ethyl (E)-3-[6-(1-adamantyl)-7-hydroxy-9H-carbazol-2-yl]propenoate | 1352042-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl (E)-3-[6-(1-adamantyl)-7-hydroxy-9H-carbazol-2-yl]propenoate
• 英文别名: ethyl (E)-3-[6-(1-adamantyl)-7-hydroxy-9H-carbazol-2-yl]prop-2-enoate
• CAS: 1352042-82-0
• 化学式: C₂₇H₂₉NO₃
• 分子量: 415.532
• InChiKey: QRBXIDODGTUFIG-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (E)-3-[6-(1-adamantyl)-7-hydroxy-9H-carbazol-2-yl]propenoate 在 lithium hydroxide monohydrate 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 23.0h， 以38%的产率得到(E)-3-[8-(1-adamantyl)-7-hydroxy-9H-carbazol-2-yl]propenoic 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
• 作为产物：
  描述：

  4-溴-3-硝基苯甲醛 在 四(三苯基膦)钯 、 三溴化硼 、 sodium carbonate 、 三苯基膦 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 邻二氯苯 、 甲苯 为溶剂， 反应 55.8h， 生成 ethyl (E)-3-[6-(1-adamantyl)-7-hydroxy-9H-carbazol-2-yl]propenoate
  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

• Analogues of Orphan Nuclear Receptor Small Heterodimer Partner Ligand and Apoptosis Inducer (<i>E</i>)-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
  作者：Zebin Xia、Ricardo G. Correa、Jayanta K. Das、Lulu Farhana、David J. Castro、Jinghua Yu、Robert G. Oshima、Joseph A. Fontana、John C. Reed、Marcia I. Dawson

  DOI：10.1021/jm2011436

  日期：2012.1.12

  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.