4-[(1,1-dioxo-2,3-dihydro-1λ⁶,2-benzothiazol-2-yl)methyl]-N-(furan-2-ylmethyl)benzamide | 1612763-32-2

• 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-dioxo-2,3-dihydro-1λ⁶,2-benzothiazol-2-yl)methyl]-N-(furan-2-ylmethyl)benzamide
• 英文别名: 4-[(1,1-dioxo-3H-1,2-benzothiazol-2-yl)methyl]-N-(furan-2-ylmethyl)benzamide
• CAS: 1612763-32-2
• 化学式: C₂₀H₁₈N₂O₄S
• 分子量: 382.44
• InChiKey: QWPXLIQZYYDCJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  88
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-Butyl N-{4-[(1,1-dioxo-2,3-dihydro-1λ⁶,2-benzothiazol-2-yl)methyl]benzoyl}-N-(furan-2-ylmethyl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到4-[(1,1-dioxo-2,3-dihydro-1λ⁶,2-benzothiazol-2-yl)methyl]-N-(furan-2-ylmethyl)benzamide
  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

文献信息

• Saccharin Derivatives as Inhibitors of Interferon-Mediated Inflammation
  作者：Adam Csakai、Christina Smith、Emily Davis、Alexander Martinko、Sara Coulup、Hang Yin

  DOI：10.1021/jm500409k

  日期：2014.6.26

  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.