2,3-dichloro-4'-hydroxy-1,1'-biphenyl-4-carbaldehyde | 716344-41-1

• 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: 2,3-dichloro-4'-hydroxy-1,1'-biphenyl-4-carbaldehyde
• 英文别名: 2,3-dichloro-4-(4-hydroxyphenyl)benzaldehyde
• CAS: 716344-41-1
• 化学式: C₁₃H₈Cl₂O₂
• 分子量: 267.111
• InChiKey: XALMQGXKELQZOW-UHFFFAOYSA-N

物化性质

• 熔点：
  172-174 °C
• 沸点：
  402.2±45.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 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：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dichloro-4'-hydroxy-1,1'-biphenyl-4-carbaldehyde 在 吡啶 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 3.5h， 以100%的产率得到(E)-2,3-dichloro-4'-hydroxybiphenyl-4-carbaldehyde oxime
  参考文献：
  名称：

  ERβ Ligands. Part 2: Synthesis and structure–activity relationships of a series of 4-hydroxy-biphenyl-carbaldehyde oxime derivatives

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2004.03.028
• 作为产物：
  描述：

  2,3-二氯茴香醚 在 四(三苯基膦)钯 吡啶 、 三溴化硼 、 四氯化钛 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 8.5h， 生成 2,3-dichloro-4'-hydroxy-1,1'-biphenyl-4-carbaldehyde
  参考文献：
  名称：

  ERβ Ligands. Part 2: Synthesis and structure–activity relationships of a series of 4-hydroxy-biphenyl-carbaldehyde oxime derivatives

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2004.03.028

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。
• HYDROXY-BIPHENYL-CARBALDEHYDE OXIME DERIVATIVES AND THEIR USE AS ESTROGENIC AGENTS
  申请人：Wyeth

  公开号：EP1620392B1

  公开（公告）日：2007-06-27
• US7279600B2
  申请人：——

  公开号：US7279600B2

  公开（公告）日：2007-10-09
• 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.