Tyrosinase Inhibitory Activity of Pyrazole Derivatives

Abstract:

A series of 3,5-substituted-4,5-dihydro-1H-pyrazole-1-carbothioamide derivatives were synthesized. Their structures were determined on the basis of spectroscopic data interpretation and their tyrosinase inhibitory activity was determined. The results showed that compound 2 (at 1.00 mg/mL) exhibits significant tyrosinase inhibitory activity with % inhibition of 91.866 ± 2.086 with L-tyrosine as substrate whereas compound 3 (at 1.00 mg/mL) exhibits significant tyrosinase inhibitory activity with % inhibition of 79.266 ± 0.552 and 89.593 ± 1.015 with L-tyrosine and L-DOPA as substrates. The IC₅₀ values of compounds 2 and 3 were further determined comparing with kojic acid and resveratrol. It was found that IC₅₀ values of compounds 2 and 3 were 0.391 ± 0.017 and 0.259 ± 0.005 mg/mL., with L-tyrosine as substrate, which were lower than those of the standard tyrosinase inhibitory resveratrol (0.965 ± 0.016 mg/mL).

• Periodical: Advanced Materials Research (Volume 506)
• Pages: 194-197
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.506.194
• Online since: April 2012
• Authors: T. Suwunwong, T. Kobkeatthawin, K. Chanawanno, N. Saewan, P. Wisitsak, Suchada Chantrapromma
• Keywords: Chalcones, Kojic Acid, Pyrazoles, Resveratrol, Tyrosinase Inhibition

References

[1] M. Shiino, Y. Watanabe, W. Umezawa: Bioorgan. Med. Chem. Vol. 9 (2001), p.1233.

[2] M.E. Chiari, D.M.A. Vera, S.M. Palacios, M.C. Carpinella: Bioorgan. Med. Chem. Vol. 19 (2011), p.3474.

[3] S.K. Sahu, M. Banerjee, A. Samantray, C. Behera, M.A. Azam: Trop. J. Pharm. Res. Vol. 7 (2) (2008), p.961.

[4] S. Gok, M. M. Demet, A. Ӧzdemir, G. Turan-Zitouni: Med. Chem. Res. Vol. 19 (2010), p.94.

[5] B.P. Bandgar, J.V. Totre, S.S. Gawande, C.N. Khobragade S.C. Warangkar, P.D. Kadam: Bioorgan. Med. Chem. Vol. 18 (2010), p.6149.

[6] N. Saewan, S. Koysomboon, K. Chantrapromma: J. Med. Plants Res. Vol. 5(6) (2011), p.1018.