5-[(4-hydroxyphenyl)methylidene]-2-(1,3-thiazol-2-ylamino)-1,3-thiazol-4-one | 889102-56-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-[(4-hydroxyphenyl)methylidene]-2-(1,3-thiazol-2-ylamino)-1,3-thiazol-4-one
• CAS: 889102-56-1
• 化学式: C₁₃H₉N₃O₂S₂
• 分子量: 303.365
• InChiKey: OLCHTIJXNVKOCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对羟基苯甲醛 、 2-(thiazol-2-ylimino)thiazolidin-4-one 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 生成 5-[(4-hydroxyphenyl)methylidene]-2-(1,3-thiazol-2-ylamino)-1,3-thiazol-4-one
  参考文献：
  名称：

  2-Thiazolylimino/Heteroarylimino-5-arylidene-4-thiazolidinones as New Agents with SHP-2 Inhibitory Action

  摘要：

  SHP-2, a nonreceptor protein tyrosine phosphatase encoded by the PTPN11 gene, mediates cell signaling by growth factors and cytokines via the RAS/MAP kinase pathway. Somatic mutations in PTPN11 gene account for approximately 18% of juvenile myelomonocytic leukemia (JMML) patients. Moreover, SHP-2 mutations leading to continuously active enzyme were found in more than 50% of Noonan syndrome patients and are considered to be responsible for the high tendency of these patients to juvenile leukemias and other cancer types. Recently SHP-2 became a new drug target, but till flow little has been done in this field. In the present study, 172-thiazolylimino/heteroarylimino-5-arylidene-4-thiazolidinones divided into three series of derivatives bearing thiazole-, benzo[d]thiazole-, and benzo[d]isothizole rings were tested for SHP-2 inhibitory activity. Most of the compounds were good SHP-2 inhibitors. Benzo[d]thiazole derivatives exhibited the best inhibitory action. Docking studies revealed that hydrophobic interactions and hydrogen bond formation stabilize enzyme-inhibitor complex.

  DOI：

  10.1021/jm8004306