3-Hydroxy-4-methylisothiazol | 25629-60-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-Hydroxy-4-methylisothiazol
• 英文别名: 4-methyl-isothiazol-3-one；4-methyl-1,2-thiazol-3-one
• CAS: 25629-60-1
• 化学式: C₄H₅NOS
• 分子量: 115.156
• InChiKey: DXPMELADVQYNOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Hydroxy-4-methylisothiazol 、 异氰酸乙酯 以 苯 为溶剂， 反应 18.0h， 生成 4-methyl-3-oxo-3H-isothiazole-2-carboxylic acid ethylamide
  参考文献：
  名称：

  Lewis,S.N. et al., Journal of Heterocyclic Chemistry, 1971, vol. 8, p. 587 - 589

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(2-Carbamoyl-propyldisulfanyl)-2-methyl-propionamide 在 氯化亚砜 作用下， 以 乙酸乙酯 为溶剂， 以14%的产率得到5-chloro-4-methyl-2,3-dihydro-1,2-thiazol-3-one
  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

• Lewis,S.N. et al., Journal of Heterocyclic Chemistry, 1971, vol. 8, p. 587 - 589
  作者：Lewis,S.N. et al.

  DOI：——

  日期：——
• 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.