(E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-bromocinnamic acid | 540779-16-6

• 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: (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-bromocinnamic acid
• 英文别名: (E)-3-[4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-bromophenyl]prop-2-enoic acid
• CAS: 540779-16-6
• 化学式: C₂₅H₂₅BrO₃
• 分子量: 453.376
• InChiKey: HKUSIDVVDBKDGU-QHHAFSJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-溴-3-硝基苯甲醛 在 四(三苯基膦)钯 、 tin(II) chloride dihdyrate 、 lithium hydroxide monohydrate 、 己基亚硝酸盐 、 三溴甲烷 、 三溴化硼 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 48.58h， 生成 (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-bromocinnamic acid
  参考文献：
  名称：

  Analogues of Orphan Nuclear Receptor Small Heterodimer Partner Ligand and Apoptosis Inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic Acid. 2. Impact of 3-Chloro Group Replacement on Inhibition of Proliferation and Induction of Apoptosis of Leukemia and Cancer Cell Lines

  摘要：

  The parent phenol of adapalene and its (E)-cinnamic acid analogue were found to induce cancer cell apoptosis but cause adverse systemic effects when administered to mice. In contrast, their respective 5-Cl- and 3-Cl-substituted analogues had their adverse effects mitigated without a comparable loss of cancer cell inhibitory activity. As a result, pharmacologic space in this region of the cinnamic phenyl ring scaffold was explored. Various substituents were introduced, and their effects on cancer, cell proliferation and viability were evaluated. Cinnamic acids having 3-Br, CN, NO2, NH2, OMe, and N-3 groups had activity comparable to that of 4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-chlorocinnamic acid. A comparative molecular field analysis study indicated that introduction of an H-bond acceptor at position 3 of the central phenyl ring would favor inhibition of leukemia cell viability, and docking suggested its hydrogen bonding with a polar group in a small heterodimer partner homology model. The 3-CN, NO2, NH2, and OH analogues also inhibited MMTV-Wnt1 murine mammary stem cell viability.

  DOI：

  10.1021/jm2011436

文献信息

• Induction of apoptosis in cancer cells
  申请人：——

  公开号：US20030176506A1

  公开（公告）日：2003-09-18

  The present invention provides compounds that are inducers or inhibitors of apoptosis or apoptosis preceded by cell-cycle arrest. In addition, the present invention provides pharmaceutical compositions and methods for treating mammals with leukemia or other forms of cancer or for treating disease conditions caused by apoptosis of cells.

  本发明提供了诱导或抑制凋亡或在细胞周期停滞之前发生的凋亡的化合物。此外，本发明提供了用于治疗患有白血病或其他形式癌症的哺乳动物或治疗由细胞凋亡引起的疾病状况的药物组合物和方法。
• INDUCTION OF APOPTOSIS IN CANCER CELLS
  申请人：The Burnham Institute

  公开号：EP1456165A1

  公开（公告）日：2004-09-15
• US7053071B2
  申请人：——

  公开号：US7053071B2

  公开（公告）日：2006-05-30
• USRE42700E1
  申请人：——

  公开号：USRE42700E1

  公开（公告）日：2011-09-13
• [EN] INDUCTION OF APOPTOSIS IN CANCER CELLS<br/>[FR] INDUCTION DE L'APOPTOSE DANS LES CELLULES CANCEREUSES
  申请人：BURNHAM INST

  公开号：WO2003048101A1

  公开（公告）日：2003-06-12

  The present invention provides compounds that are inducers or inhibitors of apoptosis or apoptosis preceded by cell-cycle arrest. In addition, the present invention provides pharmaceutical compositions and methods for treating mammals with leukemia or other forms of cancer or for treating disease conditions caused by apoptosis of cells.