Nonconjugated hydrocarbons, like bicyclo[1.1.1]pentane, bicyclo[2.2.2]octane, triptycene, and cubane are a unique class of rigid linkers. Due to their similarity in size and shape they are useful mimics of classic benzene moieties in drugs, so-called bioisosteres. Moreover, they also fulfill an important role in material sciences as linear linkers, in order to arrange various functionalities in a defined spatial manner. In this Review article, recent developments and usages of these special, rectilinear systems are discussed. Furthermore, we focus on covalently linked, nonconjugated linear arrangements and discuss the physical and chemical properties and differences of individual linkers, as well as their application in material and medicinal sciences.
Nonconjugated Hydrocarbons as Rigid-Linear Motifs: Isosteres for Material Sciences and Bioorganic and Medicinal Chemistry.
Gemma M Locke,S. Bernhard,M. Senge
Published 2019 in Chemistry
ABSTRACT
PUBLICATION RECORD
- Publication year
2019
- Venue
Chemistry
- Publication date
2019-01-14
- Fields of study
Medicine, Materials Science, Chemistry
- Identifiers
- External record
- Source metadata
Semantic Scholar, PubMed
CITATION MAP
EXTRACTION MAP
CLAIMS
CONCEPTS
- bicyclo[1.1.1]pentane
A compact bicyclic hydrocarbon scaffold discussed as a rigid linker example.
- bicyclo[2.2.2]octane
A bicyclic hydrocarbon scaffold discussed as a rigid linker example.
- bioisosteres
Structural substitutes used to mimic benzene-like motifs in drug design.
- bioorganic and medicinal chemistry
The chemistry area where these scaffolds are considered as drug-relevant structural mimics.
- covalently linked nonconjugated linear arrangements
Linear architectures formed by covalently connecting nonconjugated hydrocarbon units.
- cubane
A cubic polycyclic hydrocarbon scaffold discussed as a rigid linker example.
- individual linkers
The specific linker molecules or scaffolds being compared within the review.
- material sciences
The application area where these linkers are used to arrange functionalities in defined spatial positions.
- nonconjugated hydrocarbons
Hydrocarbon scaffolds lacking extended conjugation that are discussed here as rigid linker frameworks.
- physical and chemical properties
The property set used to compare the different linkers.
- rigid-linear motifs
Approximately linear, rigid structural motifs built from nonconjugated hydrocarbon frameworks.
- triptycene
A polycyclic hydrocarbon scaffold discussed as a rigid linker example.