2-amino-3-ethoxycarbonyl-5-(2-methoxy-phenyl)-1H-pyrrole | 173458-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-amino-3-ethoxycarbonyl-5-(2-methoxy-phenyl)-1H-pyrrole
• 英文别名: ethyl 2-amino-5-(2-methoxyphenyl)-1H-pyrrole-3-carboxylate
• CAS: 173458-96-3
• 化学式: C₁₄H₁₆N₂O₃
• 分子量: 260.293
• InChiKey: WYOIODVYTKHXFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  77.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-3-ethoxycarbonyl-5-(2-methoxy-phenyl)-1H-pyrrole 在 氢氧化钾 、 碳酸氢钠 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 33.0h， 生成 3-{2-[4-(2-Chloro-phenyl)-piperazin-1-yl]-ethyl}-6-(2-methoxy-phenyl)-1,7-dihydro-pyrrolo[2,3-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  3-Arylpiperazinylethyl-1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione derivatives as novel, high-affinity and selective α1-adrenoceptor ligands

  摘要：

  The discovery of a new series of selective and high-affinity alpha(1)-adrenoceptor (alpha(1)-AR) ligands, characterized by a 1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione system, is described in this paper. Some synthesized compounds, including 20, 22, and 30, displayed affinity in the nanomolar range for alpha(1)-ARs and substantial selectivity with respect to 5-HT1A and dopaminergic D-1 and D-2 receptors. Functional assays, performed on selected derivatives, showed antagonistic properties. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.027
• 作为产物：
  描述：

  3-乙氧基-3-亚氨基丙酸乙酯盐酸盐 在 potassium carbonate 、 氯化铵 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 2-amino-3-ethoxycarbonyl-5-(2-methoxy-phenyl)-1H-pyrrole
  参考文献：
  名称：

  3-Arylpiperazinylethyl-1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione derivatives as novel, high-affinity and selective α1-adrenoceptor ligands

  摘要：

  The discovery of a new series of selective and high-affinity alpha(1)-adrenoceptor (alpha(1)-AR) ligands, characterized by a 1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione system, is described in this paper. Some synthesized compounds, including 20, 22, and 30, displayed affinity in the nanomolar range for alpha(1)-ARs and substantial selectivity with respect to 5-HT1A and dopaminergic D-1 and D-2 receptors. Functional assays, performed on selected derivatives, showed antagonistic properties. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.027

文献信息

• Pyrrolopyrimidines and processes for the preparation thereof
  申请人：Novartis AG

  公开号：US06140332A1

  公开（公告）日：2000-10-31

  Described are 7H-pyrrolo[2,3-d]pyrimidine derivatives of formula I ##STR1## wherein the symbols are as defined in claim 1. Those compounds inhibit tyrosine protein kinase and can be used in the treatment of hyperproliferative diseases, for example tumour diseases.

  描述了式I的7H-吡咯并[2,3-d]嘧啶衍生物##STR1##，其中符号如权利要求1所定义。这些化合物抑制酪氨酸蛋白激酶，可用于治疗高增殖性疾病，例如肿瘤疾病。
• PYRROLOPYRIMIDINES AND PROCESSES FOR THE PREPARATION THEREOF
  申请人：Novartis AG

  公开号：EP0836605B1

  公开（公告）日：2002-02-06
• US6140332A
  申请人：——

  公开号：US6140332A

  公开（公告）日：2000-10-31
• 3-Arylpiperazinylethyl-1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione derivatives as novel, high-affinity and selective α1-adrenoceptor ligands
  作者：Valeria Pittalà、Giuseppe Romeo、Loredana Salerno、Maria Angela Siracusa、Maria Modica、Luisa Materia、Ilario Mereghetti、Alfredo Cagnotto、Tiziana Mennini、Gabriella Marucci、Piero Angeli、Filippo Russo

  DOI：10.1016/j.bmcl.2005.09.027

  日期：2006.1

  The discovery of a new series of selective and high-affinity alpha(1)-adrenoceptor (alpha(1)-AR) ligands, characterized by a 1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione system, is described in this paper. Some synthesized compounds, including 20, 22, and 30, displayed affinity in the nanomolar range for alpha(1)-ARs and substantial selectivity with respect to 5-HT1A and dopaminergic D-1 and D-2 receptors. Functional assays, performed on selected derivatives, showed antagonistic properties. (c) 2005 Elsevier Ltd. All rights reserved.