To find chemotherapeutic agents for influenza and adenoviruses, 3-(alkoxyphenoxy)-1, 2-propanediols were synthesized. Among these derivatives, 3-(m-dodecyloxyphenoxy)-1, 2-propanediol possessed a fairly inhibitory effect on the multiplication of the PR-8 strain of influenza virus in chorioallantoic membrane culture. By the primary screening test on the type-1 strain of adenovirus, 3-(p-decyloxyphenoxy)-, 3-(p-dodecyloxyphenoxy)-, 3-(o-hexyloxyphenoxy)-, 3-(o-octyloxyphenoxy)-, 3-(o-decyloxyphenoxy)-, 3-(m-butoxyphenoxy)-, 3-(m-pentyloxyphenoxy)-, 3-(m-hexyloxyphenoxy)-, 3-(m-octyloxyphenoxy)-, 3-(m-decyloxyphenoxy)-, and 3-(m-dodecyloxyphenoxy)-1, 2-propanediols were selected. By the secondary screening test, 3-(o-hexyloxyphenoxy)-, 3-(o-octyloxyphenoxy)-, and 3-(p-dodecyloxyphenoxy)-1, 2-propanediols were found to be effective on 10×TCD
50 of the type-1 of adenovirus. Among these three compounds, 3-(o-hexyloxyphenoxy)-1, 2-propanediol was effective on the type-4 and -6 strains, and 3-(o-octyloxyphenoxy)-1, 2-propanediol was effective on the type-4 strain virus, while 3-(p-dodecyloxyphenoxy)-1, 2-propanediol did not show any effect on the type-2, -3, -4, -6, and -7 strains of adenovirus. These three compounds did not possess any direct action for inactivating adenovirus and it was suggested from the experiments that the effectiveness of the compounds was due to the inhibition of viral multiplication.
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