1.
Am J Med
; 134(7): 827-828, 2021 07.
Artículo
en Inglés
| MEDLINE
| ID: mdl-33773970
2.
ACS Med Chem Lett
; 4(6): 514-6, 2013 Jun 13.
Artículo
en Inglés
| MEDLINE
| ID: mdl-24900702
RESUMEN
Susceptibility to metabolism is a common issue with the tert-butyl group on compounds of medicinal interest. We demonstrate an approach of removing all the fully sp(3) C-Hs from a tert-butyl group: replacing some C-Hs with C-Fs and increasing the s-character of the remaining C-Hs. This approach gave a trifluoromethylcyclopropyl group, which increased metabolic stability. Trifluoromethylcyclopropyl-containing analogues had consistently higher metabolic stability in vitro and in vivo compared to their tert-butyl-containing counterparts.