Skip to main content

Chemistry and Structure-Activity Relationships of Cardioactive Steroids

  • Chapter
Cardiac Glycosides

Part of the book series: Handbook of Experimental Pharmacology ((HEP,volume 56 / 1))

Abstract

The possible relationships between the three-dimensional structure of a cardioactive steroid (CAS) and its therapeutic and toxic effects haven been examined repeatedly. The reason for this sustained interest has its roots in the medical use of CAS with the ever-increasing number of the elderly, the narrow therapeutic spectrum, and the wide differences in patient responses to this class of compounds (see this Handbook, Vol. 56/II, Chap. 12). It is hoped eventually to find a lead for the synthesis of specific substances with better cardiotonic activity and less toxicity.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Abraham, N.A., Lefebvre, Y.: US 3′944′541, C.A. 85, 21′728 p (1976)

    Google Scholar 

  • Abraham, N.A., Lefebvre, Y.: US 4′011′12, C.A. 87, 39′738 t (1977)

    Google Scholar 

  • Albrecht, H.P., Kunz, B.: Liebigs Ann. Chem. 1975, 2216–2226

    Google Scholar 

  • Albrecht, H.P., Neugebauer, G.: Ger. Offen. 2′336′445, C.A. 82, 140′395 a (1975)

    Google Scholar 

  • Albrecht, H.P., Neugebauer, G.: Ger. Offen. 2′427′977, C.A. 84, 122′155 j (1976)

    Google Scholar 

  • Albrecht, H.P., Neugebauer, G.: Ger. Offen. 2′517′293, C.A. 86, 140′414 p (1977)

    Google Scholar 

  • Aldous, S., Nation, R., Thomas, R.: Aust. J. Pharm. Sci. N.S. 1, 61–62 (1972)

    CAS  Google Scholar 

  • Angarskaya, M.A.: Farmakol. Toksikol. 9, 24–28 (1974);

    CAS  Google Scholar 

  • Angarskaya, M.A.: Farmakol. Toksikol. C.A. 82, 11′027 h (1975)

    Google Scholar 

  • Baumgarten, J.G.: Die herzwirksamen Glykoside. Leipzig: Thieme 1963

    Google Scholar 

  • Bodem, G., Wirth, K., Zimmer, A.: Arzneim. Forsch. 28, 322–325 (1978)

    CAS  Google Scholar 

  • Boehringer, C.H.: Fr. Demande 2′191′902, C.A. 81, 25′912 j (1974)

    Google Scholar 

  • Boettcher, H., Fischer, K., Proppe, D.: Basic Res. Cardiol. 70, 279–291 (1975)

    Article  CAS  Google Scholar 

  • Boutagy, J., Gelbart, A., Thomas, R.: Aust. J. Pharm. Sci. N.S. 2, 41–46 (1973)

    Google Scholar 

  • Caldwell, R.W., Nash, C.B.: J. Pharmacol. Exp. Ther. 197, 19–26 (1976)

    PubMed  CAS  Google Scholar 

  • Caldwell, R.W., Nash, C.B.: J. Pharmacol. Exp. Ther. 204, 141 (1978)

    PubMed  CAS  Google Scholar 

  • Choay, P., Cordboeuf, E., Deroubaix, E.: Eur. J. Pharmacol. 50, 317–323 (1978)

    Article  PubMed  CAS  Google Scholar 

  • Cohnen, E.: Ger. Offen. 2′548′525, C.A. 87, 102′606 r (1977a)

    Google Scholar 

  • Cohnen, E.: Ger. Offen. 2′558′208, C.A. 87, 152′524 h (1977b)

    Google Scholar 

  • Cook, L.S., Caldwell, R.W., Nash, C.B.: Arch. Int. Pharmacodyn. 227, 220–232 (1977)

    PubMed  CAS  Google Scholar 

  • Deghenghi, R.: Synthetic cardenolides and related products. In: Chemistry of natural products, Vol. 6. London: Butterworths 1970

    Google Scholar 

  • Dittrich, F., Megges, R., Portius, H.J., Repke, K.: Ger. (East) 94′616, C.A., 79, 42′775 t (1973)

    Google Scholar 

  • Dittrich, F., Megges, R., Portius, H., Repke, K.: Ger. (East) 108′ 291, C.A. 83, 10′737 y (1975)

    Google Scholar 

  • Dittrich, F., Repke, K.R.H.: Experientia Suppl. 23, 249–254 (1976)

    Google Scholar 

  • Dransfeld, H., Greeff, K.: Naunyn-Schmiedebergs Arch. Exp. Path. Pharmacol. 249, 425–431 (1964)

    CAS  Google Scholar 

  • Dransfeld, H., Galetke, E., Greeff, K.: Arch. Int. Pharmacodyn. 166, 342–349 (1967)

