3-(2-(dibenzylamino)-2-oxoacetyl)-1H-indol-4-yl acetate | 77872-23-2

• 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: 3-(2-(dibenzylamino)-2-oxoacetyl)-1H-indol-4-yl acetate
• 英文别名: [3-[2-(dibenzylamino)-2-oxoacetyl]-1H-indol-4-yl] acetate
• CAS: 77872-23-2
• 化学式: C₂₆H₂₂N₂O₄
• 分子量: 426.472
• InChiKey: ZYCLFZTZPIBGLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-(dibenzylamino)-2-oxoacetyl)-1H-indol-4-yl acetate 在 盐酸 、 lithium aluminium tetrahydride 、 正丁基锂 、 20% palladium hydroxide-activated charcoal 、 氢气 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 、 甲醇 、 乙醚 、 水 为溶剂， -78.0~78.0 ℃ 、101.33 kPa 条件下， 反应 79.25h， 生成 norbaeocystin
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin

  摘要：

  A general synthetic method was developed to access known tryptamine natural products present in psilocybin-producing mushrooms. In vitro and in vivo experiments were then conducted to inform speculations on the psychoactive properties, or lack thereof, of the natural products. In animal models, psychedelic activity by baeocystin alone was not evident using the mouse head twitch response assay, despite its putative dephosphorylated metabolite, norpsilocin, possessing potent agonist activity at the 5-HT2A receptor.

  DOI：

  10.1021/acs.jnatprod.9b01061
• 作为产物：
  描述：

  4-乙酰氧基吲哚 以 四氢呋喃 、 甲基叔丁基醚 为溶剂， 反应 3.5h， 生成 3-(2-(dibenzylamino)-2-oxoacetyl)-1H-indol-4-yl acetate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin

  摘要：

  A general synthetic method was developed to access known tryptamine natural products present in psilocybin-producing mushrooms. In vitro and in vivo experiments were then conducted to inform speculations on the psychoactive properties, or lack thereof, of the natural products. In animal models, psychedelic activity by baeocystin alone was not evident using the mouse head twitch response assay, despite its putative dephosphorylated metabolite, norpsilocin, possessing potent agonist activity at the 5-HT2A receptor.

  DOI：

  10.1021/acs.jnatprod.9b01061

文献信息

• Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-(<i>N</i>-methyl-<i>N</i>-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols
  作者：David B. Repke、Wilfred J. Ferguson、Dallas K. Bates

  DOI：10.1002/jhet.5570180131

  日期：1981.1

  Structural alteration of the Nb-substituents of psilocin (3-[2-dimethylamino)ethyl]indol-4-ol) (12a) has led to a number of compounds containing known pharmacophoric groups. Further, it is hoped that the subtle changes in the nature of these substituents may lead to a clearer understanding of the structure-activity relationships of the 4-hydroxytryptamine hallucinogens.

  psilocin（3- [2-二甲基氨基）乙基]吲哚-4-醇（12a）的N b-取代基的结构改变导致许多化合物含有已知的药效基团。此外，希望这些取代基的性质的细微变化可以导致对4-羟基色胺致幻剂的结构-活性关系的更清楚的理解。