Conformational isomerization of N-(naphthalen-1-yl)-N-(phenyl(quinolin-3-yl)methyl)amide derivatives

Abstract

A series of N-(naphthalen-1-yl)-N-(phenyl(quinolin-3-yl)methyl)amide derivatives were designed and synthesized as anti-Mycobacterium tuberculosis drugs. NMR spectra showed that two conformational isomers of these compounds exist in solution, which is not due to cis-trans isomerization of amide bond. We proposed that the spatial interactions between three large aromatic groups caused the conformational isomerization, which was supported by molecular modeling and X-ray diffraction. N-(naphthalen-1-yl)-N-(phenyl(quinolin-3-yl)methyl)amide, conformational isomerization, NMR, molecular modeling

Determination of Absolute Configurations of Bedaquiline Analogs by Quantum Chemical Electronic Circular Dichroism Calculations and an X‐ray Diffraction Study

“…Our group has focused on the development of potent, selective, and less‐toxic antituberculosis drugs based on bedaquiline and, at the same time, the study of the molecular structures and characterization of related compounds 5–8. As mentioned earlier, the R / S chirality of bedaquiline makes it more active and selective than other isomers.…”