RESUMO
A catalytic method for the C-H alkylation of cubanes is described. Some hydrogen atom transfer catalysts enable the direct abstraction of a hydrogen atom from the C-H bond of cubanes, followed by conjugate addition of the generated cubyl radicals to electron-deficient alkenes. Synthetic applications of the functionalization method developed are also described.
RESUMO
We herein evaluate a biological applicability of 1,3-substituted cuneanes as an isostere of m-substituted benzenes based on its structural similarity. An investigation of a method to obtain 1,3-substituted cuneanes by selective isomerization of 1,4-substituted cubanes enables this attempt by giving a key synthetic step to obtain a cuneane analogs of pharmaceuticals having m-substituted benzene moiety. Biological evaluation of the synthesized analogs and in silico study of the obtained result revealed a potential usage of cuneane skeleton in medicinal chemistry.
Assuntos
Derivados de Benzeno , Benzeno , Benzeno/química , Isomerismo , Derivados de Benzeno/químicaRESUMO
A novel method of introducing an oxygen functionality into a cubane core was developed using a transition-metal-catalyzed directed acetoxylation methodology via C-H activation. The obtained compounds were derivatized into cubane analogues of pharmaceutically relevant structural motifs, namely, acetylsalicylic acid and coumarin motifs, which could potentially act as bioisosteres of these scaffolds.