2-[N-(2-chloroethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilino]ethyl methanesulfonate | 1422986-49-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-[N-(2-chloroethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilino]ethyl methanesulfonate
• CAS: 1422986-49-9
• 化学式: C₁₇H₂₇BClNO₅S
• 分子量: 403.735
• InChiKey: QHVMNROWPFFMRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[N-(2-chloroethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilino]ethyl methanesulfonate 在 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以90%的产率得到N-(2-bromoethyl)-N-(2-chloroethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
  参考文献：
  名称：

  ANTI-CANCER AGENTS

  摘要：

  本文描述了一些化合物，这些化合物可以被选择性地激活，以在肿瘤细胞中产生活性抗癌剂。还公开了包括这些化合物的药物组合物，以及使用这些化合物治疗癌症的方法。

  公开号：

  US20130045949A1
• 作为产物：
  描述：

  2-[(4-bromo-phenyl)-(2-hydroxy-ethyl)-amino]-ethanol 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 三乙胺 、 lithium chloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙腈 为溶剂， 反应 18.5h， 生成 2-[N-(2-chloroethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilino]ethyl methanesulfonate
  参考文献：
  名称：

  Reactive Oxygen Species (ROS) Inducible DNA Cross-Linking Agents and Their Effect on Cancer Cells and Normal Lymphocytes

  摘要：

  Reducing host toxicity is one of the main challenges of cancer chemotherapy. Many tumor cells contain high levels of ROS that make them distinctively different from normal cells. We report a series of ROS-activated aromatic nitrogen mustards that selectively kill chronic lymphocytic leukemia (CLL) over normal lymphocytes. These agents showed powerful DNA cross-linking abilities when coupled with H2O2, one of the most common ROS in cancer cells, whereas little DNA cross-linking was detected without H2O2. Consistent with chemistry observation, in vitro cytotoxicity assay demonstrated that these agents induced 40-80% apoptosis in primary leukemic lymphocytes isolated from CLL patients but less than 25% cell death to normal lymphocytes from healthy donors. The IC50 for the most potent compound (2) was similar to 5 mu M in CLL cells, while the IC50 was not achieved in normal lymphocytes. Collectively, these data provide utility and selectivity of these agents that will inspire further and effective applications.

  DOI：

  10.1021/jm401349g

文献信息

• ANTI-CANCER AGENTS
  申请人：Peng Xiaohua

  公开号：US20130045949A1

  公开（公告）日：2013-02-21

  Described herein are compounds that may be selectively activated to produce active anti-cancer agents in tumor cells. Also disclosed are pharmaceutical compositions comprising the compounds, and methods of treating cancer using the compounds.

  本文描述了一些化合物，这些化合物可以被选择性地激活，以在肿瘤细胞中产生活性抗癌剂。还公开了包括这些化合物的药物组合物，以及使用这些化合物治疗癌症的方法。
• Reactive Oxygen Species (ROS) Inducible DNA Cross-Linking Agents and Their Effect on Cancer Cells and Normal Lymphocytes
  作者：Wenbing Chen、Kumudha Balakrishnan、Yunyan Kuang、Yanyan Han、Min Fu、Varsha Gandhi、Xiaohua Peng

  DOI：10.1021/jm401349g

  日期：2014.6.12

  Reducing host toxicity is one of the main challenges of cancer chemotherapy. Many tumor cells contain high levels of ROS that make them distinctively different from normal cells. We report a series of ROS-activated aromatic nitrogen mustards that selectively kill chronic lymphocytic leukemia (CLL) over normal lymphocytes. These agents showed powerful DNA cross-linking abilities when coupled with H2O2, one of the most common ROS in cancer cells, whereas little DNA cross-linking was detected without H2O2. Consistent with chemistry observation, in vitro cytotoxicity assay demonstrated that these agents induced 40-80% apoptosis in primary leukemic lymphocytes isolated from CLL patients but less than 25% cell death to normal lymphocytes from healthy donors. The IC50 for the most potent compound (2) was similar to 5 mu M in CLL cells, while the IC50 was not achieved in normal lymphocytes. Collectively, these data provide utility and selectivity of these agents that will inspire further and effective applications.