(Z)-2-(4-Bromo-phenyl)-3-hydroxy-acrylonitrile | 89333-18-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-2-(4-Bromo-phenyl)-3-hydroxy-acrylonitrile
• 英文别名: 2-(4-Bromophenyl)-3-hydroxyacrylonitrile；(Z)-2-(4-bromophenyl)-3-hydroxyprop-2-enenitrile
• CAS: 89333-18-6
• 化学式: C₉H₆BrNO
• 分子量: 224.057
• InChiKey: RLNLEKCYESWZSJ-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-2-(4-Bromo-phenyl)-3-hydroxy-acrylonitrile 在 敌草腈 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.0h， 生成
  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 、 甲酸乙酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (Z)-2-(4-Bromo-phenyl)-3-hydroxy-acrylonitrile
  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

• US7468241B1
  申请人：——

  公开号：US7468241B1

  公开（公告）日：2008-12-23
• 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.