1-(5-hydroxy-3-methyl-1H-indol-2-yl)ethanone | 937177-46-3

• 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: 1-(5-hydroxy-3-methyl-1H-indol-2-yl)ethanone
• CAS: 937177-46-3
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: AOKCOTWEOOARRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5-hydroxy-3-methyl-1H-indol-2-yl)ethanone 在 4-二甲氨基吡啶 、 (R)-2-methyl-CBS-oxazaboroline 、 二苯基磷酸 、 sodium hydride 、 三乙基硼氢化锂 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 potassium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成
  参考文献：
  名称：

  Estrogen receptor ligands. Part 16: 2-Aryl indoles as highly subtype selective ligands for ERα

  摘要：

  A novel class of indole ligands for estrogen receptor alpha have been discovered which exhibit potent affinity and high selectivity. Substitution of the bazedoxifene skeleton to the linker present in the HTS lead 1a provided 22b which was found to be 130-fold alpha-selective and acted as an antagonist of estradiol activity in uterine tissue and MCF-7 cancer cells.

  DOI：

  10.1016/j.bmcl.2007.01.054
• 作为产物：
  描述：

  1-(5-Methoxy-3-methyl-1H-indol-2-yl)-ethanone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以74%的产率得到1-(5-hydroxy-3-methyl-1H-indol-2-yl)ethanone
  参考文献：
  名称：

  Estrogen receptor ligands. Part 16: 2-Aryl indoles as highly subtype selective ligands for ERα

  摘要：

  A novel class of indole ligands for estrogen receptor alpha have been discovered which exhibit potent affinity and high selectivity. Substitution of the bazedoxifene skeleton to the linker present in the HTS lead 1a provided 22b which was found to be 130-fold alpha-selective and acted as an antagonist of estradiol activity in uterine tissue and MCF-7 cancer cells.

  DOI：

  10.1016/j.bmcl.2007.01.054

文献信息

• Estrogen receptor ligands. Part 16: 2-Aryl indoles as highly subtype selective ligands for ERα
  作者：Kevin D. Dykstra、Liangqin Guo、Elizabeth T. Birzin、Wanda Chan、Yi Tien Yang、Edward C. Hayes、Carolyn A. DaSilva、Lee-Yuh Pai、Ralph T. Mosley、Bryan Kraker、Paula M.D. Fitzgerald、Frank DiNinno、Susan P. Rohrer、James M. Schaeffer、Milton L. Hammond

  DOI：10.1016/j.bmcl.2007.01.054

  日期：2007.4

  A novel class of indole ligands for estrogen receptor alpha have been discovered which exhibit potent affinity and high selectivity. Substitution of the bazedoxifene skeleton to the linker present in the HTS lead 1a provided 22b which was found to be 130-fold alpha-selective and acted as an antagonist of estradiol activity in uterine tissue and MCF-7 cancer cells.