2-(benzo[d]isothiazol-3-ylimino)-5-(4-hydroxy-3,5-dimethoxybenzylidene)thiazolidin-4-one | 1357174-94-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(benzo[d]isothiazol-3-ylimino)-5-(4-hydroxy-3,5-dimethoxybenzylidene)thiazolidin-4-one
• 英文别名: 2-(1,2-benzothiazol-3-ylamino)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-thiazol-4-one
• CAS: 1357174-94-7
• 化学式: C₁₉H₁₅N₃O₄S₂
• 分子量: 413.478
• InChiKey: SGLGAILDRBIJLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  96.53
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  3-氨基-1,2-苯并异噻唑 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-(benzo[d]isothiazol-3-ylimino)-5-(4-hydroxy-3,5-dimethoxybenzylidene)thiazolidin-4-one
  参考文献：
  名称：

  Fragment-based design, docking, synthesis, biological evaluation and structure–activity relationships of 2-benzo/benzisothiazolimino-5-aryliden-4-thiazolidinones as cycloxygenase/lipoxygenase inhibitors

  摘要：

  Balanced modulation of several targets is one of the current strategies for the treatment of multi-factorial diseases. Based on the knowledge of inflammation mechanisms, it was inferred that the balanced inhibition of cyclooxygenase-1/cyclooxygenase-2/lipoxygenase might be a promising approach for treatment of such a multifactorial disease state as inflammation. Detection of fragments responsible for interaction with enzyme's binding site provides the basis for designing new molecules with increased affinity and selectivity. A new chemoinformatics approach was proposed and applied to create a fragment library that was used to design novel inhibitors of cycloxygenase-1/cycloxygenase-2/lipoxygenase enzymes. Potential binding sites were elucidated by docking. Synthesis of novel compounds, and the in vitro/in vivo biological testing confirmed the results of computational studies. The benzothiazolyl moiety was proved to be of great significance for developing more potent inhibitors. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.029