Design, synthesis and biological evaluation of 2,4,6-triaminopyrimidine derivatives as tyrosinase inhibitors

Tyrosinase is a copper-dependent monooxygenase enzyme, which is considered as the rate-limiting enzyme in the melanin production pathway. Given this background, melanin increment due to the tyrosinase hyperactivity can give rise to hyperpigmentation disorders, which is followed by wrinkles, skin irritation and melasma in extreme cases. Besides, tyrosinase is regarded as a key agent in the risk of malignant melanoma cancer. Therefore, compounds inhibiting tyrosinase activity are of special interest for clinical medicine and cosmetic industry. Two novel derivatives of 2,4,6-triaminopyrimidine were synthesized and confirmed by C NMR, H NMR, and FTIR. The inhibitory potential was evaluated based on dopaquinone production by an enzyme assay and the absorbance was taken at λ=490nm, spectrophotometrically. The synthesized compounds a and b displayed significant inhibition of tyrosinase with IC50 34.17 μM and 35.37 μM, respectively, and the activities were compared with kojic acid.

کلیدواژه ها:

2 ، 4 ، 6-triaminopyrimidine ، Inhibitor ، Tyrosinase