ethyl 3-amino-5-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate | 237435-41-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 3-amino-5-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate
• 英文别名: ethyl 3-amino-5-(4-methoxyphenyl)pyrrole-2-carboxylate
• CAS: 237435-41-5
• 化学式: C₁₄H₁₆N₂O₃
• 分子量: 260.293
• InChiKey: XLZZIQGFJUCXFY-UHFFFAOYSA-N

物化性质

• 熔点：
  173.0-174.5 °C
• 沸点：
  488.1±45.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

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：

  ethyl 3-amino-5-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate 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 114.0h， 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：

  4-甲氧基苯甲酰基乙腈 在 sodium ethanolate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 ethyl 3-amino-5-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  一系列吡咯并[3,2-d]嘧啶衍生物和相关化合物作为神经肽Y5受体拮抗剂的结构活性关系。

  摘要：

  已显示神经肽Y（NPY）在调节食物摄入和能量平衡中起重要作用。药理数据表明，Y5受体亚型有助于NPY对食欲的影响，因此Y5拮抗剂可能是治疗肥胖症的有用治疗剂。为了鉴定潜在的Y5拮抗剂，制备了一系列吡咯并[3，2-d]嘧啶衍生物，并评估了它们在体外与Y5受体结合的能力。我们在此报告这类化合物的合成与初始结构-活性关系研究。通过多种旨在修饰吡咯并[3,2-d]嘧啶铅1的取代基和杂环核的合成路线来制备目标化合物。

  DOI：

  10.1021/jm000269t

文献信息

• Compounds and methods which modulate feeding behavior and related diseases
  申请人：Amgen Inc.

  公开号：US06187777B1

  公开（公告）日：2001-02-13

  There are provided compounds, compositions and methods of use thereof in the modulation of feeding behavior, obesity, diabetes, cancer (tumor), inflammatory disorders, depression, stress related disorders, Alzheimer's disease and other disease conditions.

  提供了化合物、组合物及其使用方法，用于调节进食行为、肥胖、糖尿病、癌症（肿瘤）、炎症性疾病、抑郁症、与压力相关的疾病、阿尔茨海默病和其他疾病状况。
• Fused Heterocyclic Compound
  申请人：Ishikawa Tomoyasu

  公开号：US20070244132A1

  公开（公告）日：2007-10-18

  The present invention relates to a compound represented by the formula: wherein W is C(R 1 ) or N, each A is an optionally substituted aryl group or a heteroaryl group, X 1 is —NR 3 —Y 1 —, —O—, —S—, —SO—, —SO 2 — or —CHR 3 — wherein R 3 is a hydrogen atom or an optionally substituted aliphatic hydrocarbon group, or R 3 is optionally bonded to A to form an optionally substituted ring structure, R 1 is a hydrogen atom or an optionally substituted group bonded via a carbon atom, a nitrogen atom or an oxygen atom, R 2 is a hydrogen atom or optionally substituted group bonded via a carbon atom or a sulfur atom, or R 1 and R 2 , or R 2 and R 3 are optionally bonded to form an optionally substituted ring structure, or a salt thereof, and a tyrosine kinase inhibitor or an agent for the prophylaxis or treatment of cancer, which contains this compound or a prodrug thereof.

  本发明涉及一种化合物，其表示式为：其中W是C（R1）或N，每个A是可选取代的芳基或杂环基，X1是—NR3—Y1—、—O—、—S—、—SO—、—SO2—或—CHR3—，其中R3是氢原子或可选取代的脂肪烃基，或者R3与A可选地结合形成可选取代的环状结构，R1是氢原子或通过碳原子、氮原子或氧原子键合的可选取代基团，R2是氢原子或通过碳原子或硫原子键合的可选取代基团，或者R1和R2，或者R2和R3可选地键合形成可选取代的环状结构，或其盐，以及含有该化合物或其前药的酪氨酸激酶抑制剂或预防或治疗癌症的药物。
• Fused heterocyclic compound
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US07507740B2

  公开（公告）日：2009-03-24

  The present invention relates to a compound represented by the formula: wherein W is C(R1) or N, each A is an optionally substituted aryl group or a heteroaryl group, X1 is —NR3—Y1—, —O—, —S—, —SO—, —SO2— or —CHR3— wherein R3 is a hydrogen atom or an optionally substituted aliphatic hydrocarbon group, or R3 is optionally bonded to A to form an optionally substituted ring structure, R1 is a hydrogen atom or an optionally substituted group bonded via a carbon atom, a nitrogen atom or an oxygen atom, R2 is a hydrogen atom or optionally substituted group bonded via a carbon atom or a sulfur atom, or R1 and R2, or R2 and R3 are optionally bonded to form an optionally substituted ring structure, or a salt thereof, and a tyrosine kinase inhibitor or an agent for the prophylaxis or treatment of cancer, which contains this compound or a prodrug thereof.

  本发明涉及一种由以下公式表示的化合物：其中W为C（R1）或N，每个A为可选取代的芳基或杂环基，X1为—NR3—Y1—、—O—、—S—、—SO—、—SO2—或—CHR3—，其中R3为氢原子或可选取代的脂肪烃基，或R3可选择与A结合形成可选取代的环状结构，R1为氢原子或通过碳原子、氮原子或氧原子键合的可选取代基，R2为氢原子或通过碳原子或硫原子键合的可选取代基，或R1和R2，或R2和R3可选择结合形成可选取代的环状结构，或其盐，并且包含该化合物或其前药的酪氨酸激酶抑制剂或癌症预防或治疗剂。
• Bi- and tricyclic fused pyrimidines as tyrosine kinase inhibitors
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US08178543B2

  公开（公告）日：2012-05-15

  The present invention relates to a compound represented by the formula: wherein W is C(R1) or N, each A is an optionally substituted aryl group or a heteroaryl group, X1 is —NR3—Y1—, —O—, —S—, —SO—, —SO2— or —CHR3— wherein R3 is a hydrogen atom or an optionally substituted aliphatic hydrocarbon group, or R3 is optionally bonded to A to form an optionally substituted ring structure, R1 is a hydrogen atom or an optionally substituted group bonded via a carbon atom, a nitrogen atom or an oxygen atom, R2 is a hydrogen atom or optionally substituted group bonded via a carbon atom or a sulfur atom, or R1 and R2, or R2 and R3 are optionally bonded to form an optionally substituted ring structure, or a salt thereof, and a tyrosine kinase inhibitor or an agent for the prophylaxis or treatment of cancer, which contains this compound or a prodrug thereof.

  本发明涉及一种由以下式表示的化合物：其中W是C（R1）或N，每个A是一个可选地取代的芳基或杂环基，X1是-NR3-Y1-、-O-、-S-、-SO-、-SO2-或-CHR3-，其中R3是氢原子或可选地取代的脂肪烃基，或者R3可选择与A结合形成可选地取代的环结构，R1是氢原子或通过碳原子、氮原子或氧原子键合的可选地取代的基团，R2是氢原子或通过碳原子或硫原子键合的可选地取代的基团，或者R1和R2，或者R2和R3可选择结合形成可选地取代的环结构，或其盐，以及含有该化合物或其前药的酪氨酸激酶抑制剂或癌症预防或治疗剂。
• FUSED HETEROCYCLIC COMPOUND
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1752457B1

  公开（公告）日：2014-03-19