Synthesis and biological activities of novel chiral fluorinated β-carboline derivatives

A series of unreported chiral β-carbolines 4 with trifluoromethyl group at position-1 and chiral carboxamide chains or amino acid ester chains at position-3 has been designed and synthesized. The results of bioassay in vitro show that compounds 4e, 4i and 4k show 78.8%, 84.0% and 78.9% inhibition on monoamine oxidase, in 1 mmol/L, respectively, and compound 4e also exhibit 60.9% inhibitory activity on tumor lung cell A-549 in 10−5 mmol/L. In view of different configuration, the inhibitory activity on monoamine oxidase of S-enantiomer of the target compound is better than that of R-enantiomer.