tert-butyl N-methyl-N-[2-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]ethyl]carbamate | 1338383-27-9

• 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: tert-butyl N-methyl-N-[2-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]ethyl]carbamate
• CAS: 1338383-27-9
• 化学式: C₂₁H₃₀N₂O₂
• 分子量: 342.481
• InChiKey: HYIKMIWGDDJQFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl N-methyl-N-[2-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]ethyl]carbamate 在 palladium 10% on activated carbon 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 N-methyl-2-[2-(2-methylbutan-2-yl)-1H-indol-3-yl]ethanamine
  参考文献：
  名称：

  Deconstruction of the α4β2 Nicotinic Acetylcholine Receptor Positive Allosteric Modulator Desformylflustrabromine

  摘要：

  Desformylflustrabromine (dFBr; 1), perhaps the first selective positive allosteric modulator of alpha 4 beta 2 neuronal nicotinic acetylcholine (nACh) receptors, was deconstructed to determine which structural features contribute to its actions on receptors expressed in Xenopus ooycytes using two-electrode voltage clamp techniques. Although the intact structure of 1 was found to be optimal, several deconstructed analogs retained activity. Neither the 6-bromo substituent nor the entire 2-position chain is required for activity. In particular, reduction of the olefinic side chain of 1, as seen with 6, not only resulted in retention of activity/potency but in enhanced selectivity for alpha 4 beta 2 versus alpha 7 nACh receptors. Pharmacophoric features for the allosteric modulation of alpha 4 beta 2 nACh receptors by 1 were identified.

  DOI：

  10.1021/jm200834x
• 作为产物：
  描述：

  prenyl 9-BBN 、 N¹⁰-BOC-N¹⁰-methyltryptamine 在 次氯酸叔丁酯 、 三乙胺 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以40%的产率得到tert-butyl N-methyl-N-[2-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]ethyl]carbamate
  参考文献：
  名称：

  Deconstruction of the α4β2 Nicotinic Acetylcholine Receptor Positive Allosteric Modulator Desformylflustrabromine

  摘要：

  Desformylflustrabromine (dFBr; 1), perhaps the first selective positive allosteric modulator of alpha 4 beta 2 neuronal nicotinic acetylcholine (nACh) receptors, was deconstructed to determine which structural features contribute to its actions on receptors expressed in Xenopus ooycytes using two-electrode voltage clamp techniques. Although the intact structure of 1 was found to be optimal, several deconstructed analogs retained activity. Neither the 6-bromo substituent nor the entire 2-position chain is required for activity. In particular, reduction of the olefinic side chain of 1, as seen with 6, not only resulted in retention of activity/potency but in enhanced selectivity for alpha 4 beta 2 versus alpha 7 nACh receptors. Pharmacophoric features for the allosteric modulation of alpha 4 beta 2 nACh receptors by 1 were identified.

  DOI：

  10.1021/jm200834x

文献信息

• Deconstruction of the α4β2 Nicotinic Acetylcholine Receptor Positive Allosteric Modulator Desformylflustrabromine
  作者：Nadezhda German、Jin-Sung Kim、Atul Jain、Malgorzata Dukat、Anshul Pandya、Yilong Ma、Maegan Weltzin、Marvin K. Schulte、Richard A. Glennon

  DOI：10.1021/jm200834x

  日期：2011.10.27

  Desformylflustrabromine (dFBr; 1), perhaps the first selective positive allosteric modulator of alpha 4 beta 2 neuronal nicotinic acetylcholine (nACh) receptors, was deconstructed to determine which structural features contribute to its actions on receptors expressed in Xenopus ooycytes using two-electrode voltage clamp techniques. Although the intact structure of 1 was found to be optimal, several deconstructed analogs retained activity. Neither the 6-bromo substituent nor the entire 2-position chain is required for activity. In particular, reduction of the olefinic side chain of 1, as seen with 6, not only resulted in retention of activity/potency but in enhanced selectivity for alpha 4 beta 2 versus alpha 7 nACh receptors. Pharmacophoric features for the allosteric modulation of alpha 4 beta 2 nACh receptors by 1 were identified.