diethyl (((3-chlorophenyl)carbonyl)amino)propanedioate

• 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: diethyl (((3-chlorophenyl)carbonyl)amino)propanedioate
• 英文别名: Diethyl 2-[(3-chlorobenzoyl)amino]propanedioate
• 化学式: C₁₄H₁₆ClNO₅
• 分子量: 313.738
• InChiKey: JVTGWNOJFFKDRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (((3-chlorophenyl)carbonyl)amino)propanedioate 在 吡啶 、 tetraphosphorus decasulfide 、 乙醇 、 sodium 作用下， 反应 4.17h， 生成 2-(3-chlorophenyl)-5-methylthiazolo[5,4-d]pyrimidin-7-one
  参考文献：
  名称：

  Exploring the 7-oxo-thiazolo[5,4-d]pyrimidine core for the design of new human adenosine A3 receptor antagonists. Synthesis, molecular modeling studies and pharmacological evaluation

  摘要：

  A new series of 5-methyl-thiazolo[5,4-d]pyrimidine-7-ones bearing different substituents at position 2 (aryl, heteroaryl and arylamino groups) was synthesized and evaluated in radioligand binding assays to determine their affinities at the human (h) A(1), A(2A), and A(3) adenosine receptors (ARs). Efficacy at the hA(2B) and antagonism of selected ligands at the hA(3) were also assessed through cAMP experiments. Some of the new derivatives exhibited good to high hA(3)AR affinity and selectivity versus all the other AR subtypes. Compound 2-(4-chlorophenyl)-5-methyl-thiazolo[5,4-d]pyrimidine-7-one 4 was found to be the most potent and selective ligand of the series (K-i hA(3) = 18 nM). Molecular docking studies of the reported derivatives were carried out to depict their hypothetical binding mode in our hA(3) receptor model. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.010
• 作为产物：
  描述：

  氨基丙二酸二乙酯盐酸盐 、 3-氯苯甲酰氯 在 碳酸氢钠 作用下， 以 乙醚 、 水 为溶剂， 反应 2.0h， 以94%的产率得到diethyl (((3-chlorophenyl)carbonyl)amino)propanedioate
  参考文献：
  名称：

  Exploring the 7-oxo-thiazolo[5,4-d]pyrimidine core for the design of new human adenosine A3 receptor antagonists. Synthesis, molecular modeling studies and pharmacological evaluation

  摘要：

  A new series of 5-methyl-thiazolo[5,4-d]pyrimidine-7-ones bearing different substituents at position 2 (aryl, heteroaryl and arylamino groups) was synthesized and evaluated in radioligand binding assays to determine their affinities at the human (h) A(1), A(2A), and A(3) adenosine receptors (ARs). Efficacy at the hA(2B) and antagonism of selected ligands at the hA(3) were also assessed through cAMP experiments. Some of the new derivatives exhibited good to high hA(3)AR affinity and selectivity versus all the other AR subtypes. Compound 2-(4-chlorophenyl)-5-methyl-thiazolo[5,4-d]pyrimidine-7-one 4 was found to be the most potent and selective ligand of the series (K-i hA(3) = 18 nM). Molecular docking studies of the reported derivatives were carried out to depict their hypothetical binding mode in our hA(3) receptor model. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.010

文献信息

• Exploring the 7-oxo-thiazolo[5,4-d]pyrimidine core for the design of new human adenosine A3 receptor antagonists. Synthesis, molecular modeling studies and pharmacological evaluation
  作者：Flavia Varano、Daniela Catarzi、Lucia Squarcialupi、Marco Betti、Fabrizio Vincenzi、Annalisa Ravani、Katia Varani、Diego Dal Ben、Ajiroghene Thomas、Rosaria Volpini、Vittoria Colotta

  DOI：10.1016/j.ejmech.2015.04.010

  日期：2015.5

  A new series of 5-methyl-thiazolo[5,4-d]pyrimidine-7-ones bearing different substituents at position 2 (aryl, heteroaryl and arylamino groups) was synthesized and evaluated in radioligand binding assays to determine their affinities at the human (h) A(1), A(2A), and A(3) adenosine receptors (ARs). Efficacy at the hA(2B) and antagonism of selected ligands at the hA(3) were also assessed through cAMP experiments. Some of the new derivatives exhibited good to high hA(3)AR affinity and selectivity versus all the other AR subtypes. Compound 2-(4-chlorophenyl)-5-methyl-thiazolo[5,4-d]pyrimidine-7-one 4 was found to be the most potent and selective ligand of the series (K-i hA(3) = 18 nM). Molecular docking studies of the reported derivatives were carried out to depict their hypothetical binding mode in our hA(3) receptor model. (C) 2015 Elsevier Masson SAS. All rights reserved.