N-(2-chloroethyl)-N'-<3-<(2-methoxycarbonyl)benzothienyl>>urea | 152032-94-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: N-(2-chloroethyl)-N'-<3-<(2-methoxycarbonyl)benzothienyl>>urea
• 英文别名: 3-[[[(2-Chloroethyl)amino]carbonyl]amino]benzo[b]thiophene-2-carboxylic acid methyl ester；methyl 3-(2-chloroethylcarbamoylamino)-1-benzothiophene-2-carboxylate
• CAS: 152032-94-5
• 化学式: C₁₃H₁₃ClN₂O₃S
• 分子量: 312.777
• InChiKey: DVUZHAOBPZEULN-UHFFFAOYSA-N

物化性质

• 沸点：
  465.0±45.0 °C(Predicted)
• 密度：
  1.417±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  95.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-chloroethyl)-N'-<3-<(2-methoxycarbonyl)benzothienyl>>urea 在 sodium hydride 作用下， 反应 27.33h， 生成 3-<2-<4-(2-methoxyphenyl)piperazin-1-yl>ethyl>-1-methylpyrimido<5,4-b>benzothiophen-2,4-dione
  参考文献：
  名称：

  Pyrimido[5,4-b]benzofuran and pyrimido[5,4-b]benzothiophene derivatives Ligands for α1-and 5HT1A-receptors

  摘要：

  A number of 3-phenylpiperazinylethyl pyrimido[5,4-b]benzofuran-2,4-dione and pyrimido[5,4-b]benzothiophene-2,4-dione derivatives 5-15 were designed as bioisosters of the previously reported pyrimido[5,4-b]indole-2,4-diones and synthesized starting from the 3-amino-2-carboxybenzofuran and benzothiophene ethyl and methyl esters respectively. They were evaluated for their in vitro alpha1-adrenoceptor and 5HT1A-receptor affinities by radioligand receptor binding assays. All target compounds showed good to excellent affinities for the alpha1-adrenoceptor with K(i) values in the subnanomolar range. Some compounds were also good ligands for the 5HT1A-receptor with K(i) values in the nanomolar range. 3-[2-[4-(2-Methoxyphenyl)piperazin-1-yl]ethyl]-1-methyl pyrimido[5,4-b]benzothiophen-2,4-dione 15 was the most active derivative in displacing [H-3]-8-OH-DPAT from rat hippocampal membranes. There is evidence suggesting that the N1 methyl group of the tricyclic moiety of the title compounds is probably able to undergo a Van der Waals interaction at the 5HT1A-receptor binding site but not at the alpha1-adrenoceptor active site.

  DOI：

  10.1016/0223-5234(93)90017-9
• 作为产物：
  描述：

  氯乙基异氰酸酯 、 3-氨基苯并[b]噻吩-2-羧酸甲酯 以 甲苯 为溶剂， 反应 1.0h， 以63%的产率得到N-(2-chloroethyl)-N'-<3-<(2-methoxycarbonyl)benzothienyl>>urea
  参考文献：
  名称：

  Pyrimido[5,4-b]benzofuran and pyrimido[5,4-b]benzothiophene derivatives Ligands for α1-and 5HT1A-receptors

  摘要：

  A number of 3-phenylpiperazinylethyl pyrimido[5,4-b]benzofuran-2,4-dione and pyrimido[5,4-b]benzothiophene-2,4-dione derivatives 5-15 were designed as bioisosters of the previously reported pyrimido[5,4-b]indole-2,4-diones and synthesized starting from the 3-amino-2-carboxybenzofuran and benzothiophene ethyl and methyl esters respectively. They were evaluated for their in vitro alpha1-adrenoceptor and 5HT1A-receptor affinities by radioligand receptor binding assays. All target compounds showed good to excellent affinities for the alpha1-adrenoceptor with K(i) values in the subnanomolar range. Some compounds were also good ligands for the 5HT1A-receptor with K(i) values in the nanomolar range. 3-[2-[4-(2-Methoxyphenyl)piperazin-1-yl]ethyl]-1-methyl pyrimido[5,4-b]benzothiophen-2,4-dione 15 was the most active derivative in displacing [H-3]-8-OH-DPAT from rat hippocampal membranes. There is evidence suggesting that the N1 methyl group of the tricyclic moiety of the title compounds is probably able to undergo a Van der Waals interaction at the 5HT1A-receptor binding site but not at the alpha1-adrenoceptor active site.

  DOI：

  10.1016/0223-5234(93)90017-9