1-Amino-4,4-difluorocyclohexanecarboxylic acid as a promising building block for drug discovery: design, synthesis and characterization

1-Amino-4,4-difluorocyclohexanecarboxylic acid has been designed as a fluorinated analogue of the pharmacologically relevant 1-aminocyclohexanecarboxylic acid. The synthesis has been performed in three steps from a commercially available material in 22% overall yield. An impact of fluorine atoms on conformation, lipophilicity, acidity and fluorescent properties of the amino acid has been studied. Various practical applications of the obtained compound are suggested.

Mykhailiuk P. K.; Starova V.; Iurchenko V.; Shishkina S. V.; Shishkin O. V.; Khilchevskyi O.; Zaporozhets O.
Tetrahedron 2013, 69 (20), 4066-4075
DOI: 10.1016/j.tet.2013.03.072