methyl 5-({[[4-(benzyloxy)phenyl](methyl)amino]carbonyl}oxy)-2-hydroxybenzoate

• 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: methyl 5-({[[4-(benzyloxy)phenyl](methyl)amino]carbonyl}oxy)-2-hydroxybenzoate
• 英文别名: Methyl 2-hydroxy-5-[methyl-(4-phenylmethoxyphenyl)carbamoyl]oxybenzoate；methyl 2-hydroxy-5-[methyl-(4-phenylmethoxyphenyl)carbamoyl]oxybenzoate
• 化学式: C₂₃H₂₁NO₆
• 分子量: 407.423
• InChiKey: AGHGBOMBRSVLJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-({[[4-(benzyloxy)phenyl](methyl)amino]carbonyl}oxy)-2-hydroxybenzoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、393.01 kPa 条件下， 反应 5.0h， 以100%的产率得到methyl 2-hydroxy-5-({[(4-hydroxyphenyl)-(methyl)amino]carbonyl}oxy)benzoate
  参考文献：
  名称：

  New Inhibitors of Angiogenesis with Antitumor Activity in Vivo

  摘要：

  Angiogenesis is a requirement for the sustained growth and proliferation of solid tumors, and the development of new compounds that induce a sustained inhibition of the proangiogenic signaling generated by tumor hypoxia still remains as an important unmet need. In this work, we describe a new antiangiogenic compound (22) that inhibits proangiogenic signaling under hypoxic conditions in breast cancer cells. Compound 22 blocks the MAPK pathway, impairs cellular migration under hypoxic conditions, and regulates a set of genes related to angiogenesis. These responses are mediated by HIF-1 alpha, since the effects of compound 22 mostly disappear when its expression is knocked-down. Furthermore, administration of compound 22 in a xenograft model of breast cancer produced tumor growth reductions ranging from 46 to 55% in 38% of the treated animals without causing any toxic side effects. Importantly, in the responding tumors, a significant reduction in the number of blood vessels was observed, further supporting the mechanism of action of the compound. These findings provide a rationale for the development of new antiangiogenic compounds that could eventually lead to new drugs suitable for the treatment of some types of tumors either alone or in combination with other agents.

  DOI：

  10.1021/jm5019252
• 作为产物：
  描述：

  4-苄氧基-N-甲基苯胺 在 碘甲烷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 58.0h， 生成 methyl 5-({[[4-(benzyloxy)phenyl](methyl)amino]carbonyl}oxy)-2-hydroxybenzoate
  参考文献：
  名称：

  New Inhibitors of Angiogenesis with Antitumor Activity in Vivo

  摘要：

  Angiogenesis is a requirement for the sustained growth and proliferation of solid tumors, and the development of new compounds that induce a sustained inhibition of the proangiogenic signaling generated by tumor hypoxia still remains as an important unmet need. In this work, we describe a new antiangiogenic compound (22) that inhibits proangiogenic signaling under hypoxic conditions in breast cancer cells. Compound 22 blocks the MAPK pathway, impairs cellular migration under hypoxic conditions, and regulates a set of genes related to angiogenesis. These responses are mediated by HIF-1 alpha, since the effects of compound 22 mostly disappear when its expression is knocked-down. Furthermore, administration of compound 22 in a xenograft model of breast cancer produced tumor growth reductions ranging from 46 to 55% in 38% of the treated animals without causing any toxic side effects. Importantly, in the responding tumors, a significant reduction in the number of blood vessels was observed, further supporting the mechanism of action of the compound. These findings provide a rationale for the development of new antiangiogenic compounds that could eventually lead to new drugs suitable for the treatment of some types of tumors either alone or in combination with other agents.

  DOI：

  10.1021/jm5019252