Aryloxyacetamidines of Medicinal Interest

The synthesis of new aryloxyacetamidines of potential medicinal interest as antihypertensives was undertaken. The preparation of the unsubstituted, N-methyl and N,N-dimethyl amidines was carried out by the Pinner synthesis or a modification of this process. The N,N,N′-trimethylaryloxyacetamidines necessitated preparation by another procedure. Fifteen amidines and nine intermediates not previously reported in the literature have been prepared and characterized. 2-Thymoloxyacetamidine, 2-(2,6-xylyloxy)acetamidine, 2-(2,6-dichlorophenoxy)acetamidine, 2-(2,6-dimethoxyphenoxy)acetamidine, 2-benzyloxyacetamidine, and their N-methyl and N,N-dimethyl derivatives were evaluated for their potential cardiovascular effects. None of these compounds showed any potent pharmacological activities in a general screen or when tested as norepinephrine-depleting agents or as adrenergic neuron-blocking agents.