3-((Ξ)-2,4-dihydroxy-benzylidene)-chroman-2,4-dione | 30113-71-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: 3-((Ξ)-2,4-dihydroxy-benzylidene)-chroman-2,4-dione
• 英文别名: 3-((Ξ)-2,4-Dihydroxy-benzyliden)-chroman-2,4-dion；3-[(2,4-Dihydroxy phenyl)methylidene]-2h-chromene-2,4-dione；3-[(2,4-dihydroxyphenyl)methylidene]chromene-2,4-dione
• CAS: 30113-71-4
• 化学式: C₁₆H₁₀O₅
• 分子量: 282.252
• InChiKey: KPUQDDJACDGWIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2H-1-苯并吡喃-2,4(3H)-二酮 、 2,4-二羟基苯甲醛 在 乙醇 作用下， 生成 3-((Ξ)-2,4-dihydroxy-benzylidene)-chroman-2,4-dione
  参考文献：
  名称：

  Studies on 4-Hydroxycoumarins. II. The Condensation of Aldehydes with 4-Hydroxycoumarins¹

  摘要：

  DOI：

  10.1021/ja01252a008

文献信息

• Structure-based design, synthesis and biological evaluation of β-glucuronidase inhibitors
  作者：Khalid M. Khan、Nida Ambreen、Muhammad Taha、Sobia A. Halim、Zaheer-ul-Haq、Shagufta Naureen、Saima Rasheed、Shahnaz Perveen、Sajjad Ali、Mohammad Iqbal Choudhary

  DOI：10.1007/s10822-014-9745-z

  日期：2014.5

  Using structure-based virtual screening approach, a coumarin derivative (1) was identified as β-glucuronidase inhibitor. A focused library of coumarin derivatives was synthesized by eco-benign version of chemical reaction, and all synthetic compounds were characterized by using spectroscopy. These compounds were found to be inhibitor of β-glucuronidase with IC50 values in a micromolar range. All synthetic compounds exhibited interesting inhibitory activity against β-glucuronidase, however, their potency varied substantially from IC50 = 9.9–352.6 µM. Of twenty-one compounds, four exhibited a better inhibitory profile than the initial hit 1. Interestingly, compounds 1e, 1k, 1n and 1p exhibited more potency than the standard inhibitor with IC50 values 34.2, 21.4, 11.7, and 9.9 µM, respectively. We further studied their dose responses and also checked our results by using detergent Triton ×-100. We found that our results are true and not affected by detergent.

  利用基于结构的虚拟筛选方法，发现了一种香豆素衍生物（1）作为β-葡萄糖苷酸酶抑制剂。通过环保型化学反应合成了一个香豆素衍生物的重点库，并通过光谱技术对所有合成化合物进行了表征。这些化合物被发现是β-葡萄糖苷酸酶的抑制剂，其IC50值在微摩尔范围内。所有合成化合物对β-葡萄糖苷酸酶表现出有趣的抑制活性，但其效力差异显著，IC50值从9.9至352.6微摩尔不等。在二十一种化合物中，有四种表现出比初始命中物1更好的抑制性能。有趣的是，化合物1e、1k、1n和1p的效力超过了标准抑制剂，其IC50值分别为34.2、21.4、11.7和9.9微摩尔。我们进一步研究了它们的剂量反应，并通过使用洗涤剂Triton ×-100验证了我们的结果。我们发现我们的结果是真实的，并且不受洗涤剂的影响。
• Studies on 4-Hydroxycoumarins. II. The Condensation of Aldehydes with 4-Hydroxycoumarins¹
  作者：William R. Sullivan、Charles F. Huebner、Mark A. Stahmann、Karl Paul Link

  DOI：10.1021/ja01252a008

  日期：1943.12