Synthesis of functionalized 5-(3-R-1-adamantyl)uracils and related compounds |
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Authors: | Alexander Shmailov Elvira Shokova Ivan Vatsouro |
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Institution: | a Department of Chemistry, Moscow State University, Lenin's Hills, Moscow, 119991, Russia b Ivanovsky Institute of Virology, Gamalei 16, Moscow, 123098, Russia |
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Abstract: | Efficient synthetic approaches to functionalized 5-(3-R-1-adamantyl)uracils and related compounds (R=OH, COOH, NH2, etc.) are described. The selective hydroxylation of the adamantane tertiary C-H bonds in 5-(1-adamantyl)uracils with H2SO4 in trifluoroacetic anhydride is used as the key step. Subsequent electrophilic reactions of 5-(3-hydroxy-1-adamantyl)uracils with N- and C-nucleophiles in CF3COOH, H2SO4 or H2SO4/AcOH media yielded derivatives with amide, amino, aryl, carboxy and thiourea groups in the adamantane core. The preliminary evaluation of the antiviral activity revealed that some of the synthesized species display moderate antiviral activity against HSV-1 (SI∼20) in Vero cells. |
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Keywords: | Adamantylated pyrimidines Synthesis Hydroxylation of adamantane derivatives Trifluoroacetic anhydride Trifluoroacetic acid Antiviral activity |
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