    PubMed  CAS  Google Scholar 

  • Eberlein, W., Nickl, J., Heider, J., Dahms, G., Machleidt, H.: Ber. Dtsch. Chem. Ges. 105, 3686–3694 (1972)

    CAS  Google Scholar 

  • Eberlein, W., Heider, J., Machleidt, H.: Ber. Dtsch. Chem. Ges. 107, 1275–1284 (1974)

    CAS  Google Scholar 

  • Foussard-Blanpin, O., Hubert, F., Choay, P., Leboeuf, M.: Ann. Pharm. Fr. 31, 593–600 (1973)

    PubMed  CAS  Google Scholar 

  • Fritsch, W., Haede, W., Radscheit, K., Stache, U., Inhoffen, H.H., Kreiser, W., Warneke, H.U.: Ger. Offen. 2′361′059, C.A. 83, 206′484 h (1975)

    Google Scholar 

  • Fullerton, D.S., Pankaskie, M.C., Ahmed, K., From, A.H.L.: J. Med. Chem. 19, 1330–1333 (1976)

    Article  PubMed  CAS  Google Scholar 

  • Fullerton, D.S., Gilman, T.M., Pankaskie, M.C., Ahmed, K., From, A.H.L., Duax, W.L., Rohrer, D.C.: J. Med. Chem. 20, 841–844 (1977)

    Article  PubMed  CAS  Google Scholar 

  • Galel, E.E., Kandil, A.M., Abdel-Latif, M., Khedr, T., Rashad, T., Khafagy, S.M.: J. Drug Res. 6, 63–71 (1974);

    Google Scholar 

  • Galel, E.E., Kandil, A.M., Abdel-Latif, M., Khedr, T., Rashad, T., Khafagy, S.M.: J. Drug Res. C.A. 83, 90944 b (1975)

    Google Scholar 

  • Gault, M.H., Charles, J.D., Sugden, D.L., Kepkay, D.C.: J. Pharm. Pharmacol. 29, 27–32 (1977)

    Article  PubMed  CAS  Google Scholar 

  • Guentert, T.: Dissertation Universität Basel 1975

    Google Scholar 

  • Guentert, T.W., Linde, H.H.A., Ragab, M.S., Spengel, S.: Helv. 61, 977–983 (1978)

    Article  CAS  Google Scholar 

  • Hauser, E., Boffo, U., Meister, L., Sawlewicz, L., Linde, H.H.A., Meyer, K.: Helv. 56, 2782–2795 (1973)

    Article  CAS  Google Scholar 

  • Haustein, K.-O., Markwardt, F., Repke, K.R.H.: Eur. J. Pharmacol. 10, 1–10 (1970)

    Article  PubMed  CAS  Google Scholar 

  • Haustein, K.-O., Hauptmann, J.: Pharmacology 11, 129–138 (1974)

    Article  PubMed  CAS  Google Scholar 

  • Henderson, F.G., Chen, K.K.: J. Med. Chem. 8, 577–579 (1965)

    Article  PubMed  CAS  Google Scholar 

  • Isaac, O., Posselt, K., Uthemann, H.: Ger. Offen. 2′513′370, C.A. 84, 44′613 r (1976)

    Google Scholar 

  • Ishikawa, N., Tsuru, H., Shigei, T., Anjyo, T., Okada, M.: Experientia 30, 1308–1310 (1974)

    Article  PubMed  CAS  Google Scholar 

  • Kaiser, F., Schaumann, W., Stach, K., Voigtländer, W.: Ger. Offen. 2′233′147, C.A. 80, 96′230 a (1974)

    Google Scholar 

  • Kaiser, F., Schaumann, W., Stach, K., Voigtländer, W.: Ger. Offen. 2′550′354, C.A. 87, 102′608 t (1977)

    Google Scholar 

  • Kimble, M.A., Elenbaas, R.M.: J. Am. Pharm. Ass. N.S. 14, 362–375 (1974)

    CAS  Google Scholar 

  • Kovafikovâ, A., Kolârovâ, H., Pitra, J.: Experientia 20, 263–264 (1964)

    Article  Google Scholar 

  • Kroneberg, G., Meyer, K.H., Schraufstätter, E., Schütz, S., Stoepel, K.: Naturwissenschaften 51, 192–193 (1964)

    Article  CAS  Google Scholar 

  • Lindig, C., Schmidt, H.J., Repke, K.: Ger. (East) 110′263, C.A. 83, 179′415 c (1975)

    Google Scholar 

  • Lindig, C., Repke, K.: Ger. (East) 116′226, C.A. 85,21′729 q (1976 a)

    Google Scholar 

  • Lindig, C., Repke, K.: Ger. (East) 116′227, C.A. 85, 21′730 h (1976b)

