RESUMO
In this study, we synthesized 4 methimazole (2-mercapto-1-methylimidazole, MMI) derivatives. The kinetics of inhibition on mushroom tyrosinase by methimazole and its derivatives were investigated. The results indicated that tert-butyl 3-methyl-2-sulfanylidene-2,3-dihydro-1H-imidazole-1-carboxylate (compound 3; 3), 2-mercaptoimidazole (MI; compound 1; 1) and MMI (compound 2; 2) significantly inhibited tyrosinase activity in a dose-dependent manner, exhibiting an IC50 value of 1.50mM, 4.11 mM, and 1.43 mM. However, compound 4 (4), compound 5 (5), and compound 6 (6) exerted no inhibitory effect on mushroom tyrosinase activity. Kinetic analysis indicated that 3 was a noncompetitive tyrosinase inhibitor, whereas both 1 and 2 were exhibited as mixed-type tyrosinase inhibitors. Furthermore, 3 exerted a potent inhibitory effect on intracellular melanin formation in the B16/F10 murine melanoma cells and did not cause cytotoxicity, as 1 and 2 did.
Assuntos
Inibidores Enzimáticos/química , Melaninas/metabolismo , Metimazol/química , Monofenol Mono-Oxigenase/antagonistas & inibidores , Agaricales , Animais , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Inibidores Enzimáticos/síntese química , Inibidores Enzimáticos/toxicidade , Cinética , Metimazol/síntese química , Metimazol/toxicidade , Camundongos , Monofenol Mono-Oxigenase/metabolismoRESUMO
In the title mol-ecule, C(8)H(12)N(2)O(2)S, the imidazole ring forms a dihedral angle of 5.9â (2)° with the mean plane of the carboxyl-ate group. In the crystal, mol-ecules are linked by pairs of N-Hâ¯S hydrogen bonds, forming inversion dimers.
RESUMO
In the title compound, C(13)H(21)N(3)O(4)S, the mean plane of the -N(H)-C(=O)-O- group of the carbamate unit forms a dihedral angle of 64.7â (2)° with the mean plane of the -C-C(=O)-O- group of the ester unit. In the crystal, mol-ecules are linked by N-Hâ¯O=C hydrogen bonds, forming chains along the c-axis direction.