroxysteroid 3-(α-L-rhamnopyranoside)s: Steroids that bind to the digitalis receptor
    • Templeton, J. F.; Ling Y.; Marat, K.; La Bella, F. S. Synthesis and structure - activity relationships of 17β-substituted 14β-hydroxysteroid 3-(α-L-rhamnopyranoside)s: steroids that bind to the digitalis receptor. J. Med. Chem 1997, 40, 1439-1446.
    • (1997) J. Med. Chem , vol.40 , pp. 1439-1446
    • Templeton, J.F.1    Ling, Y.2    Marat, K.3    La Bella, F.S.4
  • 11
    • 0025736572 scopus 로고
    • Chemical models for the chemical nature of endogenous digitalis
    • Repke, K. R. H.; Weiland, J.; Menkes, K. H. Chemical models for the chemical nature of endogenous digitalis. J. Enzyme Inhib. 1991, 5, 25-32.
    • (1991) J. Enzyme Inhib. , vol.5 , pp. 25-32
    • Repke, K.R.H.1    Weiland, J.2    Menkes, K.H.3
  • 18
    • 0030273211 scopus 로고    scopus 로고
    • Digitalis-like compounds: Synthesis and biological evaluation of seco-D and D-homo derivatives
    • Gobbini, M.; Benicchio, A.; Marazzi, G.; Padoani, G.; Torri, M.; Melloni, P. Digitalis-like compounds: synthesis and biological evaluation of seco-D and D-homo derivatives. Steroids 1996, 61, 572-582.
    • (1996) Steroids , vol.61 , pp. 572-582
    • Gobbini, M.1    Benicchio, A.2    Marazzi, G.3    Padoani, G.4    Torri, M.5    Melloni, P.6
  • 19
    • 15444343127 scopus 로고    scopus 로고
    • note
    • 50 = 100 μM).
  • 20
    • 0016130950 scopus 로고
    • Cardenolide analogs. V. Cardiotonic activity of semisynthetic analogs of digitoxigenin
    • (a) Thomas, R.; Boutagy, J.; Gelbart, A. Cardenolide analogs. V. Cardiotonic activity of semisynthetic analogs of digitoxigenin. J. Pharmacol. Exp. Ther. 1974, 191, 219-231. In this paper, the 17α-acrylonitrile is reported to be a weak positive inotropic compound (0.04 relative potency vs digitoxigenin).
    • (1974) J. Pharmacol. Exp. Ther. , vol.191 , pp. 219-231
    • Thomas, R.1    Boutagy, J.2    Gelbart, A.3
  • 21
    • 0006496032 scopus 로고
    • Cardenolide analogues III. Synthesis of C17α- and C17β-(α,β-unsaturated) esters, ketones, nitriles and related derivatives from digitoxigenin
    • (b) Thomas, R.; Boutagy, J.; Gelbart, A. Cardenolide analogues III. Synthesis of C17α-and C17β-(α,β-unsaturated) esters, ketones, nitriles and related derivatives from digitoxigenin. Aust. J. Pharm. Sci. 1973, NS2, 9-20.
    • (1973) Aust. J. Pharm. Sci. , vol.NS2 , pp. 9-20
    • Thomas, R.1    Boutagy, J.2    Gelbart, A.3
  • 23
    • 0016746023 scopus 로고
    • Cardiotonic steroids: Correlation of sodium-potassium adenosine triphosphate inhibition and ionic transport in vitro with inotropic activity and toxicity in dogs
    • Some biological properties of compound 5 have already been reported in the literature, but, to the best of our knowledge, its preparation and chemical properties have not appeared yet. Beard, N. A.; Rouse, W.; Somerville, A. R. Cardiotonic steroids: correlation of sodium-potassium adenosine triphosphate inhibition and ionic transport in vitro with inotropic activity and toxicity in dogs. Br. J. Pharm. 1975, 54, 65-74.
    • (1975) Br. J. Pharm. , vol.54 , pp. 65-74
    • Beard, N.A.1    Rouse, W.2    Somerville, A.R.3
  • 24
    • 0030990878 scopus 로고    scopus 로고
    • An expeditious route to 3β,14β-dihydroxy-5β-androstane-17β-carboxaldehyde
    • Gobbini, M.; Torri, M. An expeditious route to 3β,14β-dihydroxy-5β-androstane-17β-carboxaldehyde. Synth. Commun. 1997, 27, 1115-22.