    Google Scholar 

  • Lindig, C., Repke, K.: Ger. (East) 116′613, C.A. 85, 46′966 c (1976c)

    Google Scholar 

  • Lindig, C., Repke, K.: Ger. (East) 116′614, C.A. 85, 46′965 b (1976d)

    Google Scholar 

  • Lindig, C., Repke, K.: Ger. (East) 119′042, C.A. 86, 90′148 g (1977)

    Google Scholar 

  • Luchi, R.J., Conn, H.L.: Prog. Cardiovasc. Dis. 7, 336–359 (1965)

    Article  CAS  Google Scholar 

  • Megges, R., Franke, R., Streckenbach, B., Kammann, G., Repke, K.: US 3′806′502, C.A. 81, 25′913 k (1974)

    Google Scholar 

  • Megges, R., Timm, H., Dittrich, F., Portius, J.H., Repke, K.: Ger. (East) 109′869, C.A. 83, 179′414 b (1975a)

    Google Scholar 

  • Megges, R., Timm, H., Thiemann, P., Dittrich, F., Franke, P., Portius, H., Repke, K.: Ger. (East) 109′622, C.A. 83, 59′166 a (1975b)

    Google Scholar 

  • Megges, R., Timm, H., Portius, H.J., Franke, P., Hintsche, R., Repke, K.: Ger. (East) 126′092, C.A. 88,152′861 m (1978 a)

    Google Scholar 

  • Megges, R., Timm, H., Portius, H.J., Franke, P., Hintsche, R., Repke, K.: Ger. (East) 126′093, C.A. 88,170′392 p (1978 b)

    Google Scholar 

  • Megges, R., Timm, H., Portius, H.J., Glusa, E., Repke, K.: Ger. (East) 129′795, C.A. 89,147′194 n (1978 c)

    Google Scholar 

  • Mendez, R., Pastelin, G., Kabela, E.: J. Pharmacol. Exp. Ther. 188, 189–197 (1974)

    PubMed  CAS  Google Scholar 

  • Meyer, K.: Heiv. 35, 2444–2469 (1952)

    Article  CAS  Google Scholar 

  • Meyer, K.: Planta Medica, Suppl. 4/1971, 1–33

    Google Scholar 

  • Meyer, K.: Swiss 559′219, C.A. 83, 28′459 u (1975)

    Google Scholar 

  • Meyer, K.: Swiss 565′202, C.A. 84, 59′879 f (1976)

    Google Scholar 

  • Meyer, K.: Swiss 583′255, C.A. 87, 6′266 j (1977)

    Google Scholar 

  • Naidoo, B.K., Witty, T.R., Remers, W.A., Besch, H.R.: J. Pharm. Sci. 63, 1391–1394 (1974)

    Article  PubMed  CAS  Google Scholar 

  • Nishie, K., Fitzpatrick, T.J., Swain, A.P., Keyl, A.C.: Chem. Path. Pharmacol., R.C. 15, 601–607 (1976)

    CAS  Google Scholar 

  • Okada, M., Saito, Y.: Chem. Pharm. Bull. 15, 352–353 (1967)

    PubMed  CAS  Google Scholar 

  • Okada, M., Saito, Y.: Chem. Pharm. Bull. 16, 2223–2227 (1968)

    CAS  Google Scholar 

  • Okada, M., Anjyo, T.: Chem. Pharm. Bull. 23, 2039–2043 (1975)

    PubMed  CAS  Google Scholar 

  • Patnaik, G.K., Dhawan, B.N.: Arzneim. Forsch. 28, 1095–1099 (1978)

    CAS  Google Scholar 

  • Patnaik, G.K., Koehler, E.: Arzneim. Forsch. 28, 1368–1372 (1978)

    CAS  Google Scholar 

  • Peterson, R.: Ger. Offen. 2′603′046, C.A. 87, 202′044 z (1977)

    Google Scholar 

  • Ragab, M.S., Linde, H.H.A., Meyer, K.: Heiv. 45, 1794–1799 (1962)

    Article  CAS  Google Scholar 

  • Repke, K.R.H.: Pharmazie 27, 693–701 (1972)

    PubMed  CAS  Google Scholar 

  • Saito, Y., Kanemasa, Y., Okada, M.: Chem. Pharm. Bull. 18, 629–631 (1970)

    CAS  Google Scholar 

  • Sawlewicz, L., Weiss, E., Linde, H.H.A., Meyer, K.: Helv. 55, 2452–2460 (1972)

    Article  CAS  Google Scholar 

  • Schaumann, W., Dietmann, K., Bartsch, W., Kaiser, F., Voigtländer, W.: Ger. Offen. 2′546′779, C.A. 87, 39′772 z (1977)

