(E)-3-(4'-hydroxybiphenyl-3-yl)-acrylic acid | 1155663-10-7

• 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: (E)-3-(4'-hydroxybiphenyl-3-yl)-acrylic acid
• 英文别名: trans-3-(4-hydroxyphenyl)cinnamic acid；E-3-(4'-hydroxybiphenyl-3-yl)-acrylic acid；(E)-3-[3-(4-hydroxyphenyl)phenyl]prop-2-enoic acid
• CAS: 1155663-10-7
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: CWTYNHHVCGIEHV-RUDMXATFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(4'-hydroxybiphenyl-3-yl)-acrylic acid 在 盐酸羟胺 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以23%的产率得到N-hydroxy-(E)-3-[4'-hydroxybiphenyl-3-yl]-acrylamide
  参考文献：
  名称：

  Design, synthesis, and evaluation of biphenyl-4-yl-acrylohydroxamic acid derivatives as histone deacetylase (HDAC) inhibitors

  摘要：

  A series of hydroxamic acid-based histone deacetylase (HDAC) inhibitors were designed on the basis of a model of the HDAC2 binding site and synthesized. They are characterized by a cinnamic spacer, capped with a substituted phenyl group. Modifications of the spacer are also reported. In an in vitro assay with the isoenzyme HDAC2, a good correlation of the activity with the docking energy was found. In human ovarian carcinoma IGROV-1 cells, selected compounds produced significant acetylation of p53 and alpha-tubulin. Most compounds showed an antiproliferative activity comparable to that of SAHA. At equitoxic concentrations, the tested compounds were more effective than SAHA in inducing apoptotic cell death. Compounds selected for in vivo evaluation exhibited a significant antitumor activity on three tumor models at well tolerated doses, thus suggesting a good therapeutic index. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.11.005
• 作为产物：
  描述：

  methyl (E)-3-(4'-hydroxybiphenyl-3-yl)-acrylate 在 lithium hydroxide monohydrate 、 水 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以64%的产率得到(E)-3-(4'-hydroxybiphenyl-3-yl)-acrylic acid
  参考文献：
  名称：

  Design, synthesis, and evaluation of biphenyl-4-yl-acrylohydroxamic acid derivatives as histone deacetylase (HDAC) inhibitors

  摘要：

  A series of hydroxamic acid-based histone deacetylase (HDAC) inhibitors were designed on the basis of a model of the HDAC2 binding site and synthesized. They are characterized by a cinnamic spacer, capped with a substituted phenyl group. Modifications of the spacer are also reported. In an in vitro assay with the isoenzyme HDAC2, a good correlation of the activity with the docking energy was found. In human ovarian carcinoma IGROV-1 cells, selected compounds produced significant acetylation of p53 and alpha-tubulin. Most compounds showed an antiproliferative activity comparable to that of SAHA. At equitoxic concentrations, the tested compounds were more effective than SAHA in inducing apoptotic cell death. Compounds selected for in vivo evaluation exhibited a significant antitumor activity on three tumor models at well tolerated doses, thus suggesting a good therapeutic index. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.11.005

文献信息

• NOVEL OPIATE COMPOUNDS, METHODS OF MAKING AND METHODS OF USE
  申请人：Research Triangle Institute

  公开号：US20020165396A1

  公开（公告）日：2002-11-07

  The present application relates to novel opioid receptor antagonists and agonists, methods of making these compounds, and methods of use thereof.

  本申请涉及新型阿片受体拮抗剂和激动剂，制备这些化合物的方法以及它们的使用方法。
• [EN] NOVEL OPIATE COMPOUNDS, METHODS OF MAKING AND METHODS OF USE<br/>[FR] NOUVEAUX COMPOSES OPIACES ET LEURS PROCEDES DE PREPARATION ET D'UTILISATION
  申请人：RESEARCH TRIANGLE INSTITUTE

  公开号：WO1999045925A1

  公开（公告）日：1999-09-16

  (EN) The present invention relates to a class of nitrogen-containing heterocyclic compounds which bind to opioid receptors. The inventive compounds can be used to treat a variety of disease states which involve the opioid receptors.(FR) L'invention porte sur une classe de composés hétérocycliques azotés se fixant au récepteurs opioïdes et pouvant servir à traiter différentes maladies impliquant lesdits récepteurs.

  (中) 本发明涉及一类与阿片受体结合的含氮杂环化合物。这些创新化合物可用于治疗涉及阿片受体的各种疾病状态。(法) 本发明涉及一类与阿片受体结合的含氮杂环化合物，可用于治疗涉及阿片受体的各种疾病状态。
• Novel opiate compounds, methods of making and methods of use
  申请人：Research Triangle Institute

  公开号：US20020193602A1

  公开（公告）日：2002-12-19

  The present application relates to novel opioid receptor antagonists and agonists, methods of making these compounds, and methods of use thereof.

  本申请涉及新型阿片受体拮抗剂和激动剂，制备这些化合物的方法以及使用它们的方法。
• Biphenyl and Naphthyl-Phenyl Hydroxamic Acid Derivatives
  申请人：Pisano Claudio

  公开号：US20080319082A1

  公开（公告）日：2008-12-25

  Biphenyl and phenyl-naphthyl compounds bearing a hydroxamic group, which are endowed with antitumour, and anti-angiogenic activity These compounds are therefore particularly useful for the treatment of drug-resistant tumours.

  苯基联苯和苯基萘化合物带有羟肟基，具有抗肿瘤和抗血管生成活性。因此，这些化合物特别适用于治疗耐药性肿瘤。
• WO2007/383
  申请人：——

  公开号：——

  公开（公告）日：——