ethyl 3-amino-5-(2-chlorophenyl)-1H-pyrrole-2-carboxylate | 237435-95-9

• 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-(2-chlorophenyl)-1H-pyrrole-2-carboxylate
• 英文别名: ethyl 3-amino-5-(2-chlorophenyl)pyrrole-2-carboxylate
• CAS: 237435-95-9
• 化学式: C₁₃H₁₃ClN₂O₂
• 分子量: 264.711
• InChiKey: IDAGXZGLKULQSX-UHFFFAOYSA-N

物化性质

• 熔点：
  90.0-91.5 °C
• 沸点：
  466.0±45.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  68.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-5-(2-chlorophenyl)-1H-pyrrole-2-carboxylate 在 三氯氧磷 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 2-(2-chlorophenyl)-8-oxo-5,6,7,8-tetrahydro-1H-1,4,7a-triaza-s-indacene-7-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and evaluation of tricyclic pyrrolopyrimidinones as dipeptide mimetics: Inhibition of interleukin-1β-converting enzyme

  摘要：

  The application of a tricyclic pyrrolopyrimidinone scaffold for the synthesis of peptidomimetic inhibitors of interleukin-1 beta-converting enzyme (ICE) is reported. The synthesis of the tricyclic scaffold and conversion of it to a variety of target ICE inhibitors were accomplished in 4-5 steps. In vitro biological evaluation of the tricyclic pyrrolopyrimidinones revealed fair to good ICE inhibitors, with the most active compound exhibiting an IC50 of 14 nM in a caspase-1 enzyme binding assay. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.046
• 作为产物：
  描述：

  邻氯苯乙酰腈 在 sodium ethanolate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 ethyl 3-amino-5-(2-chlorophenyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  A Short, Facile Synthesis of 5-Substituted 3-Amino-1H-pyrrole-2-carboxylates

  摘要：

  DOI：

  10.1021/jo9917902

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.
• BICYCLIC PYRIDINE AND PYRIMIDINE DERIVATIVES AS NEUROPEPTIDE Y RECEPTOR ANTAGONISTS
  申请人：Amgen Inc.

  公开号：EP1054887A1

  公开（公告）日：2000-11-29
• US6187777B1
  申请人：——

  公开号：US6187777B1

  公开（公告）日：2001-02-13
• US6583154B1
  申请人：——

  公开号：US6583154B1

  公开（公告）日：2003-06-24
• [EN] BICYCLIC PYRIDINE AND PYRIMIDINE DERIVATIVES AS NEUROPEPTIDE Y RECEPTOR ANTAGONISTS<br/>[FR] COMPOSES ET METHODES PERMETTANT DE MODULER DES CONDUITES ALIMENTAIRES ET DES PATHOLOGIES Y AFFERENTES
  申请人：AMGEN INC.

  公开号：WO1999040091A1

  公开（公告）日：1999-08-12

  (EN) 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.(FR) La présente invention concerne des compositions et des méthodes qui permettent de moduler des conduites alimentaires ainsi que l'obésité, le diabète, le cancer (tumeurs), les maladies inflammatoires, la dépression, les troubles liés au stress, la maladie d'Alzheimer et d'autres états pathologiques.