Synthesis of Fluorinated N- Benzylaniline Derivatives and Evaluations on Anti-Tyrosinase and Anti-Melanogenic Activities

Kanokwan Singpanna; Panupun Limpachayaporn; Monrudee Sukma; Anan Athipornchai; Nopparat Nuntharatanapong

doi:10.4028/p-92oxa7

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HomeKey Engineering MaterialsKey Engineering Materials Vol. 914Synthesis of Fluorinated N- Benzylaniline...

Synthesis of Fluorinated N- Benzylaniline Derivatives and Evaluations on Anti-Tyrosinase and Anti-Melanogenic Activities

Abstract:

Melasma, freckles, age spots, and acne scars are common aesthetic problems resulted from melanin overproduction. This study aimed to develop new skin depigmenting compounds and characterize on melanin inhibition activities. The fluorinated N-benzylaniline derivatives were synthesized and evaluated for their in vitro anti-tyrosinase activity. Derivatives with p-fluorine monosubstition, N-(4-fluorobenzyl)-3-fluoro-4-methoxyaniline (3d), was the most potent inhibitor against mushroom tyrosinase with 75.4 ± 0.34 % inhibition at 500 µM which was as potent as the positive control, kojic acid. Furthermore, compound 3d exhibited superior anti-melanogenic activity in α-MSH-induced B16F10 murine melanoma cells, compared to kojic acid. Therefore, N-(4-fluorobenzyl)-3-fluoro-4-methoxyaniline (3d) was proposed as a new agent effective against skin hyperpigmentation.

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Key Engineering Materials (Volume 914)

Pages:

87-92

DOI:

https://doi.org/10.4028/p-92oxa7

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Online since:

March 2022

Authors:

Kanokwan Singpanna, Panupun Limpachayaporn, Monrudee Sukma, Anan Athipornchai, Nopparat Nuntharatanapong*

Keywords:

Anti-Melanogenic Activity, Anti-Tyrosinase Activity, Melanin, N- Benzylaniline Derivatives, Skin Whitening Agent, Tyrosinase

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References

[1] M. N. Masum, K. Yamauchi, T. Mitsunaga, Tyrosinase inhibitors from natural and synthetic sources as skin-lightening agents, Rev Agric Sci. 7 (2019) 41-58.

DOI: 10.7831/ras.7.41

Google Scholar

[2] T. S. Chang, An updated review of tyrosinase inhibitors, Int J Mol Sci. 10 (2009) 2440-2475.

Google Scholar

[3] Y. J. Kim, H. Uyama, Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future, Cell Mol Life Sci. 62 (2005) 1707-1723.

DOI: 10.1007/s00018-005-5054-y

Google Scholar

[4] K. Singpanna, A. Oekchuae, K. Jereonkunmetee, A. Athipornchai, N. Nuntharatanapong, P. Opanasopit, et al., Synthesis and anti-tyrosinase activity evaluation of fluorinated chalcone and phenyl benzyl ether derivatives, Thai Bull Pharm Sci. 15 (2020) 81-89.

Google Scholar

[5] T. Pillaiyar, M. Manickam, V. Namasivayam, Skin whitening agents: medicinal chemistry perspective of tyrosinase inhibitors, J Enzyme Inhib Med Chem. 32 (2017) 403-425.

DOI: 10.1080/14756366.2016.1256882

Google Scholar

[6] D. C. Franco, G. S. de Carvalho, P. R. Rocha, R. da Silva Teixeira, A. D. da Silva, N. R. Raposo, Inhibitory effects of resveratrol analogs on mushroom tyrosinase activity, Molecules. 17 (2012) 11816-11825.

DOI: 10.3390/molecules171011816

Google Scholar

[7] S. J. Bae, Y. M. Ha, Y. J. Park, J. Y. Park, Y. M. Song, T. K. Ha, et al., Design, synthesis, and evaluation of (E)-N-substituted benzylidene-aniline derivatives as tyrosinase inhibitors, Eur J Med Chem. 57 (2012) 383-390.

DOI: 10.1016/j.ejmech.2012.09.026

Google Scholar

[8] A. F. Abdel-Magid, K. G. Carson, B. D. Harris, C. A. Maryanoff, R. D. Shah, Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on direct and indirect reductive amination procedures(1), J Org Chem. 61 (1996) 3849-3862.

DOI: 10.1021/jo960057x

Google Scholar

[9] J. Chompoo, A. Upadhyay, M. Fukuta, S. Tawata, Effect of Alpinia zerumbet components on antioxidant and skin diseases-related enzymes, BMC Complement Altern Med. 12 (2012) 106.

DOI: 10.1186/1472-6882-12-106

Google Scholar

[10] W. Riam-Amatakun, P. Limpachayaporn, J. R. L. Pizon, P. Opanasopit, N. Nuntharatanapon, Anti-melanogenic activity of p-chlorophenyl benzyl ether in α-MSH-induced mouse melanoma B16F10 cells, Key Eng Mater. 819 (2019) 118-123.

DOI: 10.4028/www.scientific.net/kem.819.118

Google Scholar

[11] K. Suttisintong, S. Palakhachane, A. Athipornchai, W. Pimtomg, P. Limpachayaporn, Synthesis and evaluation of anti-tyrosinase activity of phenyl benzyl ether derivatives: Effects of functional groups and their positions, SEHS. 12 (2018) 111-123.

Google Scholar

[12] J.P. Begue, D. Bonnet-Delpon. Bioorganic and medicinal chemistry of fluorine. first ed., John Wiley & Sons, Inc., New Jersey,(2008).

Google Scholar

[13] P. Shah, A. D. Westwell, The role of fluorine in medicinal chemistry, J Enzyme Inhib Med Chem. 22 (2007) 527-540.

Google Scholar