Tyrosinase Inhibitory Effects of Derivatives of (E)‐2‐(Substituted Benzylidene)‐3,4‐Dihydronaphthalen‐1(2H)‐One,Bulletin of the Korean Chemical Society

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Tyrosinase Inhibitory Effects of Derivatives of (E)‐2‐(Substituted Benzylidene)‐3,4‐Dihydronaphthalen‐1(2H)‐One
Bulletin of the Korean Chemical Society ( IF 2.3 ) Pub Date : 2020-10-08 , DOI: 10.1002/bkcs.12122
Il Young Ryu ₁ , Inkyu Choi ₁ , Sultan Ullah ₁ , Heejeong Choi ₁ , Pusoon Chun ₂ , Hyung Ryong Moon ₁

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Tyrosinase plays an essential role in melanin biosynthesis, and as such it has received great attention as a key target for the treatment of pigmentation disorders. In our earlier studies, we explored analogs with the β‐phenyl‐α,β‐unsaturated carbonyl template, and the results obtained indicated that this template confers potent tyrosinase inhibitory activity. Thus, in the present study, (E)‐2‐(substituted benzylidene)‐3,4‐dihydronaphthalen‐1(2H)‐one derivatives (compounds 1–6) with this template were synthesized and investigated with respect to their mushroom tyrosinase inhibitory effects. Derivative 4 with a 3‐hydroxy‐4‐methoxyl substituent on the β–phenyl ring of the template inhibited mushroom tyrosinase fourfold more than kojic acid (IC₅₀ = 15.60 ± 0.32 μM vs. 57.06 ± 0.46 μM). In silico docking simulation supported this potent inhibitory activity of compound 4 by demonstrating a binding energy of −6.4 kcal/mol at the active site of mushroom tyrosinase. Kinetic results imply that 4 competitively inhibits mushroom tyrosinase.

中文翻译：

（E）-2-（取代的亚苄基）-3,4-二氢萘-1（2H）-1衍生物的酪氨酸酶抑制作用

酪氨酸酶在黑色素的生物合成中起着至关重要的作用，因此作为色素沉着症治疗的主要靶点，酪氨酸酶受到了极大的关注。在我们的早期研究中，我们探索了具有β-苯基-α，β-不饱和羰基模板的类似物，并且获得的结果表明该模板具有强大的酪氨酸酶抑制活性。因此，在本研究中，（ë）-2-（取代亚苄基）-3,4-二氢萘-1（2 ħ） -酮衍生物（化合物1 - 6）与该模板合成和相对于研究它们的蘑菇酪氨酸酶抑制作用。导数4在模板的β-苯环上带有3-羟基-4-甲氧基取代基的蘑菇状酪氨酸酶抑制率比曲酸高出四倍（IC ₅₀ = 15.60±0.32μMvs. 57.06±0.46μM）。在计算机对接模拟中，通过证明蘑菇酪氨酸酶活性位点处的结合能为-6.4 kcal / mol，从而支持了化合物4的这种强抑制活性。动力学结果表明4竞争性抑制蘑菇酪氨酸酶。

更新日期：2020-10-08

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