N-(3-chloropropyl)-N'-[3-[2-ethoxycarbonyl-5-(4-methylphenyl)-1H-pyrrolyl]]urea | 850145-28-7

• 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-(3-chloropropyl)-N'-[3-[2-ethoxycarbonyl-5-(4-methylphenyl)-1H-pyrrolyl]]urea
• 英文别名: ethyl 3-(3-chloropropylcarbamoylamino)-5-(4-methylphenyl)-1H-pyrrole-2-carboxylate
• CAS: 850145-28-7
• 化学式: C₁₈H₂₂ClN₃O₃
• 分子量: 363.844
• InChiKey: WQSZSBRKMRSIEN-UHFFFAOYSA-N

物化性质

• 熔点：
  212-214 °C
• 沸点：
  558.3±50.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-chloropropyl)-N'-[3-[2-ethoxycarbonyl-5-(4-methylphenyl)-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-{3-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-propyl}-6-p-tolyl-1,5-dihydro-pyrrolo[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：

  对甲苯酰乙腈 在 sodium ethanolate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 34.0h， 生成 N-(3-chloropropyl)-N'-[3-[2-ethoxycarbonyl-5-(4-methylphenyl)-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