2-[4-bromo-N-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate | 1422986-56-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-[4-bromo-N-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate
• CAS: 1422986-56-8
• 化学式: C₁₂H₁₈BrNO₆S₂
• 分子量: 416.314
• InChiKey: XBXPYUWJDYQHHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[4-bromo-N-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate 在 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以1.1 g的产率得到4-bromo-N,N-bis(2-chloroethyl)aniline
  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
• 作为产物：
  描述：

  4-溴苯胺 在 三乙胺 、 calcium carbonate 、 sodium iodide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 2-[4-bromo-N-(2-methylsulfonyloxyethyl)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

• [EN] METHODS FOR INDUCING BIOORTHOGONAL REACTIVITY<br/>[FR] PROCÉDÉS POUR INDUIRE UNE RÉACTIVITÉ BIO-ORTHOGONALE
  申请人：FOX JOSEPH

  公开号：WO2017106427A1

  公开（公告）日：2017-06-22

  A method for catalytically converting a dihydrotetrazine 1 into a tetrazine 2, wherein one R group on the dihydrotetrazine 1 is a substituted or unsubstituted aryi, heteroaryl, alkyl, alkenyl, alkynyl, carbonyl, or heteroatom-containing group, and the other R group is selected from the group consisting of H and substituted or unsubstituted aryl, heteroaryl, alkyl, alkenyl, alkynyl, carbonyl,-or heteroatom-containing groups; 1, 2 wherein the method comprises oxidizing dihydrotetrazine 1 in a reaction medium in the presence of a catalyst and a stoichiometric oxidant.

  将二氢四氮唑1催化转化为四氮唑2的方法，其中二氢四氮唑1上的一个R基团是取代或未取代的芳基、杂环芳基、烷基、烯基、炔基、羰基或含杂原子的基团，另一个R基团选自H和取代或未取代的芳基、杂环芳基、烷基、烯基、炔基、羰基或含杂原子的基团；其中该方法包括在反应介质中在催化剂和化学计量氧化剂的存在下氧化二氢四氮唑1。
• Methods for inducing bioorthogonal reactivity
  申请人：Fox Joseph

  公开号：US10875840B2

  公开（公告）日：2020-12-29

  A method for catalytically converting a dihydrotetrazine 1 into a tetrazine 2, wherein one R group on the dihydrotetrazine 1 is a substituted or unsubstituted aryl, heteroaryl, alkyl, alkenyl, alkynyl, carbonyl, or heteroatom-containing group, and the other R group is selected from the group consisting of H and substituted or unsubstituted aryl, heteroaryl, alkyl, alkenyl, alkynyl, carbonyl,- or heteroatom-containing groups; 1, 2 wherein the method comprises oxidizing dihydrotetrazine 1 in a reaction medium in the presence of a catalyst and a stoichiometric oxidant.

  一种催化二氢四嗪1转化为四嗪2的方法，其中二氢四嗪1上的一个R基团是取代或未取代的芳基、杂芳基、烷基、烯基、炔基、羰基或含杂原子的基团，另一个R基团选自由H和取代或未取代的芳基、杂芳基、烷基、烯基、炔基、羰基或含杂原子的基团组成的组；1, 2 其中该方法包括在催化剂和定量氧化剂存在下，在反应介质中氧化二氢四嗪 1。
• METHODS FOR INDUCING BIOORTHOGONAL REACTIVITY
  申请人：FOX Joseph

  公开号：US20180362504A1

  公开（公告）日：2018-12-20

  A method for catalytically converting a dihydrotetrazine 1 into a tetrazine 2, wherein one R group on the dihydrotetrazine 1 is a substituted or unsubstituted aryl, heteroaryl, alkyl, alkenyl, alkynyl, carbonyl, or heteroatom-containing group, and the other R group is selected from the group consisting of H and substituted or unsubstituted aryl, heteroaryl, alkyl, alkenyl, alkynyl, carbonyl,—or heteroatom-containing groups; 1, 2 wherein the method comprises oxidizing dihydrotetrazine 1 in a reaction medium in the presence of a catalyst and a stoichiometric oxidant.