3-bromo-7,8-dichloro-2,3-dihydrothiochromen-4-one-1-oxide | 1612925-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫铬烷
• 英文名称: 3-bromo-7,8-dichloro-2,3-dihydrothiochromen-4-one-1-oxide
• CAS: 1612925-37-7
• 化学式: C₉H₅BrCl₂O₂S
• 分子量: 328.014
• InChiKey: DLZWPDGKTZHIJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-bromo-7,8-dichloro-2,3-dihydrothiochromen-4-one-1-oxide 、 氨基硫脲 以 1,4-二氧六环 为溶剂， 反应 48.0h， 生成 6,7-dichloro-2-hydrazineyl-4H-thiochromeno[4,3-d]thiazole 5-oxide
  参考文献：
  名称：

  Synthesis of Rigidified eIF4E/eIF4G Inhibitor-1 (4EGI-1) Mimetic and Their in Vitro Characterization as Inhibitors of Protein–Protein Interaction

  摘要：

  The 4EGI-1 is the prototypic inhibitor of eIF4E/eIF4G interaction, a potent inhibitor of translation initiation in vitro and in vivo and an efficacious anticancer agent in animal models of human cancers. We report on the design, synthesis, and in vitro characterization of a series of rigidified mimetic of this prototypic inhibitor in which the phenyl in the 2-(4-(3,4-dichlorophenyl)thiazol-2-yl) moiety was bridged into a tricyclic system. The bridge consisted one of the following: ethylene, methylene oxide, methylenesulfide, methylenesulfoxide, and methylenesulfone. Numerous analogues in this series were found to be markedly more potent than the parent prototypic inhibitor in the inhibition of eIF4E/eIF4G interaction, thus preventing the eIF4F complex formation, a rate limiting step in the translation initiation cascade in eukaryotes, and in inhibition of human cancer cell proliferation.

  DOI：

  10.1021/jm401733v
• 作为产物：
  描述：

  3-bromo-7,8-dichloro-2,3-dihydrothiochromen-4-one 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 3-bromo-7,8-dichloro-2,3-dihydrothiochromen-4-one-1-oxide
  参考文献：
  名称：

  Synthesis of Rigidified eIF4E/eIF4G Inhibitor-1 (4EGI-1) Mimetic and Their in Vitro Characterization as Inhibitors of Protein–Protein Interaction

  摘要：

  The 4EGI-1 is the prototypic inhibitor of eIF4E/eIF4G interaction, a potent inhibitor of translation initiation in vitro and in vivo and an efficacious anticancer agent in animal models of human cancers. We report on the design, synthesis, and in vitro characterization of a series of rigidified mimetic of this prototypic inhibitor in which the phenyl in the 2-(4-(3,4-dichlorophenyl)thiazol-2-yl) moiety was bridged into a tricyclic system. The bridge consisted one of the following: ethylene, methylene oxide, methylenesulfide, methylenesulfoxide, and methylenesulfone. Numerous analogues in this series were found to be markedly more potent than the parent prototypic inhibitor in the inhibition of eIF4E/eIF4G interaction, thus preventing the eIF4F complex formation, a rate limiting step in the translation initiation cascade in eukaryotes, and in inhibition of human cancer cell proliferation.

  DOI：

  10.1021/jm401733v