Dataset Information


Organic chemistry. Strain-release amination.

ABSTRACT: To optimize drug candidates, modern medicinal chemists are increasingly turning to an unconventional structural motif: small, strained ring systems. However, the difficulty of introducing substituents such as bicyclo[1.1.1]pentanes, azetidines, or cyclobutanes often outweighs the challenge of synthesizing the parent scaffold itself. Thus, there is an urgent need for general methods to rapidly and directly append such groups onto core scaffolds. Here we report a general strategy to harness the embedded potential energy of effectively spring-loaded C-C and C-N bonds with the most oft-encountered nucleophiles in pharmaceutical chemistry, amines. Strain-release amination can diversify a range of substrates with a multitude of desirable bioisosteres at both the early and late stages of a synthesis. The technique has also been applied to peptide labeling and bioconjugation.

SUBMITTER: Gianatassio R 

PROVIDER: S-EPMC4730898 | BioStudies | 2016-01-01

REPOSITORIES: biostudies

Similar Datasets

2019-01-01 | S-EPMC6788743 | BioStudies
2018-01-01 | S-EPMC6001403 | BioStudies
2017-01-01 | S-EPMC5334783 | BioStudies
2019-01-01 | S-EPMC6604700 | BioStudies
2020-01-01 | S-EPMC7318212 | BioStudies
2020-01-01 | S-EPMC7148169 | BioStudies
2015-01-01 | S-EPMC4654962 | BioStudies
2016-01-01 | S-EPMC5102008 | BioStudies
2019-01-01 | S-EPMC6841681 | BioStudies
2018-01-01 | S-EPMC6021532 | BioStudies