Syntheses of (14 beta,15 beta,16 beta,17 alpha)- and (14 beta,15 alpha,16 alpha,17 alpha)-1,3,5(10)-estratriene-2,3,14,15,16,17- hexaols, possible candidates for the Inagami--Tamura endogenous digitalis-like factor, and their activity.
Structures are proposed for the Inagami-Tamura endogenous digitalis-like factor (EDLF), and two possible candidates, (14 beta,15 beta,16 beta,17 alpha)- and (14 beta,15 alpha,16 alpha,17 alpha)-2,3,14,15,16,17-hexahydroxy-1,3,5(10)-estratrienes, were synthesized. Both compounds were potent in inducing a contractile response in isolated rat aorta and guinea pig left atrium.
Sakakibara
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Pharmaceutical Research Laboratories, Kirin Brewery Co., Ltd., Gunma, Japan.
Uchida
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D000818:Animals; D001011:Aorta / Q000187:drug effects; D002298:Cardenolides; D002316:Cardiotonic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D004077:Digoxin; D004964:Estriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D006168:Guinea Pigs; D006325:Heart Atria / Q000187:drug effects; D066298:In Vitro Techniques; D009200:Myocardial Contraction / Q000187:drug effects; D051381:Rats; D012503:Saponins / Q000138:chemical synthesis* / Q000494:pharmacology*; D000254:Sodium-Potassium-Exchanging ATPase / Q000037:antagonists & inhibitors
D002298:Cardenolides; D002316:Cardiotonic Agents; D012503:Saponins; C034504:digoxin-like factors; C099065:estratriene-2,3,14,15,16,17-hexaol; D004077:Digoxin; D000254:Sodium-Potassium-Exchanging ATPase; D004964:Estriol