novel azolylalkylthio, -sulfoxy, and -sulfonyl compounds with antipicornaviral activity

a novel series of azolylalkylthio, -sulfoxy, and-sulfonyl compounds was designed, synthesized, and evaluated for antipicornaviral activity. two compounds (4i and 4 1) exhibited significant activity against various serotypes of human rhinovirus (hrv). it was found that incorporation of hydrophobic azoles such as 3-methylisoxazole or 4-methylthiazole led to increased activity. in addition, activity markedly improved when the size of the thio substituent was increased. oxidation of the thio derivatives to the corresponding sulfoxides and sulfones resulted in less active compounds. 2-[6- [(5- chlorobenzimidazol-2-yl)thio]hexyl]-4-methylthiazole (4 1) was found to exhibit activity against hrv comparable tb disoxaril, and was also effective against the coxsackie b 1 virus