6-(2,5-Dimethoxyphenyl)-2-hydroxycyclohepta-2,4,6-trien-1-one | 1411674-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(2,5-Dimethoxyphenyl)-2-hydroxycyclohepta-2,4,6-trien-1-one
• 英文别名: 6-(2,5-dimethoxyphenyl)-2-hydroxycyclohepta-2,4,6-trien-1-one
• CAS: 1411674-20-8
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: PRPHVLPFKCLRHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 samarium diiodide 、 potassium hydroxide 作用下， 生成 6-(2,5-Dimethoxyphenyl)-2-hydroxycyclohepta-2,4,6-trien-1-one
  参考文献：
  名称：

  Tropolones As Lead-Like Natural Products: The Development of Potent and Selective Histone Deacetylase Inhibitors

  摘要：

  Natural products have long been recognized as a rich source of potent therapeutics but further development is often limited by high structural complexity and high molecular weight. In contrast, at the core of the thujaplicins is a lead-like tropolone scaffold characterized by relatively low molecular weight, ample sites for diversification, and metal-binding functionality poised for targeting a range of metalloenzyme drug targets. Here, we describe the development of this underutilized scaffold for the discovery of tropolone derivatives that function as isozyme-selective inhibitors of the validated anticancer drug target, histone deacetylase (HDAC). Several monosubstituted tropolones display remarkable levels of selectivity for HDAC2 and potently inhibit the growth of T-cell lymphocyte cell lines. The tropolones represent a new chemotype of isozyme-selective HDAC inhibitors.

  DOI：

  10.1021/ml400158k

文献信息

• The furan route to tropolones: probing the antiproliferative effects of β-thujaplicin analogs
  作者：E. Zachary Oblak、Erin S. D. Bolstad、Sophia N. Ononye、Nigel D. Priestley、M. Kyle Hadden、Dennis L. Wright

  DOI：10.1039/c2ob26553b

  日期：——

  A direct route to analogs of the naturally occurring tropolone β-thujaplicin has been developed in just four steps from furan. Using this method, a series of derivatives were synthesized and evaluated. Several of these compounds demonstrated very high levels of potency against bacterial and fungal pathogens with good selectivity over mammalian cells.

  距离天然托洛酮β-thujaplicin类似物的直接途径仅需四个步骤即可完成 呋喃。使用这种方法，合成并评估了一系列衍生物。这些化合物中的几种显示出对细菌和真菌病原体非常高的效力，并且对哺乳动物细胞具有良好的选择性。