ethyl 3-amino-4-(4-methoxyphenyl)furan-2-carboxylate | 455281-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl 3-amino-4-(4-methoxyphenyl)furan-2-carboxylate
• CAS: 455281-25-1
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: IVILIMYFJVKPSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：
  74.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-4-(4-methoxyphenyl)furan-2-carboxylate 在 palladium diacetate 、 sodium hydroxide 、 三苯基膦 作用下， 以 甲苯 为溶剂， 生成 3-Hydroxy-7-(4-methoxy-phenyl)-1H-furo[3,2-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  The identification and optimization of a N-hydroxy urea series of flap endonuclease 1 inhibitors

  摘要：

  Flap endonuclease-1 (FEN1) is a key enzyme involved in base excision repair (BER), a primary pathway utilized by mammalian cells to repair DNA damage. Sensitization to DNA damaging agents is a potential method for the improvement of the therapeutic window of traditional chemotherapeutics. In this paper, we describe the identification and SAR of a series of low nanomolar FEN1 inhibitors. Over 1000-fold specificity was achieved against a related endonuclease, xeroderma pigmentosum G (XPG). Two compounds from this series significantly potentiate the action of methyl methanesulfonate (MMS) and temozolamide in a bladder cancer cell line (T24). To our knowledge, these are the most potent endonuclease inhibitors reported to date. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.086
• 作为产物：
  描述：

  3-hydroxy-2-(4-methoxyphenyl)acrylonitrile sodium salt 在 1,5-二氮杂双环[4.3.0]壬-5-烯 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 ethyl 3-amino-4-(4-methoxyphenyl)furan-2-carboxylate
  参考文献：
  名称：

  新型 3-氨基-4-芳基呋喃-2-甲酸乙酯的合成

  摘要：

  描述了一种制备新型 3-氨基-4-芳基呋喃-2-羧酸乙酯的有效方法。合成通过相应的羟基丙烯腈钠盐和中间体丙二酸乙烯基醚进行。闭环的最后一步以 15% 至 40% 的收率提供了 3-氨基-4-芳基呋喃-2-羧酸乙酯。

  DOI：

  10.1055/s-2002-25772

文献信息

• Synthesis of new dipyrrolo- and furopyrrolopyrazinones related to tripentones and their biological evaluation as potential kinases (CDKs1–5, GSK-3) inhibitors
  作者：Christophe Rochais、Nghia Vu Duc、Elodie Lescot、Jana Sopkova-de Oliveira Santos、Ronan Bureau、Laurent Meijer、Patrick Dallemagne、Sylvain Rault

  DOI：10.1016/j.ejmech.2008.05.011

  日期：2009.2

  We herein describe the synthesis of novel dipyrrolo- and furopyrrolopyrazinones related to highly cytotoxic tripentones and to their oximes. The synthetic pathway involved in particular a Curtius rearrangement and a subsequent cyclisation into the title pyrazinones. The biological evaluation towards various cyclin-dependent kinases (CDKs1-5, GSK-3) highlighted a weak inhibitory activity for the oximes whose SAR was studied by a molecular modeling study. (c) 2008 Elsevier Masson SAS. All rights reserved.