5-isopropyl-2,3,4-trimethoxybenzaldehyde | 1011708-94-3

• 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: 5-isopropyl-2,3,4-trimethoxybenzaldehyde
• 英文别名: 2,3,4-Trimethoxy-5-propan-2-ylbenzaldehyde
• CAS: 1011708-94-3
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: WFFYVRZAOLYMAK-UHFFFAOYSA-N

物化性质

• 沸点：
  359.7±42.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-isopropyl-2,3,4-trimethoxybenzaldehyde 在 咪唑 、 4-二甲氨基吡啶 、 叔丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 正戊烷 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Synthesis of new mixed phenol/heterocyclic derivatives and studies of their activity as inhibitors of Bax/Bcl-xL interaction

  摘要：

  We describe here the synthesis of a series of new molecules containing phenol and heteroaromatic moieties, compounds, which have been evaluated for their ability to inhibit Bax/Bcl-xL interactions in BRET assays. Among them, a triazole derivative 13, exhibit a very promising activity, being more potent than the reference compounds acylpyrogallol 1 and ABT 737. These preliminary results demonstrate that derivatives of this family can be attractive to develop new molecules with potent anticancer activity. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.060
• 作为产物：
  描述：

  1-isopropyl-2,3,4-trimethoxybenzene 、 N,N-二甲基甲酰胺 以 四氢呋喃 、 六甲基磷酰三胺 、 正戊烷 为溶剂， 反应 4.5h， 以91%的产率得到5-isopropyl-2,3,4-trimethoxybenzaldehyde
  参考文献：
  名称：

  Acylpyrogallols as Inhibitors of Antiapoptotic Bcl-2 Proteins

  摘要：

  A series of acylpyrogallols were designed, synthesized, and evaluated as small-molecule inhibitors of antiapoptotic Bcl-2 proteins. The most potent compound 9 (TM-179) binds to Bcl-2 with an IC50 of 170 nM and to Mcl-1 with a K-i of 37 nM. Compound 9 potently inhibits cell growth and induces apoptosis in human breast and prostate cancer cell lines.

  DOI：

  10.1021/jm701358v

文献信息

• Synthesis of new mixed phenol/heterocyclic derivatives and studies of their activity as inhibitors of Bax/Bcl-xL interaction
  作者：Duc Duy Vo、Fabien Gautier、Sophie Barillé-Nion、Philippe Juin、Nicolas Levoin、René Grée

  DOI：10.1016/j.tet.2013.11.060

  日期：2014.1

  We describe here the synthesis of a series of new molecules containing phenol and heteroaromatic moieties, compounds, which have been evaluated for their ability to inhibit Bax/Bcl-xL interactions in BRET assays. Among them, a triazole derivative 13, exhibit a very promising activity, being more potent than the reference compounds acylpyrogallol 1 and ABT 737. These preliminary results demonstrate that derivatives of this family can be attractive to develop new molecules with potent anticancer activity. (c) 2013 Elsevier Ltd. All rights reserved.
• Acylpyrogallols as Inhibitors of Antiapoptotic Bcl-2 Proteins
  作者：Guozhi Tang、Zaneta Nikolovska-Coleska、Su Qiu、Chao-Yie Yang、Jie Guo、Shaomeng Wang

  DOI：10.1021/jm701358v

  日期：2008.2.1

  A series of acylpyrogallols were designed, synthesized, and evaluated as small-molecule inhibitors of antiapoptotic Bcl-2 proteins. The most potent compound 9 (TM-179) binds to Bcl-2 with an IC50 of 170 nM and to Mcl-1 with a K-i of 37 nM. Compound 9 potently inhibits cell growth and induces apoptosis in human breast and prostate cancer cell lines.