2,3-bis(phenyltellanyl)naphthoquinone | 156479-37-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-bis(phenyltellanyl)naphthoquinone
• 英文别名: 2,3-Bis(phenyltelluro)naphthalene-1,4-dione；2,3-bis(phenyltellanyl)naphthalene-1,4-dione
• CAS: 156479-37-7
• 化学式: C₂₂H₁₄O₂Te₂
• 分子量: 565.552
• InChiKey: GBWAOSVDDOPJTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 联苯二碲 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 以25%的产率得到2,3-bis(phenyltellanyl)naphthoquinone
  参考文献：
  名称：

  Synthesis and Selective Anticancer Activity of Organochalcogen Based Redox Catalysts

  摘要：

  Many tumor cells exhibit a disturbed intracellular redox state resulting in higher levels of reactive oxygen species (ROS). As these contribute to tumor initiation and sustenance, catalytic redox agents combining significant atctivity with substrate specificity promise high activity andselectivity L. Must oxidatively stressed malignant cells. We describe here the design and synthesis of novel organochalcogen based redox sensor/effector catalysts. Their selective anticancer activity at submicromolar and low micromolar concentrations was established here in a range of tumor entities in various biological systems including cell lines, primary tumor cell cultures, and animal models. In the B-cell derived chronic lymphocytic leukemia (CLL), for instance, such compounds preferentially induce apoptosis in the cancer cells while peripheral blood mononuclear cells (PBMC) from healthy donors and the subset of normal 13-cells remain largely unaffected. In support of the concept of sensor/effector based ROS amplification, we are able to demonstrate that underlying this selective activity against CI.I. cells are pre-existing, elevated ROS levels in the leukemic cells compared to their nonmalignant counterparts. Furthermore, the catalysts act in concert with certain chemotherapeutic drugs in several carcinoma cell lines to decrease cell proliferation while showing no such interactions in normal cells. Overall, the high efficacy and selectivity of. (redox) catalytic sensor/effector compounds warrant further, extensive testing toward transfer into the clinical arena.

  DOI：

  10.1021/jm100576z

文献信息

• Fan Wei-Qiang, Wang Jin, Jiang Jin-Long, Zhang Yong-Min, Youji huaxue (Org. Chem.), 13 (1993) N 6, S 612- 615
  作者：Fan Wei-Qiang, Wang Jin, Jiang Jin-Long, Zhang Yong-Min

  DOI：——

  日期：——
• Synthesis and Selective Anticancer Activity of Organochalcogen Based Redox Catalysts
  作者：Mandy Doering、Lalla A. Ba、Nils Lilienthal、Carole Nicco、Christiane Scherer、Muhammad Abbas、Abdul Ali Peer Zada、Romain Coriat、Torsten Burkholz、Ludger Wessjohann、Marc Diederich、Frederic Batteux、Marco Herling、Claus Jacob

  DOI：10.1021/jm100576z

  日期：2010.10.14

  Many tumor cells exhibit a disturbed intracellular redox state resulting in higher levels of reactive oxygen species (ROS). As these contribute to tumor initiation and sustenance, catalytic redox agents combining significant atctivity with substrate specificity promise high activity andselectivity L. Must oxidatively stressed malignant cells. We describe here the design and synthesis of novel organochalcogen based redox sensor/effector catalysts. Their selective anticancer activity at submicromolar and low micromolar concentrations was established here in a range of tumor entities in various biological systems including cell lines, primary tumor cell cultures, and animal models. In the B-cell derived chronic lymphocytic leukemia (CLL), for instance, such compounds preferentially induce apoptosis in the cancer cells while peripheral blood mononuclear cells (PBMC) from healthy donors and the subset of normal 13-cells remain largely unaffected. In support of the concept of sensor/effector based ROS amplification, we are able to demonstrate that underlying this selective activity against CI.I. cells are pre-existing, elevated ROS levels in the leukemic cells compared to their nonmalignant counterparts. Furthermore, the catalysts act in concert with certain chemotherapeutic drugs in several carcinoma cell lines to decrease cell proliferation while showing no such interactions in normal cells. Overall, the high efficacy and selectivity of. (redox) catalytic sensor/effector compounds warrant further, extensive testing toward transfer into the clinical arena.