2-(4-methoxy-phenyl)-3-oxo-propionitrile | 89333-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-methoxy-phenyl)-3-oxo-propionitrile
• 英文别名: (Z)-3-hydroxy-2-(4-methoxyphenyl)prop-2-enenitrile
• CAS: 89333-17-5
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: MDNQHMUKHUIUGZ-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-methoxy-phenyl)-3-oxo-propionitrile 在 敌草腈 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 ethyl 3-amino-4-(4-methoxyphenyl)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
• 作为产物：
  描述：

  对甲氧基苯乙腈 、 甲酸乙酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 2-(4-methoxy-phenyl)-3-oxo-propionitrile
  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

• The action of substituted formamides on arylformylacetonitriles
  作者：J.D. Bonafede、R.R. Matuda

  DOI：10.1016/0040-4020(72)80074-7

  日期：1972.1

  The reaction between phenyl- or p-methoxy phenylformylacetonitrile and monosubstituted formamides results in enaminonitriles. In some instances a simultaneous deformylation is observed. Formic acid is produced during the reaction and its origin was investigated.

  苯基或对甲氧基苯基甲酰基乙腈与单取代甲酰胺之间的反应产生烯氨基腈。在某些情况下，观察到同时的去甲酰基化。在反应过程中产生甲酸，并对其来源进行了研究。
• KIRSCH, G.;CAGNIANT, D.;CAGNIANT, P., J. HETEROCYCL. CHEM., 1982, 19, N 2, 443-445
  作者：KIRSCH, G.、CAGNIANT, D.、CAGNIANT, P.

  DOI：——

  日期：——
• The identification and optimization of a N-hydroxy urea series of flap endonuclease 1 inhibitors
  作者：L. Nathan Tumey、David Bom、Bayard Huck、Elizabeth Gleason、Jianmin Wang、Daniel Silver、Kurt Brunden、Sherry Boozer、Stephen Rundlett、Bruce Sherf、Steven Murphy、Tom Dent、Christina Leventhal、Andrew Bailey、John Harrington、Youssef L. Bennani

  DOI：10.1016/j.bmcl.2004.10.086

  日期：2005.1

  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.