2',4'-dihydroxy-3-methoxy-α,β-dihydrochalcone | 851192-44-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2',4'-dihydroxy-3-methoxy-α,β-dihydrochalcone
• 英文别名: 1-(2,4-dihydroxyphenyl)-3-(3-methoxyphenyl)propan-1-one；1-(2,4-Dihydroxyphenyl)-3-(3-methoxyphenyl)propan-1-one
• CAS: 851192-44-4
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: GIQXQTKQHGIYJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-1-(2,4-dihydroxyphenyl)-3-(3-methoxyphenyl)prop-2-en-1-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以98%的产率得到2',4'-dihydroxy-3-methoxy-α,β-dihydrochalcone
  参考文献：
  名称：

  2′,4′-Dihydroxy-3-methoxy-α,β-dihydrochalcone and 2′,4-dihydroxy-α,β-dihydrochalcone: supramolecular structures formed by O—H...O, C—H...O and stacking interactions

  摘要：

  The crystal structures of 2',4'- dihydroxy- 3- methoxy-alpha,beta-dihydrochalcone, C16H16O4, and 2',4- dihydroxy-alpha,beta- dihydrochalcone, C15H14O3, have been determined. In both compounds, the structure consists of two nearly planar six-membered aromatic rings connected by a propanal chain, which is bent in the methoxy compound and almost straight in the other compound. In the crystal structures, the molecular units of both compounds are linked by O - H center dot center dot center dot O hydrogen bonds to form infinite one- dimensional chains. Hydrogen bonds and C - H center dot center dot center dot O contacts in the crystal structures were studied by topological analysis of charge density based on Hartree - Fock calculations. Almost all of the investigated C - H center dot center dot center dot O contacts should be characterized as weak hydrogen bonds.

  DOI：

  10.1107/s0108270105013661

文献信息

• Design, Synthesis, and Biological Evaluation of Novel Hybrids Containing Dihydrochalcone as Tyrosinase Inhibitors to Treat Skin Hyperpigmentation
  作者：Songtao Xue、Zhiwei Li、Xiaotong Ze、Xiuyuan Wu、Chen He、Wen Shuai、Maria Marlow、Jian Chen、David Scurr、Zheying Zhu、Jinyi Xu、Shengtao Xu

  DOI：10.1021/acs.jmedchem.3c00012

  日期：——

  deposition may lead to a series of skin disorders. The production of melanin is carried out by melanocytes, in which the enzyme tyrosinase performs a key role. In this work, we identified a series of novel tyrosinase inhibitor hybrids with a dihydrochalcone skeleton and resorcinol structure, which can inhibit tyrosinase activity and reduce the melanin content in the skin. Compound 11c possessed the most

  黑色素沉积过多可能会导致一系列的皮肤病。黑色素的产生是由黑色素细胞进行的，其中酪氨酸酶起着关键作用。在这项工作中，我们鉴定了一系列具有二氢查耳酮骨架和间苯二酚结构的新型酪氨酸酶抑制剂杂化物，它们可以抑制酪氨酸酶活性并减少皮肤中的黑色素含量。化合物11c具有最强的抗酪氨酸酶活性，在纳摩尔浓度范围内显示出 IC 50值，同时具有显着的抗氧化活性和低细胞毒性。此外，在 HPLC 分析和 3D OrbiSIMS 成像可视化支持下的体外渗透测试表明11c具有出色的渗透性. 更重要的是，化合物11c在体内的豚鼠模型中减少了紫外线诱导的皮肤色素沉着中的黑色素含量。这些结果表明，化合物11c可以作为一种很有前途的强效酪氨酸酶抑制剂，用于开发治疗皮肤色素沉着过度的潜在疗法。