ethyl 2,5-dimethyl-1-(p-tolyl)-1H-pyrrole-3-carboxylate

• 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 2,5-dimethyl-1-(p-tolyl)-1H-pyrrole-3-carboxylate
• 英文别名: 2,5-dimethyl-1-p-tolyl-pyrrole-3-carboxylic acid ethyl ester；2,5-Dimethyl-1-p-tolyl-pyrrol-3-carbonsaeure-aethylester；Ethyl 2,5-dimethyl-1-(4-methylphenyl)-1H-pyrrole-3-carboxylate；ethyl 2,5-dimethyl-1-(4-methylphenyl)pyrrole-3-carboxylate
• 化学式: C₁₆H₁₉NO₂
• mdl: MFCD14281884
• 分子量: 257.332
• InChiKey: YFYVWGMFZWLSNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 2,5-dimethyl-1-(p-tolyl)-1H-pyrrole-3-carboxylate 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以70%的产率得到2,5-二甲基-1-(4-甲基苯基)吡咯-3-羧酸酯
  参考文献：
  名称：

  [EN] WNT SIGNALING PATHWAY INHIBITORS FOR TREATMENTS OF DISEASE
  [FR] INHIBITEURS DE LA VOIE DE SIGNALISATION WNT POUR LE TRAITEMENT DE MALADIES

  摘要：

  提供化合物和组合物作为Wnt/β-catenin通路的抑制剂，用于治疗涉及相同通路的疾病。

  公开号：

  WO2017151786A1
• 作为产物：
  描述：

  乙酰乙酸乙酯 在 水 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 mineral oil 为溶剂， 反应 48.5h， 生成 ethyl 2,5-dimethyl-1-(p-tolyl)-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Screening of a Custom-Designed Acid Fragment Library Identifies 1-Phenylpyrroles and 1-Phenylpyrrolidines as Inhibitors of Notum Carboxylesterase Activity

  摘要：

  The Wnt family of proteins are secreted signaling proteins that play key roles in regulating cellular functions. Recently, carboxylesterase Notum was shown to act as a negative regulator of Wnt signaling by mediating the removal of an essential palmitoleate. Here we disclose two new chemical scaffolds that inhibit Notum enzymatic activity. Our approach was to create a fragment library of 250 acids for screening against Notum in a biochemical assay followed by structure determination by X-ray crystallography. Twenty fragments were identified as hits for Notum inhibition, and 14 of these fragments were shown to bind in the palmitoleate pocket of Notum. Optimization of 1-phenylpyrrole 20, guided by structure-based drug design, identified 20z as the most potent compound from this series. Similarly, the optimization of 1-phenylpyrrolidine 8 gave acid 26. This work demonstrates that inhibition of Notum activity can be achieved by small, drug-like molecules possessing favorable in vitro ADME profiles.

  DOI：

  10.1021/acs.jmedchem.0c00660

文献信息

• [EN] WNT SIGNALING PATHWAY INHIBITORS FOR TREATMENTS OF DISEASE<br/>[FR] INHIBITEURS DE LA VOIE DE SIGNALISATION WNT POUR LE TRAITEMENT DE MALADIES
  申请人：UNIV MARYLAND

  公开号：WO2017151786A1

  公开（公告）日：2017-09-08

  Compounds and compositions are provided as inhibitors of the Wnt/β-catenin pathway for the treatment of diseases that implicate the same.

  提供化合物和组合物作为Wnt/β-catenin通路的抑制剂，用于治疗涉及相同通路的疾病。
• Wnt signaling pathway inhibitors for treatments of disease
  申请人：UNIVERSITY OF MARYLAND, BALTIMORE

  公开号：US10882841B2

  公开（公告）日：2021-01-05

  Compounds and compositions are provided as inhibitors of the Wnt/β-catenin pathway for the treatment of diseases that implicate the same.

  提供了作为 Wnt/β-catenin 通路抑制剂的化合物和组合物，用于治疗涉及 Wnt/β-catenin 通路的疾病。
• Fischer; Smeykal, Chemische Berichte, 1923, vol. 56, p. 2373
  作者：Fischer、Smeykal

  DOI：——

  日期：——
• Fischer; Smeykal, Chemische Berichte, <hi>1923</hi>, vol. 56, p. 2373
  作者：Fischer、Smeykal

  DOI：——

  日期：——
• WNT SIGNALING PATHWAY INHIBITORS FOR TREATMENTS OF DISEASE
  申请人：University of Maryland, Baltimore

  公开号：EP3423452A1

  公开（公告）日：2019-01-09