Synthesis and antiviral activity of new adamantane derivatives

New pyrazoles; 1,2,4-triazoles; β- and γ-glycols; amidrazones; and amines of the adamantane series have been synthesized. Their activity with respect to smallpox vaccine virus has been studied. High anti-smallpox activity was observed for ethyl-3-(1-adamantyl)-5-(4-methylphenyl)-1H-pyrazole-4-carboxylate (VI) and 1,4-bis(1-adamantyl)-1,4-butanediol (XII).