Synthesis, Stereochemical Separation, and Biological Evaluation of Selective Inhibitors of Human MAO-B: 1-(4-Arylthiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazines

Chimenti, Franco; Secci, Daniela; Bolasco, Adriana; Chimenti, Paola; Granese, Arianna; Carradori, Simone; Yáñez, Matilde; Orallo, Francisco; Sanna, M. Luisa; Gallinella, Bruno; Cirilli, Roberto

doi:10.1021/jm100120s.s001

jm100120s_si_001.pdf (315.45 kB)

Synthesis, Stereochemical Separation, and Biological Evaluation of Selective Inhibitors of Human MAO-B: 1-(4-Arylthiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazines

journal contribution

posted on 2010-09-09, 00:00 authored by Franco Chimenti, Daniela Secci, Adriana Bolasco, Paola Chimenti, Arianna Granese, Simone Carradori, Matilde Yáñez, Francisco Orallo, M. Luisa Sanna, Bruno Gallinella, Roberto Cirilli

Novel 1-(4-arylthiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazine derivatives have been investigated for their ability to inhibit selectively the activity of the human B isoform of monoamine oxidase. These compounds were obtained as racemates and (R)-enantiomers by a stereoconservative synthetic pattern in high yield and enantiomeric excess. The (S)-enantiomers of the most active derivatives have been separated by enantioselective HPLC. All compounds showed selective activity against hMAO-B with IC₅₀ ranging between 21.90 and 0.018 μM.