ethyl 3-amino-4-(4-bromophenyl)furan-2-carboxylate | 455281-23-9

• 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-bromophenyl)furan-2-carboxylate
• CAS: 455281-23-9
• 化学式: C₁₃H₁₂BrNO₃
• 分子量: 310.147
• InChiKey: HVCDJWKCOMWNQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  65.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-4-(4-bromophenyl)furan-2-carboxylate 在 sodium hydroxide 作用下， 以 甲苯 为溶剂， 生成 3-Allyloxy-7-(4-bromo-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：

  对溴苯乙腈 在 敌草腈 、 sodium methylate 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 ethyl 3-amino-4-(4-bromophenyl)furan-2-carboxylate
  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

文献信息

• Synthesis of New Ethyl 3-Amino-4-arylfuran-2-carboxylates
  作者：Vincent Lisowski、Duc Nghia Vu、Xiao Feng、Sylvain Rault

  DOI：10.1055/s-2002-25772

  日期：——

  An efficient method for the preparation of new ethyl 3-amino-4-arylfuran-2-carboxylates is described. The synthesis proceeds via the corresponding hydroxyacrylonitrile sodium salt and an intermediate malonate vinyl ether.The last step of ring closure afforded the ethyl 3-amino-4-arylfuran-2-carboxylates in 15% to 40% yields.

  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。
• 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.
• THIADIAZOLE DERIVATIVES FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES
  申请人：GRIFFIOEN Gerard

  公开号：US20090054410A1

  公开（公告）日：2009-02-26

  This invention provides specifically substituted 1,2,4-thiadiazole derivatives for use in the treatment of an α-synucleopathy such as Parkinson's disease, diffuse Lewy body disease, traumatic brain injury, amyotrophic lateral sclerosis, Niemann-Pick disease, Hallervorden-Spatz syndrome, Down syndrome, neuroaxonal dystrophy, multiple system atrophy and Alzheimer's disease. This invention also provides various methods for producing such substituted 1,2,4-thiadiazole derivatives.
• US8541406B2
  申请人：——

  公开号：US8541406B2

  公开（公告）日：2013-09-24