Romagnoli, Romeo published the artcileCinnamic acid derivatives linked to arylpiperazines as novel potent inhibitors of tyrosinase activity and melanin synthesis, Related Products of catalysis-chemistry, the publication is European Journal of Medicinal Chemistry (2022), 114147, database is CAplus and MEDLINE.
A novel series of twenty-seven cinnamides constituted by cinnamic acid derivatives liked to 1-aryl piperazines I (R1 = 4-F, 3-Cl, 3,4-diF, etc.; R2 = 4-Cl, 4-NO2, 3-OMe, etc.) were synthesized and evaluated for their diphenolase inhibitory activity of mushroom tyrosinase. Among them, the presence of a 3-chloro-4-fluorophenyl moiety at the N-1 position of piperazine ring was essential for a potent tyrosinase inhibitory effect, compounds I (R1 = 3-Cl, 4-F; R2 = 3-NO2) and I (R1 = 3-Cl, 4-F; R2 = 2-Cl, 3-OMe) as the most potent compounds of the series, with IC50 of 0.16 and 0.12¦ÌM, resp., resulting much active than kojic acid, whose IC50 value was 17.76 mM. The mol. docking to the active site of the enzyme has been also performed to investigate the nature of enzyme-inhibitor interactions. Furthermore, for selected highly active compounds, their ability to inhibit melanogenesis in the A375 human melanoma cells and in vivo zebrafish model was also evaluated. One of the most potent compounds of series I (R1 = 3-Cl, 4-F; R2 = 2-Cl, 3-OMe) significantly reduced the pigmentation of zebrafish at 50¦ÌM, unfortunately showing 100% mortality in the Fish Embryo Acute Toxicity (FET) test at the same concentration, Moreover, the zebrafish assay reveals that also I (R1 = 3-Cl, 4-F; R2 = 3-NO2, 4-OMe) (IC50:0.51¦ÌM against mushroom tyrosinase) effectively reduces melanogenesis with no acute toxicity effects and it could be proposed as potential candidate to treat tyrosinase-mediated hyperpigmentation.
European Journal of Medicinal Chemistry published new progress about 1772-76-5. 1772-76-5 belongs to catalysis-chemistry, auxiliary class Benzenes, name is (E)-3-(3-Nitrophenyl)acrylic acid, and the molecular formula is C9H7NO4, Related Products of catalysis-chemistry.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia