The Anticoagulant Activity of 3.3’-(p-Alkylthio-Benzylidene)-Bis-4-Hydroxycoumarins and Their Oxidation Products

Summary

The anticoagulant activity of 3.3’-(benzylidene)-bis-4-hydroxycoumarin derivatives has been estimated by one step Quick’s method. The derivatives contained the following groups in the para position of benzylidene residue: NCS- (I), CH₃-S- (II), CH₃-SO-(III), CH₃-S0₂- (IV), C₂H₅-S- (V), C₂H₅-SO- (VI), C₂H₅-S0₂- (VII). All these compounds were much more active than 3.3’-(benzylidene)-bis-4-hydroxycoumarin itself.

Compounds possessing the ethyl chain at the sulphur atom (V, VI, VII) were more active than methyl homologues (II, III, IV). Comparison of the activity of the series of thio-, sulphoxy-, and sulphonyl-derivatives showed that among methyl- and ethyl-derivatives those with the sulphoxy grouping (III, VI) displayed the greatest anticoagulant activity. The action of sulphonyl (IV, VII) and thio-derivatives (II, V) was weaker and shortest. The derivative with the NCS-group (I) possessed a relatively the lowest activity among the investigated compounds. 3.3’-(p-Ethylsulphoxybenzyl-idene)-bis-4-hydroxycoumarin (VI), with distinct biological activity reached about ½ of dicoumarol activity.

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