    Google Scholar 

  • Shigei, T., Katori, M., Murase, H., Imai, S.: Experientia 20, 572–573 (1964)

    Article  PubMed  CAS  Google Scholar 

  • Shigei, T., Mineshita, S.: Experientia 24, 466–467 (1968)

    Article  PubMed  CAS  Google Scholar 

  • Shigei, T., Tsuru, H., Saito, Y., Okada, M.: Experientia 29, 449–450 (1973)

    Article  PubMed  CAS  Google Scholar 

  • Siebeneick, H.U., Hoffmann, W.: J. Med. Chem. 21, 1310–1312 (1978)

    Article  PubMed  CAS  Google Scholar 

  • Stache, U., Haede, W., Fritsch, W., Radscheit, K., Lindner, E.: Ger. Offen. 2′013′032, C.A. 76, 14′816 b (1972)

    Google Scholar 

  • Stache, U., Fritsch, W., Haede, W., Lindner, E.: Ger. Offen. 2′254′060, C.A. 81,37′778 h (1974 a)

    Google Scholar 

  • Stache, U., Radscheit, K., Fritsch, W., Haede, W.: Liebigs Ann. Chem. 1974 b,608–620

    Google Scholar 

  • Stache, U., Fritsch, W., Haede, W., Radscheit, K.: Liebigs Ann. Chem. 1977, 1461–1474

    Google Scholar 

  • Takiura, K., Yuki, H., Okamoto, Y., Takai, H., Honda, S.: Chem. Pharm. Bull. 22, 2263–2269 (1974)

    PubMed  CAS  Google Scholar 

  • Tamm, C.: Proc. 1st International Pharmacol. Meeting, Volume 3, 11–26, Stockholm Oxford: Pergamon Press 1963

    Google Scholar 

  • Thomae, K.: Fr. Demande 2′199′987, C.A. 83, 59′227 w (1975)

    Google Scholar 

  • Thomas, R., Boutagy, J., Gelbart, A.: J. Pharm. Sci. 63, 1649–1683 (1974)

    Article  PubMed  CAS  Google Scholar 

  • Toida, S., Matsuura, S., Hidano, T., Tanihata, T., Ito, R.: Toho Igakkai Zasshi 23,198–202 (1976)

    CAS  Google Scholar 

  • Toida, S., Matsuura, S., Hidano, T., Tanihata, T., Ito, R.: Toho Igakkai Zasshi C.A. 85, 104′093 d (1976)

    Google Scholar 

  • Tsuru, H., Ishikawa, N., Shigei, T., Anjyo, T., Okada, M.: Experientia 31, 955–956 (1975)

    Article  PubMed  CAS  Google Scholar 

  • Tsuru, H., Ishikawa, N., Shigei, T., Anjyo, T., Okada, M.: Jpn. J. Pharmacol. 27, 799–805 (1977)

    Article  PubMed  CAS  Google Scholar 

  • Voigtländer, W., Kaiser, F., Schaumann, W., Stach, K.: Ger. Offen. 2′418′127, C.A. 84, 59′963 d (1976a)

    Google Scholar 

  • Voigtländer, W., Kaiser, F., Schaumann, W., Stach, K.: Ger. Offen. 2′433′563, C.A. 84, 150′934 f (1976b)

    Google Scholar 

  • Voigtländer, W., Kaiser, F., Schaumann, W., Stach, K.: Ger. Offen. 2′457′219, C.A. 85, 124′316 g (1976c)

    Google Scholar 

  • Voigtländer, W., Kaiser, F., Schaumann, W.: Ger. Offen. 2′614′046, C.A. 88, 23′346 y (1978)

    Google Scholar 

  • Wagner, F., Lang, S., Kreiser, W.: Ber. Dtsch. Chem. Ges. 109, 3304–3317 (1976)

    CAS  Google Scholar 

  • Witty, T.R., Remers, W.A., Besch, H.R.: J. Pharm. Sci. 64, 1248–1250 (1975)

    Article  PubMed  CAS  Google Scholar 

  • Yamauchi, T., Abe, F., Takahashi, M.: Tetrahedron Letters 1976, 1115–1116

    Google Scholar 

  • Yamauchi, T., Abe, F.: Tetrahedron Letters 1978, 1825–1828

    Google Scholar 

  • Zürcher, W., Weiss-Berg, E., Tamm, C.: Heiv. 52, 2449–2458 (1969)

    Article  Google Scholar 

Download references

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1974 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Güntert, T.W., Linde, H.H.A. (1974). Chemistry and Structure-Activity Relationships of Cardioactive Steroids. In: Greeff, K. (eds) Cardiac Glycosides. Handbook of Experimental Pharmacology, vol 56 / 1. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-68163-9_2

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-68163-9_2

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-68165-3

  • Online ISBN: 978-3-642-68163-9

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics