1,2-Difunctionalized bicyclo[1.1.1]pentanes: Long-sought-after mimetics for <i>ortho</i>/<i>meta</i>-substituted arenes.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 34244445.
- Also identified by DOI 10.1073/pnas.2108881118 and PMC identifier 8285974.
- No licence information is recorded for this record.
- Because redistribution is not established, this page shows the abstract only. Follow the links below for the full text.
Abstract
The development of a versatile platform for the synthesis of 1,2-difunctionalized bicyclo[1.1.1]pentanes to potentially mimic <i>ortho</i>/<i>meta</i>-substituted arenes is described. The syntheses of useful building blocks bearing alcohol, amine, and carboxylic acid functional handles have been achieved from a simple common intermediate. Several <i>ortho-</i> and <i>meta</i>-substituted benzene analogs, as well as simple molecular matched pairs, have also been prepared using this platform. The results of in-depth ADME (absorption, distribution, metabolism, and excretion) investigations of these systems are presented, as well as computational studies which validate the <i>ortho-</i> or <i>meta</i>-character of these bioisosteres.
Medical subject headings
- Hydrocarbons, Aromatic
- Pentanes