1,5-bis((1-(2-(pyrrolidin-1-yl)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)anthracene-9,10-dione | 1100335-75-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,5-bis((1-(2-(pyrrolidin-1-yl)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)anthracene-9,10-dione
• CAS: 1100335-75-8
• 化学式: C₃₂H₃₆N₈O₄
• 分子量: 596.689
• InChiKey: YBLSJXKEWQKGRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  44.0
• 可旋转键数：
  12.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  120.5
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1,5-bis((1-(2-(pyrrolidin-1-yl)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)anthracene-9,10-dione 、 碘甲烷 以 氯仿 为溶剂， 反应 16.0h， 以94%的产率得到1,1'-(2,2'-(4,4'-(9,10-dioxo-9,10-dihydroanthracene-1,5-diyl)bis(oxy)bis(methylene)bis(1H-1,2,3-triazole-4,1-diyl))bis(ethane-2,1-diyl))bis(1-methylpyrrolidinium) iodide
  参考文献：
  名称：

  Novel anthraquinone derivatives: Synthesis via click chemistry approach and their induction of apoptosis in BGC gastric cancer cells via reactive oxygen species(ROS)-dependent mitochondrial pathway

  摘要：

  Three water soluble anthraquinone derivatives were designed and synthesized employing click chemistry to prepare novel and potent antitumor drugs. An MTT assay indicated that all compounds had significant inhibitory activity against BGC gastric cancer cells in vitro. Apoptosis induced by these compounds was observed by flow cytometry and laser confocal microscopy. Mechanistic analysis showed that these compounds induced the generation of several reactive oxygen species, the loss of mitochondrial membrane potential (Delta psi m), the transition of mitochondrial permeability, and the release of cytochrome C from the mitochondrion to cytoplasm. These results suggest that the anthraquinones might be potential lead compounds for the cancer chemotherapy. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.047
• 作为产物：
  描述：

  1,5-bis(prop-2'-ynyloxy)anthraquinone 、 1-(2-叠氮乙基)吡咯烷 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 以72%的产率得到1,5-bis((1-(2-(pyrrolidin-1-yl)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)anthracene-9,10-dione
  参考文献：
  名称：

  Novel anthraquinone derivatives: Synthesis via click chemistry approach and their induction of apoptosis in BGC gastric cancer cells via reactive oxygen species(ROS)-dependent mitochondrial pathway

  摘要：

  Three water soluble anthraquinone derivatives were designed and synthesized employing click chemistry to prepare novel and potent antitumor drugs. An MTT assay indicated that all compounds had significant inhibitory activity against BGC gastric cancer cells in vitro. Apoptosis induced by these compounds was observed by flow cytometry and laser confocal microscopy. Mechanistic analysis showed that these compounds induced the generation of several reactive oxygen species, the loss of mitochondrial membrane potential (Delta psi m), the transition of mitochondrial permeability, and the release of cytochrome C from the mitochondrion to cytoplasm. These results suggest that the anthraquinones might be potential lead compounds for the cancer chemotherapy. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.047