4-[(1,1,3-Trioxo-2,3-dihydro-1λ6,2-benzothiazol-2-yl)methyl]benzoyl chloride | 1612763-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 4-[(1,1,3-Trioxo-2,3-dihydro-1λ6,2-benzothiazol-2-yl)methyl]benzoyl chloride
• 英文别名: 4-[(1,1,3-Trioxo-2,3-dihydro-1λ⁶,2-benzothiazol-2-yl)methyl]benzoyl chloride
• CAS: 1612763-47-9
• 化学式: C₁₅H₁₀ClNO₄S
• 分子量: 335.768
• InChiKey: LXHVZHSMNFOBDO-UHFFFAOYSA-N

物化性质

• 沸点：
  545.3±60.0 °C(Predicted)
• 密度：
  1.544±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.52
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-[(1,1,3-Trioxo-2,3-dihydro-1λ6,2-benzothiazol-2-yl)methyl]benzoyl chloride 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 生成 tert-Butyl N-[2-(furan-2-yl)ethyl]-N-{4-[(1,1,3-trioxo-2,3-dihydro-1λ⁶,2-benzothiazol-2-yl)methyl]benzoyl}carbamate
  参考文献：
  名称：

  Saccharin Derivatives as Inhibitors of Interferon-Mediated Inflammation

  摘要：

  A series of novel, saccharin-based antagonists have been identified for the interferon signaling pathway. Through in vitro high-throughput screening with the Colorado Center for Drug Discovery (C2D2) Pilot Library, we identified hit compound 1, which was the basis for extensive structure-activity relationship studies. Our efforts produced a lead anti-inflammatory compound, tert-butyl N-(furan-2-ylmethyl)-N-{4-[(1,1,3-trioxo-2,3-dihydro-1λ(6),2-benzothiazol-2-yl)methyl]benzoyl}carbamate CU-CPD103 (103), as a potent inhibitor using an established nitric oxide (NO) signaling assay. With further studies of its inhibitory mechanisms, we demonstrated that 103 carries out this inhibition through the JAK/STAT1 pathway, providing a drug-like small molecule inflammation suppressant for possible therapeutic uses.

  DOI：

  10.1021/jm500409k
• 作为产物：
  描述：

  4-[(1,1,3-Trioxo-2,3-dihydro-1λ⁶,2-benzothiazol-2-yl)methyl]benzoic acid 在 氯化亚砜 作用下， 反应 3.0h， 以99%的产率得到4-[(1,1,3-Trioxo-2,3-dihydro-1λ6,2-benzothiazol-2-yl)methyl]benzoyl chloride
  参考文献：
  名称：

  Saccharin Derivatives as Inhibitors of Interferon-Mediated Inflammation

  摘要：

  A series of novel, saccharin-based antagonists have been identified for the interferon signaling pathway. Through in vitro high-throughput screening with the Colorado Center for Drug Discovery (C2D2) Pilot Library, we identified hit compound 1, which was the basis for extensive structure-activity relationship studies. Our efforts produced a lead anti-inflammatory compound, tert-butyl N-(furan-2-ylmethyl)-N-{4-[(1,1,3-trioxo-2,3-dihydro-1λ(6),2-benzothiazol-2-yl)methyl]benzoyl}carbamate CU-CPD103 (103), as a potent inhibitor using an established nitric oxide (NO) signaling assay. With further studies of its inhibitory mechanisms, we demonstrated that 103 carries out this inhibition through the JAK/STAT1 pathway, providing a drug-like small molecule inflammation suppressant for possible therapeutic uses.

  DOI：

  10.1021/jm500409k