(Bio)isosteres of ortho- and meta-substituted benzenes
H Erik Diepers,
Johannes C L Walker
Abstract:Saturated bioisosteres of substituted benzenes offer opportunities to fine-tune the properties of drug candidates in development. Bioisosteres of para-benzenes, such as those based on bicyclo[1.1.1]pentane, are now very common and can be used to increase aqueous solubility and improve metabolic stability, among other benefits. Bioisosteres of ortho- and meta-benzenes were for a long time severely underdeveloped by comparison. This has begun to change in recent years, with a number of potential systems being re… Show more
Cyclobutadien, der kleinste Antiaromat, ist sehr reaktiv. Es herzustellen und präparativ zu nutzen ist nicht einfach, aber der Aufwand lohnt sich: Cyclobutadien eignet sich zum Beispiel für [4+2]‐Cycloadditionen, eine Cuban‐ und eine Naturstoffsynthese.
Cyclobutadien, der kleinste Antiaromat, ist sehr reaktiv. Es herzustellen und präparativ zu nutzen ist nicht einfach, aber der Aufwand lohnt sich: Cyclobutadien eignet sich zum Beispiel für [4+2]‐Cycloadditionen, eine Cuban‐ und eine Naturstoffsynthese.
Recently, many saturated bioisosteres of benzene ring have been developed, and their application in drug development has been evaluated. Most of these are caged hydrocarbons, which have rigid skeletons and three-dimensional spaces. Recent efforts to synthesize these caged hydrocarbons have enabled access to multi-functionalized congeners that are expected to be (bio)isosteres of multi-functionalized benzenes. This review article summarizes recently reported methods to obtain multi-functionalized (typically more than disubstituted) caged hydrocarbons.
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