2-(3-Pentyl-3H-diazirin-3-yl)-ethanol | 245440-54-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环化合物
• 英文名称: 2-(3-Pentyl-3H-diazirin-3-yl)-ethanol
• 英文别名: 3H-Diazirine-3-ethanol, 3-pentyl-；2-(3-pentyldiazirin-3-yl)ethanol
• CAS: 245440-54-4
• 化学式: C₈H₁₆N₂O
• 分子量: 156.228
• InChiKey: UFRORYJOZHLIFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(tert-butylmethylsilyloxy)octan-3-one 在 盐酸 、 氨 、 碘 、 三乙胺 、 hydroxylamine-O-sulfonic acid 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 2-(3-Pentyl-3H-diazirin-3-yl)-ethanol
  参考文献：
  名称：

  Synthesis and Properties of 3-(2-Hydroxyethyl)-3-n-pentyldiazirine, a Photoactivable General Anesthetic

  摘要：

  To overcome the difficulties of locating the molecular sites of general anesthetic action, we synthesized a novel photoactivable general anesthetic, 3-(2-hydroxyethyl)-3-n-pentyldiazirine (3-diazirinyloctanol), which anesthetized tadpoles with an ED50 of 160 mu M. Subanesthetic concentrations of 3-diazirinyloctanol enhanced GABA-induced currents in GABA(A) receptors, an effect that has been implicated in general anesthetic action. It also enhanced [H-3]muscimol binding to this receptor. In muscle nicotinic acetylcholine receptors (nAcChoR), it inhibited the response to acetylcholine with an IC50 of 33 mu M. 3-Diazirinyloctanol's pharmacological actions were comparable to those of octanol. 3-(2-Hydroxyethyl)-3-[4,5-H-3(2)]-n-pentyldiazirine photoincorporated into Torpedo nAcChoR-rich membranes mainly in the alpha subunit with 70% being in a proteolytic fragment containing the M4 transmembrane segment. Agonist enhanced the photolabeling 10-fold in a fragment containing the M1, M2, and M3 transmembrane segments. Thus, 3-diazirinyloctanol is a novel general anesthetic that acts on, and can be photoincorporated into, postsynaptic receptors.

  DOI：

  10.1021/jm9806300