    • (1997) Synth. Commun. , vol.27 , pp. 1115-1122
    • Gobbini, M.1    Torri, M.2
  • 25
    • 37049080243 scopus 로고
    • Synthesis of 3β,14-dihydroxy-5β,14β-pregnan-20-one C3-derivatives: Ozonolysis of digitoxin and digitoxigenin and their derivatives followed by zinc-acetic acid reduction to the C-21 methyl ketone
    • Templeton, J. F.; Ling Y.; Jin, J.; Boehmer, M. A., Zeglam, T. H.; La Bella, F. S. Synthesis of 3β,14-dihydroxy-5β,14β-pregnan-20-one C3-derivatives: ozonolysis of digitoxin and digitoxigenin and their derivatives followed by zinc-acetic acid reduction to the C-21 methyl ketone. J. Chem. Soc., Perkin Trans. 1 1991, 4, 823-29.
    • (1991) J. Chem. Soc., Perkin Trans. 1 , vol.4 , pp. 823-829
    • Templeton, J.F.1    Ling, Y.2    Jin, J.3    Boehmer, M.A.4    Zeglam, T.H.5    La Bella, F.S.6
  • 27
    • 15444338822 scopus 로고    scopus 로고
    • note
    • 2
  • 29
    • 0003942864 scopus 로고
    • J. Wiley & Sons: New York
    • 2 = +82°), due to the significantly lower population, a decrease in potency compared to digitoxigenin could have been anticipated. Also the favored s-trans conformation of the (C=C-C=O) fragment is consistent with experimental data. See: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; J. Wiley & Sons: New York, 1994; p 622.
    • (1994) Stereochemistry of Organic Compounds , pp. 622
    • Eliel, E.L.1    Wilen, S.H.2
  • 30
    • 15444352434 scopus 로고    scopus 로고
    • note
    • 11,26
  • 31
    • 0016184723 scopus 로고
    • +-ATPase. III. Purification from the outer medula of mammalian kidney after selective removal of membrane components by sodium dodecylsulphate
    • +-ATPase. III. Purification from the outer medula of mammalian kidney after selective removal of membrane components by sodium dodecylsulphate. Biochim. Biophys. Acta 1974, 356, 36-52.
    • (1974) Biochim. Biophys. Acta , vol.356 , pp. 36-52
    • Jørghensen, P.L.1
  • 32
    • 0021232444 scopus 로고
    • +-ATPaSe for different digitalis derivatives
    • +-ATPaSe for different digitalis derivatives. Arzneim. Forsch. 1984, 34, 1314.
    • (1984) Arzneim. Forsch. , vol.34 , pp. 1314
    • Brown, L.1    Erdmann, E.2
  • 34
    • 15444340719 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of seco-D digitalis-like compounds
    • Las Vegas, Nevada, Sept. 7-11, Abstracts of Papers, Part 1, MEDI 033
    • Gobbini, M.; De Munari, S.; Fedrizzi, G.; Padoani, G.; Santagostino, M.; Torri, M.; Melloni, P. Synthesis and biological evaluation of seco-D digitalis-like compounds. 214th ACS National Meeting, Las Vegas, Nevada, Sept. 7-11, 1997, Abstracts of Papers, Part 1, MEDI 033.
    • (1997) 214th ACS National Meeting
    • Gobbini, M.1    De Munari, S.2    Fedrizzi, G.3    Padoani, G.4    Santagostino, M.5    Torri, M.6    Melloni, P.7
  • 35
    • 0000440488 scopus 로고
    • Steroids and related products. XXV. Cardiotonic steroids. II. The synthesis of 17β-substituted 14(15)-unsaturated steroids of the A/B-cis series. Part I
    • Bach, G.; Capitaine, J.; Engel, C. H. Steroids and related products. XXV. Cardiotonic steroids. II. The synthesis of 17β-substituted 14(15)-unsaturated steroids of the A/B-cis series. Part I. Can. J. Chem. 1968, 46, 733-749.
    • (1968) Can. J. Chem. , vol.46 , pp. 733-749
    • Bach, G.1    Capitaine, J.2    Engel, C.H.3
  • 36
    • 33845378961 scopus 로고
    • Zinc-modified cyanoborohydride as a selective reducing agent
    • Kim, S.; Oh, C. H.; Ko, J. S.; Ahn, K. H.; Kim, Y. Zinc-modified cyanoborohydride as a selective reducing agent. J. Org. Chem. 1985, 50, 1927-32.
    • (1985) J. Org. Chem. , vol.50 , pp. 1927-1932
    • Kim, S.1    Oh, C.H.2    Ko, J.S.3    Ahn, K.H.4    Kim, Y.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.