Synthesis and antiviral activity of sulfonamidobenzophenone oximes and sulfonamidobenzamides.
To find antiviral agents, various sulfonamidobenzophenone oximes (II) were synthesized from the appropriate m-sulfonamidobenzophenones by hydroxylamine reaction. The reaction products were generally obtained as syn/anti mixtures which were separable by fractional crystallization. The anti isomer had more potent antipoliovirus activity than the syn isomer. Various sulfonamidobenzamides (III) which were structurally related to II were synthesized by the reactions of amino-substituted benzamides with sulfuryl chloride or amines with (aminosulfonyl)benzoyl chloride. Antiviral activity was examined by the plaque-inhibition test. Compounds 5, 36, and 69 exhibited strong antipicornavirus activity. The structure-activity relationships are discussed.
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis*; D001549:Benzamides / Q000138:chemical synthesis* / Q000494:pharmacology; D001577:Benzophenones / Q000138:chemical synthesis* / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D002522:Chlorocebus aethiops; D004770:Enterovirus / Q000187:drug effects; D006367:HeLa Cells; D006801:Humans; D007668:Kidney; D008253:Macaca mulatta; D010091:Oximes / Q000138:chemical synthesis / Q000494:pharmacology; D017955:Poliovirus / Q000187:drug effects; D012229:Rhinovirus / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000494:pharmacology; D010948:Viral Plaque Assay; D014776:Virus Cultivation
D000998:Antiviral Agents; D001549:Benzamides; D001577:Benzophenones; D010091:Oximes; D013449:Sulfonamides