Synthesis of New Benzylic Ethers of Oximes Derived from 1-Phenyl-pyrazole Compounds

Abstract

In the scope of a research program aiming at the synthesis and pharmacological evaluation of new antithrombotic agents via rational molecular design, we describe in this paper the synthesis of benzyl ethers of aryl-pyrazolic oxime derivatives. Ethers' (2a–2c) and (3a–3c) are derived from 4-formyl-l-N-phenylpyrazole (4), in good yield. Designed as interphenylenic analogues of the ridogrel (1), one expects these compounds to present dual properties, i.e., thromboxane A₂ receptors antagonism and thromboxane synthetase inhibition.

Notes

Purchased from Aldrich Co., Milwaukee, Wiscosin, USA.

Prepared in 70% yield for two steps, from methyl 4-hydroxymethyl benzoate²¹, by reaction with thionyl chloride in dry benzene followed treatment of the benzyl chloride derivative with potassium iodide in THF containing a catalytic amount of 18-crown-6.

ref. 19, p. 566.