Letter | Published:

Isomeric O-Methyl Ethers of Ethyl di-(4-hydroxycoumarinyl-3)-Acetate (the Anti-coagulant Drug Pelentane or Thromexane)

Abstract

DURING work on the dependence of anticoagulant activity of the 4-hydroxycoumarine derivaties on chemical structure, it has been found, on the basis of infra-red and ultra-violet absorption spectra and the study of methylation products1–3, that ethyl di-(4–hydroxycoumarinyl-3)-acetate (I, pelentane) and 3,3′-methylen bis-(4-hydroxycoumarine), (II, dicoumarol) show tautomeric behaviour similar to that of the derivatives of the 2-hydroxychromone (III). This equilibrium was first described by Arndt4 in 4-hydroxycoumarine (IV). The above-mentioned equilibrium is considerably more pronounced in the bis derivatives than in 4-hydroxycoumarine itself.

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References

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    Knobloch, E., Kakáč, B., and Mácha, F., Chem. Listy, 46, 416 (1952).

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    Fučik, K., Procházka, Ž, and Štrof, J., Chem. Listy, 45, 488 (1951).

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