[(2,3,4-Trimethoxyphenyl)methylideneamino]thiourea

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [(2,3,4-Trimethoxyphenyl)methylideneamino]thiourea
• 化学式: C₁₁H₁₅N₃O₃S
• mdl: MFCD00022155
• 分子量: 269.324
• InChiKey: KFAOIFISKSIYPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2,3,4-Trimethoxyphenyl)methylideneamino]thiourea 在 iron(III) chloride hexahydrate 、 N,N'-羰基二咪唑 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Synthesis, bioevaluation and docking study of 5-substitutedphenyl-1,3,4-thiadiazole-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents

  摘要：

  Since the first histone deacetylase (HDAC) inhibitor (Zolinza®, widely known as suberoylanilide hydroxamic acid; SAHA) was approved by the Food and Drug Administration for the treatment of T-cell lymphoma in 2006, the search for newer HDAC inhibitors has attracted a great deal of interest of medicinal chemists worldwide. As a continuity of our ongoing research in this area, we designed and synthesized a series of 5-substitutedphenyl-1,3,4-thiadiazole-based hydroxamic acids as analogues of SAHA and evaluated their biological activities. A number of compounds in this series, for example, N(1)-hydroxy-N(8)-(5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl)octandiamide (5b), N(1)-hydroxy-N(8)-(5-(3-chlorophenyl-1,3,4-thiadiazol-2-yl)octandiamide (5c) and N(1)-hydroxy-N(8)-(5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl)octandiamide (5d), were found to possess potent anticancer cytotoxicity and HDAC inhibition effects. Compounds 5b-d were generally two- to five-fold more potent in terms of cytotoxicity compared to SAHA against five cancer cell lines tested. Docking studies revealed that these hydroxamic acid displayed higher affinities than SAHA toward HDAC8.

  DOI：

  10.3109/14756366.2013.832238
• 作为产物：
  描述：

  氨基硫脲 、 2,3,4-三甲氧基苯甲醛 以 乙醇 为溶剂， 生成 [(2,3,4-Trimethoxyphenyl)methylideneamino]thiourea
  参考文献：
  名称：

  A simple sequential one-pot synthesis of 4-aryl thiazole-based Schiff bases

  摘要：

  DOI：

  10.1080/00397911.2023.2282591