Biological Evaluation of Isosteric Applicability of 1,3‐Substituted Cuneanes as <i>m</i>‐Substituted Benzenes Enabled by Selective Isomerization of 1,4‐Substituted Cubanes
Kan Fujiwara, Shota Nagasawa, Ryusei Maeyama, Ryosuke Segawa, Noriyasu Hirasawa, Takatsugu Hirokawa, Yoshiharu Iwabuchi
Abstract
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.
Topics & Concepts
IsomerizationChemistryMoietyIsostereStereochemistryIn silicoBenzeneBenzene derivativesCombinatorial chemistryOrganic chemistryChemical synthesisBiochemistryCatalysisGeneIn vitroSynthetic Organic Chemistry MethodsAsymmetric Synthesis and CatalysisFluorine in Organic Chemistry