Studies on the Hemorrhagic Sweet Clover Disease

Overman, Ralph S.; Stahmann, Mark A.; Huebner, Charles F.; Sullivan, William R.; Spero, Leonard; Doherty, David G.; Ikawa, Miyoshi; Graf, Liselotte; Roseman, Saul; Link, Karl Paul

doi:10.1016/s0021-9258(18)51207-2

Cited by 81 publications

(14 citation statements)

References 15 publications

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“…The results of these preliminary experiments should stimulate research on an economical and practical method of reducing the spoilage of milk by feeding of menadione to milk cows. to bacteriostatic and bactericidal properties of certain compounds (5,9,11,12). Later some of these observations were confirmed and extended (7, 8).…”

Section: Biological Assaymentioning

confidence: 99%

“…Dicumarol has played an important role in human therapy as a valuable agent in preventing coronary thrombosis and postoperative thrombi. Starting in 1940 Link and associates (9,11) synthesized a large series of derivatives of 3,3 '-methylenebis (4-hydroxycoumarin) and 3-substituted 4-hydroxycoumarins in an effort to find one with even better physiological and pharmaceutical properties than Dicumarol for therapeutic use. None proved to be superior to Dicumarol in the rabbit, used as the assay animal.…”

mentioning

confidence: 99%

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Rodenticides, Problems Encountered in the Physicochemical Analysis of Warfarin

Coon¹,

Richter²,

Hein³

et al. 1954

J. Agric. Food Chem.

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Since the anticoagulant rodenticide, warfarin, was registered for general use (1950), commercial concentrates and finished baits have been assayed for warfarin content by physicochemical means.Concentrates and most finished baits presented no particular problem. However, two types of finished baits, one a coated grain and the other a pelletized grain mixture, yielded low results when assayed by the usual method employing a diethyl ether extraction. Substituting a weak alkaline solution for the diethyl ether allowed 90 to 100% recovery of warfarin in these baits. These findings were substantiated by biological assay. Anticoagulant rodenticides had their inception with the isolation, identification, and synthesis of the active principle in spoiled sweet clover hay, which causes a hemorrhagic condition in livestock, particularly cattle, frequently resulting in death (2,9,13). This factor was found to be 3,3 '-methylenebis (4hydroxvcoumarin), later designated as Dicumarol.

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Section: Biological Assaymentioning

confidence: 99%

mentioning

confidence: 99%

Rodenticides, Problems Encountered in the Physicochemical Analysis of Warfarin

Coon¹,

Richter²,

Hein³

et al. 1954

J. Agric. Food Chem.

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show abstract

“…Overman, Stahmann, Huebner, Sullivan, Spero, Doherty, Ikawa, Graf, Roseman, and Link (313) have summarized their extensive studies on the relation of structure to anticoagulant activity among compounds of the 4hydroxycoumarin type. On the basis of a single oral dose assay, they concluded that 3,3,-methylenebis(4-hydroxycoumarin) was the most potent member of this class of substances.…”

Section: K Thyroxinementioning

confidence: 99%

Metabolite Antagonists.

Roblin¹

1946

Chem. Rev.

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“…Since the pioneering discovery of 3,3¢-methylene-bis(4hydroxycoumarin) as the causative agent of the hemorrhagic sweet clover disease of cattle, there has been a surge of interest in the development of novel hypothrombinemic (anticoagulant) agents. 1 Accordingly, a number of structural modifications of the 4-hydroxycoumarin moiety have been performed, including the introduction of an aryl group at the 3-position (1). 2,3 Furthermore, some 3-aryl-4-hydroxycoumarins [e.g., derrusnin (2)] 4a that have been isolated from Leguminosae display strong phytoalexin properties and have proven attractive synthetic targets.…”

mentioning

confidence: 99%