3-氨基-5-(叔丁基)-1H-吡咯-2-羧酸乙酯 | 237435-98-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 3-氨基-5-(叔丁基)-1H-吡咯-2-羧酸乙酯
• 英文名称: ethyl 3-amino-5-(tert-butyl)-1H-pyrrole-2-carboxylate
• 英文别名: ethyl 3-amino-5-(tert-butyl)pyrrole-2-carboxylate；ethyl 3-amino-5-tert-butyl-1H-pyrrole-2-carboxylate
• CAS: 237435-98-2
• 化学式: C₁₁H₁₈N₂O₂
• 分子量: 210.276
• InChiKey: SJLDQQCTBUPSIG-UHFFFAOYSA-N

物化性质

• 沸点：
  350.0±42.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  3-氨基-5-(叔丁基)-1H-吡咯-2-羧酸乙酯 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 (S)-2-tert-Butyl-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：

  新戊酰基乙腈 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 3-氨基-5-(叔丁基)-1H-吡咯-2-羧酸乙酯
  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 and molecular modeling of 1H-pyrrolopyrimidine-2,4-dione derivatives as ligands for the α1-adrenoceptors
  作者：Valeria Pittalà、Maria A. Siracusa、Maria N. Modica、Loredana Salerno、Alessandro Pedretti、Giulio Vistoli、Alfredo Cagnotto、Tiziana Mennini、Giuseppe Romeo

  DOI：10.1016/j.bmc.2011.06.043

  日期：2011.9

  Three different series of 1H-pyrrolopyrimidine-2,4-dione derivatives were designed and synthesized as ligands for the alpha(1)-adrenergic receptors (alpha(1)-ARs). A microwave-assisted protocol was developed in order to improve purity and yields of some final products. The majority of the synthesized compounds, tested in binding assays, displayed alpha(1)-AR affinities in the nanomolar range. Highest affinity values were found in derivatives 10b and 10c (K-i = 1.4 nM for both) whereas compound 10e was endowed with the best profile in term of alpha(1)-AR affinity (K-i = 2.71 nM) coupled with high selectivity towards 5-HT1A receptors (K-i > 10,000). Molecular docking studies were performed on human alpha(1)-ARs and human 5-HT1A receptors in order to rationalize the observed experimental affinity and selectivity; these computational studies helped to clarify molecular requirements for the design of high-selective alpha(1)-adrenergic ligands. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.