3-氟-4'-羟基联苯-4-甲醛 | 716344-28-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氟-4'-羟基联苯-4-甲醛
• 英文名称: 3-fluoro-4'-hydroxybiphenyl-4-carbaldehyde
• 英文别名: 3-fluoro-4'-hydroxy-1,1'-biphenyl-4-carbaldehyde；2-fluoro-4-(4-hydroxyphenyl)benzaldehyde
• CAS: 716344-28-4
• 化学式: C₁₃H₉FO₂
• 分子量: 216.212
• InChiKey: LXGCQYMERYZRJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氟-4'-羟基联苯-4-甲醛 在 吡啶 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以20 mg的产率得到3-fluoro-4'-hydroxy-1,1'-biphenyl-4-carbaldehyde oxime
  参考文献：
  名称：

  Biphenyl C-cyclopropylalkylamides: New scaffolds for targeting estrogen receptor β

  摘要：

  The C-cyclopropylalkylamide scaffold was previously identified as a new structural framework for antiestrogens. A second generation library provided three compounds that bind estrogen receptor ( ER) a. Further screening of this library identified an ER beta hit and inspired another round of SAR. A new focused library was tested for binding to the ERs, and for effects on the growth of breast cancer cell lines and protein levels of common cell cycle regulators. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.075
• 作为产物：
  描述：

  3-fluoro-4'-methoxybiphenyl-4-carbaldehyde 在 三溴化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 3-氟-4'-羟基联苯-4-甲醛
  参考文献：
  名称：

  Biphenyl C-cyclopropylalkylamides: New scaffolds for targeting estrogen receptor β

  摘要：

  The C-cyclopropylalkylamide scaffold was previously identified as a new structural framework for antiestrogens. A second generation library provided three compounds that bind estrogen receptor ( ER) a. Further screening of this library identified an ER beta hit and inspired another round of SAR. A new focused library was tested for binding to the ERs, and for effects on the growth of breast cancer cell lines and protein levels of common cell cycle regulators. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.075

文献信息

• Hydroxy-biphenyl-carbaldehyde oxime derivatives and their use as estrogenic agents
  申请人：Mewshaw Eric Richard

  公开号：US20050020676A1

  公开（公告）日：2005-01-27

  This invention provides estrogen receptor modulators having the structure: wherein R 1 to R 6 and R 8 are as defined in the specification; or a pharmaceutically acceptable salt thereof.

  本发明提供了具有以下结构的雌激素受体调节剂：其中R1至R6和R8的定义如规范中所述；或其药学上可接受的盐。
• Hydroxy-Biphenyl-Carbaldehyde Oxime Derivatives and Their Use As Estrogenic Agents
  申请人：Mewshaw Eric Richard

  公开号：US20080033049A1

  公开（公告）日：2008-02-07

  This invention provides estrogen receptor modulators having the structure: wherein R 1 to R 6 and R 8 are as defined in the specification; or a pharmaceutically acceptable salt thereof.

  该发明提供了具有以下结构的雌激素受体调节剂：其中R1至R6和R8如规范中定义；或其药用盐。
• [EN] HYDROXY-BIPHENYL-CARBALDEHYDE OXIME DERIVATIVES AND THEIR USE AS ESTROGENIC AGENTS<br/>[FR] DERIVES D'OXIME HYDROXY-BIPHENYL-CARBALDEHYDE ET LEUR UTILISATION COMME AGENTS OESTROGENES
  申请人：WYETH CORP

  公开号：WO2004099122A3

  公开（公告）日：2005-02-17
• ERβ Ligands. Part 2: Synthesis and structure–activity relationships of a series of 4-hydroxy-biphenyl-carbaldehyde oxime derivatives
  作者：Cuijian Yang、Richard Edsall、Heather A Harris、Xiaochun Zhang、Eric S Manas、Richard E Mewshaw

  DOI：10.1016/j.bmc.2004.03.028

  日期：2004.5

  A series of biphenyl carbaldehyde oximes (6) was prepared and shown to have significant selectivity for the estrogen receptor-beta (ERbeta). The exploitation of the oxime moiety as a hydrogen bond donating group, which mimicked the C-ring of genistein makes these compounds unique. Molecular modeling studies showed the oxime moiety hydrogen bonding to the histidine residue, which was supported by the structure-activity relationships. The most potent compounds in this study had IC50 values in a radio-liaand binding assay of between 8-35 nM. Among the most selective compounds were 6i and 6s (49- and 31-fold ERbeta selective, respectively). (C) 2004 Elsevier Ltd. All rights reserved.
• HYDROXY-BIPHENYL-CARBALDEHYDE OXIME DERIVATIVES AND THEIR USE AS ESTROGENIC AGENTS
  申请人：Wyeth

  公开号：EP1620392A2

  公开（公告）日：2006-02-01