N-(2-chloroethyl)-N'-{3-[2-ethoxycarbonyl-5-(4-methoxyphenyl)-1H-pyrrolyl]}urea | 850145-29-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-(2-chloroethyl)-N'-{3-[2-ethoxycarbonyl-5-(4-methoxyphenyl)-1H-pyrrolyl]}urea
• 英文别名: ethyl 3-(2-chloroethylcarbamoylamino)-5-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate
• CAS: 850145-29-8
• 化学式: C₁₇H₂₀ClN₃O₄
• 分子量: 365.817
• InChiKey: BIQCLHOEDRJIKP-UHFFFAOYSA-N

物化性质

• 熔点：
  178-180 °C
• 沸点：
  564.4±50.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-chloroethyl)-N'-{3-[2-ethoxycarbonyl-5-(4-methoxyphenyl)-1H-pyrrolyl]}urea 在 氢氧化钾 、 碳酸氢钠 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 98.0h， 生成 3-[2-[4-(2-chlorophenyl)piperazin-1-yl]ethyl]-6-(4-methoxyphenyl)-1,5-dihydropyrrolo[3,2-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of 3-Arylpiperazinylalkylpyrrolo[3,2-d]pyrimidine-2,4-dione Derivatives as Novel, Potent, and Selective α₁-Adrenoceptor Ligands

  摘要：

  Novel compounds characterized by a pyrrolo [3,2-d] pyrimidine-2,4-dione (PPm) system connected through an alkyl chain to a phenylpiperazine (PPz) residue were designed as structural analogues of the alpha(1)-adrenoceptor (alpha(1)-AR) ligand RN5 (1). In this new series of derivatives an arylpyrrolo moiety has replaced the indole nucleus of RN5. Several structural modifications were performed on the PPm and PPz moieties and the connecting alkyl chain. These compounds were synthesized and tested in radioligand binding experiments where many of them showed interesting binding profiles. Some compounds, including 31, 34, and 36, displayed substantial alpha(1)-AR selectivity with respect to serotoninergic 5-HT1A and dopaminergic D-1 and D-2 receptors. Two different molecular modeling approaches (pharmacophoric mapping and quantitative structure-affinity relationship analysis) have been applied to rationalize, at a quantitative level, the relationships between affinity toward alpha(1)-ARs and the structure of the studied compounds. Several QSAR models have been reported and described, accounting for the influence of various molecular portions on such affinity data.

  DOI：

  10.1021/jm040870h
• 作为产物：
  描述：

  氯乙基异氰酸酯 、 ethyl 3-amino-5-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate 以 甲苯 为溶剂， 反应 16.0h， 以80%的产率得到N-(2-chloroethyl)-N'-{3-[2-ethoxycarbonyl-5-(4-methoxyphenyl)-1H-pyrrolyl]}urea
  参考文献：
  名称：

  Synthesis of 3-Arylpiperazinylalkylpyrrolo[3,2-d]pyrimidine-2,4-dione Derivatives as Novel, Potent, and Selective α₁-Adrenoceptor Ligands

  摘要：

  Novel compounds characterized by a pyrrolo [3,2-d] pyrimidine-2,4-dione (PPm) system connected through an alkyl chain to a phenylpiperazine (PPz) residue were designed as structural analogues of the alpha(1)-adrenoceptor (alpha(1)-AR) ligand RN5 (1). In this new series of derivatives an arylpyrrolo moiety has replaced the indole nucleus of RN5. Several structural modifications were performed on the PPm and PPz moieties and the connecting alkyl chain. These compounds were synthesized and tested in radioligand binding experiments where many of them showed interesting binding profiles. Some compounds, including 31, 34, and 36, displayed substantial alpha(1)-AR selectivity with respect to serotoninergic 5-HT1A and dopaminergic D-1 and D-2 receptors. Two different molecular modeling approaches (pharmacophoric mapping and quantitative structure-affinity relationship analysis) have been applied to rationalize, at a quantitative level, the relationships between affinity toward alpha(1)-ARs and the structure of the studied compounds. Several QSAR models have been reported and described, accounting for the influence of various molecular portions on such affinity data.

  DOI：

  10.1021/jm040870h

文献信息

• Synthesis of 3-Arylpiperazinylalkylpyrrolo[3,2-<i>d</i>]pyrimidine-2,4-dione Derivatives as Novel, Potent, and Selective α₁-Adrenoceptor Ligands
  作者：Emanuele Patanè、Valeria Pittalà、Francesco Guerrera、Loredana Salerno、Giuseppe Romeo、Maria Angela Siracusa、Filippo Russo、Fabrizio Manetti、Maurizio Botta、Ilario Mereghetti、Alfredo Cagnotto、Tiziana Mennini

  DOI：10.1021/jm040870h

  日期：2005.4.1

  Novel compounds characterized by a pyrrolo [3,2-d] pyrimidine-2,4-dione (PPm) system connected through an alkyl chain to a phenylpiperazine (PPz) residue were designed as structural analogues of the alpha(1)-adrenoceptor (alpha(1)-AR) ligand RN5 (1). In this new series of derivatives an arylpyrrolo moiety has replaced the indole nucleus of RN5. Several structural modifications were performed on the PPm and PPz moieties and the connecting alkyl chain. These compounds were synthesized and tested in radioligand binding experiments where many of them showed interesting binding profiles. Some compounds, including 31, 34, and 36, displayed substantial alpha(1)-AR selectivity with respect to serotoninergic 5-HT1A and dopaminergic D-1 and D-2 receptors. Two different molecular modeling approaches (pharmacophoric mapping and quantitative structure-affinity relationship analysis) have been applied to rationalize, at a quantitative level, the relationships between affinity toward alpha(1)-ARs and the structure of the studied compounds. Several QSAR models have been reported and described, accounting for the influence of various molecular portions on such affinity data.