2'-O-[2-(2-(6-azidohexyloxy)-2-oxoethoxy)acetyl]-7-O-alloc-paclitaxel | 1246194-67-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2'-O-[2-(2-(6-azidohexyloxy)-2-oxoethoxy)acetyl]-7-O-alloc-paclitaxel
• CAS: 1246194-67-1
• 化学式: C₆₁H₇₀N₄O₂₀
• 分子量: 1179.24
• InChiKey: IPYTXOCNUXQPOF-MQPDBWHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.06
• 重原子数：
  85.0
• 可旋转键数：
  25.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  326.95
• 氢给体数：
  2.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  2'-O-[2-(2-(6-azidohexyloxy)-2-oxoethoxy)acetyl]-7-O-alloc-paclitaxel 在 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以72%的产率得到2'-[2-(2-(6-azidohexyloxy)-2-oxoethoxy)acetyl]-O-paclitaxel
  参考文献：
  名称：

  Novel Targeted System To Deliver Chemotherapeutic Drugs to EphA2-Expressing Cancer Cells

  摘要：

  The efficacy of anticancer drugs is often limited by their systemic toxicities and adverse side effects. We report that the EphA2 receptor is overexpressed preferentially in several human cancer cell lines compared to normal tissues and that an EphA2 targeting peptide (YSAYPDSVPMMS) can be effective in delivering anticancer agents to such tumors. Hence, we report on the synthesis and characterizations of a novel EphA2-targeting agent conjugated with the chemotherapeutic drug paclitaxel. We found that the peptide-drug conjugate is dramatically more effective than paclitaxel alone at inhibiting tumor growth in a prostate cancer xenograft model, delivering significantly higher levels of drug to the tumor site. We believe these studies open the way to the development of a new class of therapeutic compounds that exploit the EphA2 receptor for drug delivery to cancer cells.

  DOI：

  10.1021/jm201743s
• 作为产物：
  描述：

  2'-O-TBS-7-O-alloc-paclitaxel 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 2'-O-[2-(2-(6-azidohexyloxy)-2-oxoethoxy)acetyl]-7-O-alloc-paclitaxel
  参考文献：
  名称：

  Novel Targeted System To Deliver Chemotherapeutic Drugs to EphA2-Expressing Cancer Cells

  摘要：

  The efficacy of anticancer drugs is often limited by their systemic toxicities and adverse side effects. We report that the EphA2 receptor is overexpressed preferentially in several human cancer cell lines compared to normal tissues and that an EphA2 targeting peptide (YSAYPDSVPMMS) can be effective in delivering anticancer agents to such tumors. Hence, we report on the synthesis and characterizations of a novel EphA2-targeting agent conjugated with the chemotherapeutic drug paclitaxel. We found that the peptide-drug conjugate is dramatically more effective than paclitaxel alone at inhibiting tumor growth in a prostate cancer xenograft model, delivering significantly higher levels of drug to the tumor site. We believe these studies open the way to the development of a new class of therapeutic compounds that exploit the EphA2 receptor for drug delivery to cancer cells.

  DOI：

  10.1021/jm201743s