3-bromo-5-hydroxy-4,6-dimethoxyphthalide | 104189-61-9

• 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: 3-bromo-5-hydroxy-4,6-dimethoxyphthalide
• 英文别名: 3-bromo-5-hydroxy-4,6-dimethoxy-3H-isobenzofuran-1-one；3-Bromo-5-hydroxy-4,6-dimethoxyphthalide；3-bromo-5-hydroxy-4,6-dimethoxy-3H-2-benzofuran-1-one
• CAS: 104189-61-9
• 化学式: C₁₀H₉BrO₅
• 分子量: 289.082
• InChiKey: YEJMLKGYZMQBBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-bromo-5-hydroxy-4,6-dimethoxyphthalide 在 水 作用下， 反应 1.0h， 生成 3,5-dihydroxy-4,6-dimethoxy-3H-isobenzofuran-1-one
  参考文献：
  名称：

  Rational design of inhibitors of VirA–VirG two-component signal transduction

  摘要：

  VirA-VirG two-component system regulates the vir (virulence) operon in response to specific host factors (xenognosins) in the plant pathogen Agrobacterium tumefaciens. Using whole cell assays, stable inhibitors inspired by the labile natural benzoxazinone inhibitor HDMBOA are developed. It is found that aromatic aldehydes represent a minimal structural unit for activity. In particular, 3-hydroxy-4,6-dimethoxy-3H-isobenzofuran-1-one (HDI) was found to have the highest activity, making it the most potent developed inhibitor of virulence gene expression in Agrobacterium. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.018
• 作为产物：
  描述：

  5-hydroxy-4,6-dimethoxy-3H-isobenzofuran-1-one 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 0.5h， 以80%的产率得到3-bromo-5-hydroxy-4,6-dimethoxyphthalide
  参考文献：
  名称：

  Rational design of inhibitors of VirA–VirG two-component signal transduction

  摘要：

  VirA-VirG two-component system regulates the vir (virulence) operon in response to specific host factors (xenognosins) in the plant pathogen Agrobacterium tumefaciens. Using whole cell assays, stable inhibitors inspired by the labile natural benzoxazinone inhibitor HDMBOA are developed. It is found that aromatic aldehydes represent a minimal structural unit for activity. In particular, 3-hydroxy-4,6-dimethoxy-3H-isobenzofuran-1-one (HDI) was found to have the highest activity, making it the most potent developed inhibitor of virulence gene expression in Agrobacterium. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.018

文献信息

• Analogs of pyrimidine nucleosides. 19. Synthesis, antineoplastic activity, and kinetics of the hydrolysis of 1-(3-phthalidyl)-5-fluorouracils
  作者：R. A. Zhuk、A. S. Ludzisha、E. G. Shpaer、M. Yu. Lidak、A. A. Zidermane、D. V. Meirena

  DOI：10.1007/bf00515261

  日期：1985.10
• Rational design of inhibitors of VirA–VirG two-component signal transduction
  作者：Justin Maresh、Jin Zhang、Yih-Ling Tzeng、Nora A. Goodman、David G. Lynn

  DOI：10.1016/j.bmcl.2007.04.018

  日期：2007.6

  VirA-VirG two-component system regulates the vir (virulence) operon in response to specific host factors (xenognosins) in the plant pathogen Agrobacterium tumefaciens. Using whole cell assays, stable inhibitors inspired by the labile natural benzoxazinone inhibitor HDMBOA are developed. It is found that aromatic aldehydes represent a minimal structural unit for activity. In particular, 3-hydroxy-4,6-dimethoxy-3H-isobenzofuran-1-one (HDI) was found to have the highest activity, making it the most potent developed inhibitor of virulence gene expression in Agrobacterium. (c) 2007 Elsevier Ltd. All rights reserved.