methyl 4-(2-(2-(2-(2-(prop-2-ynyloxy)-ethoxy)-ethoxy)-ethoxy)-ethoxy)benzoate | 1372163-85-3

• 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: methyl 4-(2-(2-(2-(2-(prop-2-ynyloxy)-ethoxy)-ethoxy)-ethoxy)-ethoxy)benzoate
• CAS: 1372163-85-3
• 化学式: C₁₉H₂₆O₇
• 分子量: 366.411
• InChiKey: LNXOHYZHXGKZGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  26.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 4-(2-(2-(2-(2-(prop-2-ynyloxy)-ethoxy)-ethoxy)-ethoxy)-ethoxy)benzoate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以72%的产率得到4-(2-{2-[2-(2-prop-2-ynyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzoic acid hydrazide
  参考文献：
  名称：

  Design, Synthesis, and Initial Biological Evaluation of a Steroidal Anti-Estrogen–Doxorubicin Bioconjugate for Targeting Estrogen Receptor-Positive Breast Cancer Cells

  摘要：

  As part of our program to develop breast cancer specific therapeutic agents, we have synthesized a conjugate agent that is a conjugate of the steroidal anti-estrogen and the potent cytotoxin doxorubicin. In this effort, we employed a modular assembly approach to prepare a novel 11 beta-substituted steroidal anti-estrogen functionalized with an azido-tetraethylene glycol moiety, which could be coupled to a complementary doxorubicin benzoyl hydrazone functionalized with a propargyl tetraethylene glycol moiety. Huisgen [3 + 2] cycloaddition chemistry gave the final hybrid that was evaluated for selective uptake and cytotoxicity in ER(+)-MCF-7 and ER(-)-MDA-MB-231 breast cancer cell lines. The results demonstrated that the presence of the anti-estrogenic component in the hybrid compound was critical for selectivity and cytotoxicity in ER(+)-MCF-7 human breast cancer cells as the hybrid was similar to 70-fold more potent than doxorubicin in inhibition of cell proliferation and promoting cell death.

  DOI：

  10.1021/bc200645n
• 作为产物：
  描述：

  三缩四乙二醇 在 sodium hydride 、 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 paraffin oil 为溶剂， 反应 56.5h， 生成 methyl 4-(2-(2-(2-(2-(prop-2-ynyloxy)-ethoxy)-ethoxy)-ethoxy)-ethoxy)benzoate
  参考文献：
  名称：

  Design, Synthesis, and Initial Biological Evaluation of a Steroidal Anti-Estrogen–Doxorubicin Bioconjugate for Targeting Estrogen Receptor-Positive Breast Cancer Cells

  摘要：

  As part of our program to develop breast cancer specific therapeutic agents, we have synthesized a conjugate agent that is a conjugate of the steroidal anti-estrogen and the potent cytotoxin doxorubicin. In this effort, we employed a modular assembly approach to prepare a novel 11 beta-substituted steroidal anti-estrogen functionalized with an azido-tetraethylene glycol moiety, which could be coupled to a complementary doxorubicin benzoyl hydrazone functionalized with a propargyl tetraethylene glycol moiety. Huisgen [3 + 2] cycloaddition chemistry gave the final hybrid that was evaluated for selective uptake and cytotoxicity in ER(+)-MCF-7 and ER(-)-MDA-MB-231 breast cancer cell lines. The results demonstrated that the presence of the anti-estrogenic component in the hybrid compound was critical for selectivity and cytotoxicity in ER(+)-MCF-7 human breast cancer cells as the hybrid was similar to 70-fold more potent than doxorubicin in inhibition of cell proliferation and promoting cell death.

  DOI：

  10.1021/bc200645n