ethyl 4-[3-(4-methoxybenzoyl)thioureido]benzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 4-[3-(4-methoxybenzoyl)thioureido]benzoate
• 英文别名: Ethyl 4-({[(4-methoxybenzoyl)amino]carbothioyl}amino)benzoate；ethyl 4-[(4-methoxybenzoyl)carbamothioylamino]benzoate
• 化学式: C₁₈H₁₈N₂O₄S
• 分子量: 358.418
• InChiKey: AKOMHZKUFPWVAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-[3-(4-methoxybenzoyl)thioureido]benzoate 、 丁炔二酸二甲酯 以 甲醇 为溶剂， 以71%的产率得到ethyl 4-((2Z,5Z)-2-(4-methoxybenzoylimino)-5-(2-methoxy-2-oxoethylidene)-4-oxothiazolidin-3-yl)benzoate
  参考文献：
  名称：

  Benzothiazolyl substituted iminothiazolidinones and benzamido-oxothiazolidines as potent and partly selective aldose reductase inhibitors

  摘要：

  合成了两个新系列的氧硫代噻唑丙酸酯和乙酸酯衍生物，并作为醛还原酶（ALR1）和醣醇还原酶（ALR2）抑制剂进行评估。

  DOI：

  10.1039/c4md00206g
• 作为产物：
  描述：

  大茴香酸 在 氯化亚砜 作用下， 以 丙酮 为溶剂， 生成 ethyl 4-[3-(4-methoxybenzoyl)thioureido]benzoate
  参考文献：
  名称：

  Design, synthesis, molecular docking studies and in vitro screening of ethyl 4-(3-benzoylthioureido) benzoates as urease inhibitors

  摘要：

  Thioureas are exceptionally versatile building blocks towards the synthesis of wide variety of heterocyclic systems, which also possess extensive range of pharmacological activities. The substituted benzoic acids were converted into corresponding acid chlorides, these acid chlorides were then treated with potassium thiocyanate in acetone and then the reaction mixture was refluxed for 1-2 h afford ethyl 4-( 3-benzoylthioureido)benzoates thioureas in good yields. All the newly synthesized compounds were evaluated for their urease inhibitory activities and were found to be potent inhibitors of urease enzyme. Compounds 1f and 1g were identified as the most potent urease inhibitors (IC50 0.21 and 0.13 mu M, respectively), and was 100-fold more potent than the standard inhibitors. Further molecular docking studies were carried out using the crystal structure of urease to find out the binding mode of the inhibitors with the enzyme. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2013.10.001

文献信息

• Rafique, Hummera; Saeed, Aamer; Murtaza, Shahzad, Acta poloniae pharmaceutica, 2017, vol. 74, # 4, p. 1119 - 1124
  作者：Rafique, Hummera、Saeed, Aamer、Murtaza, Shahzad、Mughal, Ehsan Ullah、Mumtaz, Amara、Maalik, Aneela

  DOI：——

  日期：——
• Benzothiazolyl substituted iminothiazolidinones and benzamido-oxothiazolidines as potent and partly selective aldose reductase inhibitors
  作者：Aamer Saeed、Yildiz Tehseen、Hummera Rafique、Norbert Furtmann、Jürgen Bajorath、Ulrich Flörke、Jamshed Iqbal

  DOI：10.1039/c4md00206g

  日期：——

  Two new series of oxothiazolidine benzoate and acetate derivatives were synthesized and evaluated as aldehyde reductase (ALR1) and aldose reductase (ALR2) inhibitors.

  合成了两个新系列的氧硫代噻唑丙酸酯和乙酸酯衍生物，并作为醛还原酶（ALR1）和醣醇还原酶（ALR2）抑制剂进行评估。
• Design, synthesis, molecular docking studies and in vitro screening of ethyl 4-(3-benzoylthioureido) benzoates as urease inhibitors
  作者：Aamer Saeed、Muhammad Siraj Khan、Hummera Rafique、Mohammad Shahid、Jamshed Iqbal

  DOI：10.1016/j.bioorg.2013.10.001

  日期：2014.2

  Thioureas are exceptionally versatile building blocks towards the synthesis of wide variety of heterocyclic systems, which also possess extensive range of pharmacological activities. The substituted benzoic acids were converted into corresponding acid chlorides, these acid chlorides were then treated with potassium thiocyanate in acetone and then the reaction mixture was refluxed for 1-2 h afford ethyl 4-( 3-benzoylthioureido)benzoates thioureas in good yields. All the newly synthesized compounds were evaluated for their urease inhibitory activities and were found to be potent inhibitors of urease enzyme. Compounds 1f and 1g were identified as the most potent urease inhibitors (IC50 0.21 and 0.13 mu M, respectively), and was 100-fold more potent than the standard inhibitors. Further molecular docking studies were carried out using the crystal structure of urease to find out the binding mode of the inhibitors with the enzyme. (C) 2013 Elsevier Inc. All rights reserved.