1-(1-(4-hydroxyphenyl)butan-2-ylidene)thiosemicarbazide | 339246-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-(1-(4-hydroxyphenyl)butan-2-ylidene)thiosemicarbazide
• 英文别名: 1-(4-(4-hydroxyphenyl)butan-2-ylidene)thiosemicarbazide；4-(4-hydroxyphenyl)butan-2-ylidenethiosemicarbazide；N'-[4-(4-hydroxyphenyl)butan-2-ylideneamino]carbamimidothioic acid
• CAS: 339246-36-5
• 化学式: C₁₁H₁₅N₃OS
• 分子量: 237.326
• InChiKey: MOEKCSYKLBVRDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  氨基硫脲 、 覆盆子酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以71%的产率得到1-(1-(4-hydroxyphenyl)butan-2-ylidene)thiosemicarbazide
  参考文献：
  名称：

  1-（1-芳基亚乙基）硫代氨基脲衍生物：一类新型的酪氨酸酶抑制剂。

  摘要：

  合成了一系列的1-（1-芳基亚乙基）硫代氨基脲化合物及其类似物，并通过1 H NMR，MS进行了表征。通过与4-甲氧基肉桂酸和熊果苷相比，基于酪氨酸酶对L-DOPA的氧化的催化能力的测定，研究了它们的酪氨酸酶抑制活性。结果表明：（1）所有合成的化合物均对酪氨酸酶具有明显的抑制作用；（2）对于这些化合物，与酪氨酸酶中心相互作用的主要活性部分是硫代氨基脲基。（3）抑制活性与硫代氨基脲部分和连接在芳环上的基团密切相关。

  DOI：

  10.1016/j.bmc.2007.10.102

文献信息

• 1-(1-Arylethylidene)thiosemicarbazide derivatives: A new class of tyrosinase inhibitors
  作者：Jinbing Liu、Wei Yi、Yiqian Wan、Lin Ma、Huacan Song

  DOI：10.1016/j.bmc.2007.10.102

  日期：2008.2.1

  A series of 1-(1-arylethylidene)thiosemicarbazide compounds and their analogues were synthesized and characterized by 1H NMR, MS. Their tyrosinase inhibitory activities were investigated by an assay based on the catalyzing ability of tyrosinase for the oxidation of L-DOPA, comparing with 4-methoxycinnamic acid and arbutin. The results showed that (1) all the synthesized compounds could perform a significant

  合成了一系列的1-（1-芳基亚乙基）硫代氨基脲化合物及其类似物，并通过1 H NMR，MS进行了表征。通过与4-甲氧基肉桂酸和熊果苷相比，基于酪氨酸酶对L-DOPA的氧化的催化能力的测定，研究了它们的酪氨酸酶抑制活性。结果表明：（1）所有合成的化合物均对酪氨酸酶具有明显的抑制作用；（2）对于这些化合物，与酪氨酸酶中心相互作用的主要活性部分是硫代氨基脲基。（3）抑制活性与硫代氨基脲部分和连接在芳环上的基团密切相关。
• A class of potent tyrosinase inhibitors: Alkylidenethiosemicarbazide compounds
  作者：Jinbing Liu、Rihui Cao、Wei Yi、Chunming Ma、Yiqian Wan、Binhua Zhou、Lin Ma、Huacan Song

  DOI：10.1016/j.ejmech.2008.04.002

  日期：2009.4

  A series of alkylidenethiosemicarbazide compounds were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that most of the synthesized compounds exhibited significant inhibitory activities. Especially, compound 1f was found to be the most potent inhibitor with IC50 value of 0.086 mu M, suggesting that further development of such compounds may be of interest. (c) 2008 Elsevier Masson SAS. All rights reserved.
• Rational design, synthesis and structure–activity relationships of 4-alkoxy- and 4-acyloxy-phenylethylenethiosemicarbazone analogues as novel tyrosinase inhibitors
  作者：Ao You、Jie Zhou、Senchuan Song、Guoxun Zhu、Huacan Song、Wei Yi

  DOI：10.1016/j.bmc.2015.01.024

  日期：2015.3

  In continuing our program aimed to search for potent compounds as highly efficient tyrosinase inhibitors, here a series of novel 4-alkoxy- and 4-acyloxy-phenylethylenethiosemicarbazone analogues were designed, synthesized and their biological activities on mushroom tyrosinase were evaluated. Notably, most of compounds displayed remarkable tyrosinase inhibitory activities with IC50 value of lower than 1.0 mu M. Furthermore, the structure-activity relationships (SARs) were discussed and the inhibition mechanism and the inhibitory kinetics of selected compounds 7k and 8d were also investigated. Taken together, these results suggested that such compounds could serve as the promising candidates for the treatment of tyrosinase-related disorders and further development of such compounds might be of great interest. (C) 2015 Published by Elsevier Ltd.