Adamantane derivatives of biological interest. Synthesis and antiviral activity of 2-(1-adamantyl)imidazole derivatives.
The methods of synthesis and antiviral evaluation of 2-(1-adamantyl)imidazole (2a), N-methyl-2-(1-adamantyl)imidazole (2b) and 2-(1-adamantyl)benzimidazole (3a) are reported. These compounds are prepared by the selective homolytic substitution reaction by the adamantyl radical (Ad.) on the C-2 carbon atom of the heterocycles. Ad. radicals were generated by oxidative decarboxylation of 1-adamantyl carboxylic acid. Antiviral activities compounds 2a, 2b and 3a were tested in chick embryos against A-2 Victoria virus. Compounds 2a and 2b showed significant antiviral activity, whereas compound 3a was found inactive.
D000218:Adamantane / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D002642:Chick Embryo; D005260:Female; D009980:Influenza A virus / Q000187:drug effects; D007928:Lethal Dose 50; D008297:Male; D051379:Mice; D009976:Orthomyxoviridae Infections / Q000188:drug therapy*
C028919:2-(1-adamantyl)benzimidazole; C028918:2-(1-adamantyl)imidazole; C028920:N-methyl-2-(1-adamantyl)imidazole; D000218:Adamantane