N-methyl-2-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]ethanamine | 1242978-56-8

• 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: N-methyl-2-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]ethanamine
• 英文别名: N-methyl-2-(1,1-dimethylallyl)tryptamine
• CAS: 1242978-56-8
• 化学式: C₁₆H₂₂N₂
• 分子量: 242.364
• InChiKey: ASNSVGRCYSMIIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-methyl-2-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]ethanamine 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 以50%的产率得到N-methyl-2-(1,1-dimethylallyl)tryptamine hydrochloride
  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：

  N¹⁰-BOC-N¹⁰-methyltryptamine 在 次氯酸叔丁酯 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-methyl-2-[2-(2-methylbut-3-en-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

文献信息

• Study on the NBS-Induced Rearrangement of 2-tert-Prenyltryptamines
  作者：Thomas Lindel、Santosh Adla、Gregor Golz、Peter Jones

  DOI：10.1055/s-0029-1218811

  日期：2010.7

  2-tert-prenyltryptamines with N-bromosuccinimide gives clean access to the marine natural product flustramine C and analogues with the tert-prenyl group shifted to the 3a-position of the resulting pyrrolo[2,3-b]indole (70-80%). Dihydroflustramine C was obtained by DIBAL-H reduction of flustramine C. Bromination or N-methylation of the indole moiety does not influence the course of the rearrangement. alkaloids - flustramines

  用N-溴丁二酰亚胺处理2-叔戊烯基色胺可以使海洋天然产物氟他胺C和叔戊烯基移至所得吡咯并[2,3- b ]吲哚的3a-位的类似物（70- 80％）。通过DIBAL-H还原氟雌胺C获得二氢氟雌胺C。吲哚部分的溴化或N-甲基化不影响重排的过程。 生物碱-氟他胺-吲哚-海洋天然产物-异戊二烯迁移