N-<2-<2-trimethylsilyl-1H-pyrrolo<3,2-c>pyridin-3-yl>ethyl>acetamide | 183208-19-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-<2-<2-trimethylsilyl-1H-pyrrolo<3,2-c>pyridin-3-yl>ethyl>acetamide
• 英文别名: 3-(N-acetylaminoethyl)-2-trimethylsilyl-1H-pyrrolo[3,2-c]pyridine；N-[2-(2-trimethylsilyl-1H-pyrrolo[3,2-c]pyridin-3-yl)ethyl]acetamide
• CAS: 183208-19-7
• 化学式: C₁₄H₂₁N₃OSi
• 分子量: 275.426
• InChiKey: SLQPHGSTZFBWPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-<2-<2-trimethylsilyl-1H-pyrrolo<3,2-c>pyridin-3-yl>ethyl>acetamide 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 sodium hydroxide 、 2,6-二叔丁基-4-甲基苯酚 、 一氯化碘 、 lithium chloride 作用下， 以 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-aminoethyl-2-ethyl-1H-pyrrolo[3,2-c]pyridine
  参考文献：
  名称：

  5-ZATRYPTAMINE ANALOGS AS h5-HT6 SEROTONIN RECEPTOR LIGANDS

  摘要：

  5-Aza analogs were prepared of several tryptamine derivatives and a skatole derivative known to bind at human 5-HT6 receptors and evaluated to determine if they bind in a manner similar to their indolic analogs. In general, the azatryptamines did not behave exactly like their tryptamine counterparts, but the behavior of NI-benzenesulfonyl analogs was reminiscent of the known arylsulfonyltryptamines. For example, N-1-(4-aminobenzenesulfonyl)-5-azaskatole (18; K-i = 41 nM) displayed an affinity comparable to N-1-(4-aminobenzenesulfonyl)skatole.

  DOI：

  10.1007/s00044-004-0121-8
• 作为产物：
  描述：

  4-(三甲基甲硅烷基)丁-3-炔-1-胺 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-<2-<2-trimethylsilyl-1H-pyrrolo<3,2-c>pyridin-3-yl>ethyl>acetamide
  参考文献：
  名称：

  5-ZATRYPTAMINE ANALOGS AS h5-HT6 SEROTONIN RECEPTOR LIGANDS

  摘要：

  5-Aza analogs were prepared of several tryptamine derivatives and a skatole derivative known to bind at human 5-HT6 receptors and evaluated to determine if they bind in a manner similar to their indolic analogs. In general, the azatryptamines did not behave exactly like their tryptamine counterparts, but the behavior of NI-benzenesulfonyl analogs was reminiscent of the known arylsulfonyltryptamines. For example, N-1-(4-aminobenzenesulfonyl)-5-azaskatole (18; K-i = 41 nM) displayed an affinity comparable to N-1-(4-aminobenzenesulfonyl)skatole.

  DOI：

  10.1007/s00044-004-0121-8

文献信息

• Aza-Tryptamine Substrates in Monoterpene Indole Alkaloid Biosynthesis
  作者：Hyang-Yeol Lee、Nancy Yerkes、Sarah E. O'Connor

  DOI：10.1016/j.chembiol.2009.11.016

  日期：2009.12

  as the starting substrate for a variety of alkaloid biosynthetic pathways, by replacing the indole with one of four aza-indole isomers. We show that two aza-tryptamine substrates can be successfully incorporated into the products of the monoterpene indole alkaloid pathway inCatharanthus roseus. Use of unnatural heterocycles in precursor-directed biosynthesis, in both microbial and plant natural product pathways

  通过引入新的起始材料，可以劫持生物合成途径以产生新的化合物。在这里，我们通过用四种氮杂吲哚异构体之一替换吲哚来改变色胺，色胺是各种生物碱生物合成途径的起始底物。我们表明两种氮杂色胺底物可以成功地掺入长春花中单萜吲哚生物碱途径的产物中。非天然杂环在微生物和植物天然产物途径中的前体导向生物合成中的使用尚未得到广泛证明，并且先前未报道过成功掺入含有氮杂吲哚官能团的起始底物类似物。
• Synthesis of New Melatoninergic Ligands Including Azaindole Moiety
  作者：Marie-Claude Viaud-Massuard、Daniel Mazéas、Gérald Guillaumet

  DOI：10.3987/com-98-s(h)111

  日期：——
• 5-ZATRYPTAMINE ANALOGS AS h5-HT6 SEROTONIN RECEPTOR LIGANDS
  作者：Manik Pullagurla、Małgorzata Dukat、Bryan L. Roth、Vincent Setola、Richard A. Glennon

  DOI：10.1007/s00044-004-0121-8

  日期：2005.1

  5-Aza analogs were prepared of several tryptamine derivatives and a skatole derivative known to bind at human 5-HT6 receptors and evaluated to determine if they bind in a manner similar to their indolic analogs. In general, the azatryptamines did not behave exactly like their tryptamine counterparts, but the behavior of NI-benzenesulfonyl analogs was reminiscent of the known arylsulfonyltryptamines. For example, N-1-(4-aminobenzenesulfonyl)-5-azaskatole (18; K-i = 41 nM) displayed an affinity comparable to N-1-(4-aminobenzenesulfonyl)skatole.