N1,N10-dimethyl-N10-Boc-tryptamine | 1383168-19-1

• 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: N1,N10-dimethyl-N10-Boc-tryptamine
• CAS: 1383168-19-1
• 化学式: C₁₇H₂₄N₂O₂
• 分子量: 288.39
• InChiKey: SCOUWKYZDZWVOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  34.47
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N1,N10-dimethyl-N10-Boc-tryptamine 在 sodium cyanoborohydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 N,N-dimethyl-2-(1-methyl-1H-indol-3-yl)ethan-1-amine
  参考文献：
  名称：

  Identification of Psychoplastogenic N,N-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure–Activity Relationship Studies

  摘要：

  Ketamine, N,N-dimethyltryptamine (DMT), and other psychoplastogens possess enormous potential as neurotherapeutics due to their ability to potently promote neuronal growth. Here, we report the first-ever structure activity relationship study with the explicit goal of identifying novel psychoplastogens. We have discovered several key features of the psychoplastogenic pharmacophore and used this information to develop N,N-dimethylaminoisotryptamine (isoDMT) psychoplastogens that are easier to synthesize, have improved physicochemical properties, and possess reduced hallucinogenic potential as compared to their DMT counterparts.

  DOI：

  10.1021/acs.jmedchem.9b01404
• 作为产物：
  描述：

  [2-(1H-吲哚-3-基)乙基]氨基甲酸叔丁酯 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 N1,N10-dimethyl-N10-Boc-tryptamine
  参考文献：
  名称：

  Identification of Psychoplastogenic N,N-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure–Activity Relationship Studies

  摘要：

  Ketamine, N,N-dimethyltryptamine (DMT), and other psychoplastogens possess enormous potential as neurotherapeutics due to their ability to potently promote neuronal growth. Here, we report the first-ever structure activity relationship study with the explicit goal of identifying novel psychoplastogens. We have discovered several key features of the psychoplastogenic pharmacophore and used this information to develop N,N-dimethylaminoisotryptamine (isoDMT) psychoplastogens that are easier to synthesize, have improved physicochemical properties, and possess reduced hallucinogenic potential as compared to their DMT counterparts.

  DOI：

  10.1021/acs.jmedchem.9b01404

文献信息

• Copper-Catalyzed Selective Electron Transfer Enables Switchable Divergent Synthesis of 3-Functionalized Oxindoles
  作者：Shu-Yun Jiang、Jun Shi、Wei Wang、Yan-Zheng Sun、Wei Wu、Jun-Rong Song、Xiaoyan Yang、Ge-Fei Hao、Wei-Dong Pan、Hai Ren

  DOI：10.1021/acscatal.2c05881

  日期：2023.3.3

  this time-consuming and complex task produces a single type of product via two-electron oxidation using stoichiometric chemical oxidants. Herein, we report a unified and efficient copper-catalyzed selective single-electron transfer strategy for three oxidation reactions of 3-substituted indoles using air (O2) as the terminal oxidant, providing a streamlined and practical synthetic approach to access 3-hydroxyl-

  3-取代吲哚的氧化重排是合成 2-羟吲哚支架的基本有机转化。然而，这项耗时且复杂的任务使用化学计量化学氧化剂通过双电子氧化产生单一类型的产品。在此，我们报告了一种统一且高效的铜催化选择性单电子转移策略，用于使用空气 (O 2 ) 作为末端氧化剂的 3-取代吲哚的三种氧化反应，提供了一种简化且实用的合成方法来获得 3-羟基- , 3-烷氧基-, 和 3-hygrogenous-2-oxindoles通过3-自由基-2-羟基二氢吲哚中间体。这种铜催化方案在生物 3-功能化羟吲哚衍生物的模块化合成中表现出高化学选择性、良好的官能团耐受性和广泛的应用潜力。
• Synthesis and evaluation of N1-alkylindole-3-ylalkylammonium compounds as nicotinic acetylcholine receptor ligands
  作者：Edwin G. Pérez、Bruce K. Cassels、Christoph Eibl、Daniela Gündisch

  DOI：10.1016/j.bmc.2012.04.050

  日期：2012.6

  In this study thirty-three novel indole derivatives were designed and synthesized based on the structure of deformylflustrabromine B (1), a metabolite isolated from the marine bryozoan Flustra foliacea L. The syntheses were carried out using standard methodologies and in good yields. The molecules were tested for their affinities for the alpha 4 beta 2*, alpha 3 beta 4*, alpha 7* and (alpha 1)(2)beta 1 gamma delta nicotinic acetylcholine receptor (nAChR) sub-types. Binding assays showed that, among these ligands, compound 7c exhibited the highest affinity with K-i = 136.1, 93.9 and 862.4 nM for the alpha 4 beta 2*, alpha 3 beta 4*, and alpha 7* nAChRs subtypes, respectively. These results indicated that the indole core might be a useful scaffold for the development of new potent and selective nAChR ligands. (C) 2012 Elsevier Ltd. All rights reserved.