2-(1H-indol-3-yl)-N-(naphthalen-1-ylmethylene)ethanamine | 16841-85-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1H-indol-3-yl)-N-(naphthalen-1-ylmethylene)ethanamine
• 英文别名: N-(1-Naphthyl-methylen)-tryptamin；(2-indol-3-yl-ethyl)-naphthalen-1-ylmethylene-amine；N-(1-Naphthalenylmethylene)-1H-indole-3-ethanamine；N-[2-(1H-indol-3-yl)ethyl]-1-naphthalen-1-ylmethanimine
• CAS: 16841-85-3
• 化学式: C₂₁H₁₈N₂
• 分子量: 298.387
• InChiKey: REALGTUKPSGRLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(1H-indol-3-yl)-N-(naphthalen-1-ylmethylene)ethanamine 在 sodium tetrahydroborate 、 (S)-6,6'-di(naphthalen-1-yl)-1,1'-spirobiindane-7,7'-diyl phosphate 、 10% Pd(OH)₂ on C 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 苯 为溶剂， 反应 11.08h， 生成 (S)-3-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)propan-1-ol
  参考文献：
  名称：

  SPINOL-磷酸催化的高对映选择性Pictet-Spengler反应

  摘要：

  手性SPINOL-磷酸是N b -α-萘甲基甲基色胺与一系列脂族和芳族醛的不对称Pictet-Spengler反应的高度对映选择性催化剂，可提供具有优异收率和ee值的旋光四氢-β-咔啉。当前协议已应用于（-）-甜菜碱的不对称总合成中。

  DOI：

  10.1002/chem.201103207
• 作为产物：
  描述：

  色胺 、 1-萘甲醛 以 甲醇 为溶剂， 反应 36.0h， 生成 2-(1H-indol-3-yl)-N-(naphthalen-1-ylmethylene)ethanamine
  参考文献：
  名称：

  SPINOL-磷酸催化的高对映选择性Pictet-Spengler反应

  摘要：

  手性SPINOL-磷酸是N b -α-萘甲基甲基色胺与一系列脂族和芳族醛的不对称Pictet-Spengler反应的高度对映选择性催化剂，可提供具有优异收率和ee值的旋光四氢-β-咔啉。当前协议已应用于（-）-甜菜碱的不对称总合成中。

  DOI：

  10.1002/chem.201103207

文献信息

• Scalable methodologies for the synthesis of novel unsymmetrically-substituted secondary amines
  作者：Gheorghe Roman

  DOI：10.2298/jsc110408173r

  日期：——

  Fast, easy, and scalable methodologies for the synthesis of unsym- metrically substituted secondary amines containing naphthalene, indole, pyri- dine and imidazole moieties through reductive amination were explored. The investigated operating procedures were successful on a 50- to 30-mmol scale, and present a high potential for up-scaling.

  探索了快速，简便，可扩展的方法，用于通过还原胺化合成包含萘，吲哚，吡啶和咪唑部分的不对称取代的仲胺。所研究的操作程序在50至30 mmol的规模上是成功的，并且具有扩大规模的巨大潜力。
• Schiff bases of tryptamine as potent inhibitors of nucleoside triphosphate diphosphohydrolases (NTPDases): Structure-activity relationship
  作者：Kanwal、Khalid Mohammed Khan、Uzma Salar、Saira Afzal、Abdul Wadood、Muhammad Taha、Shahnaz Perveen、Huma Khan、Joanna Lecka、Jean Sévigny、Jamshed Iqbal

  DOI：10.1016/j.bioorg.2018.10.046

  日期：2019.2

  Overexpression of NTPDases leads to a number of pathological situations such as thrombosis, and cancer. Thus, effective inhibitors are required to combat these pathological situations. Different classes of NTPDase inhibitors are reported so far including nucleotides and their derivatives, sulfonated dyes such as reactive blue 2, suramin and its derivatives, and polyoxomatalates (POMs). Suramin is a well-known and potent NTPDase inhibitor, nonetheless, a range of side effects are also associated with it. Reactive blue 2 also had non-specific side effects that become apparent at high concentrations. In addition, most of the NTPDase inhibitors are high molecular weight compounds, always required tedious chemical steps to synthesize. Hence, there is still need to explore novel, low molecular weight, easy to synthesize, and potent NTPDase inhibitors.Keeping in mind the known NTPDase inhibitors with imine functionality and nitrogen heterocycles, Schiff bases of tryptamine, 1-26, were synthesized and characterized by spectroscopic techniques such as EI-MS, HREI-MS, H-1-, and C-13 NMR. All the synthetic compounds were evaluated for the inhibitory avidity against activities of three major isoforms of NTPDases: NTPDase-1, NTPDase-3, and NTPDase-8. Cumulatively, eighteen compounds were found to show potent inhibition (Ki = 0.0200-0.350 mu M) of NTPDase-1, twelve (Ki = 0.071-1.060 mu M) of NTPDase-3, and fifteen compounds inhibited (Ki = 0.0700-4.03 mu M) NTPDase-8 activity. As a comparison, the Kis of the standard inhibitor suramin were 1.260 +/- 0.007, 6.39 +/- 0.89 and 1.180 +/- 0.002 mu M, respectively. Kinetic studies were performed on lead compounds (6, 5, and 21) with human (h-) NTPDase-1, -3, and -8, and Lineweaver-Burk plot analysis showed that they were all competitive inhibitors. In silico study was conducted on compound 6 that showed the highest level of inhibition of NTPDase-1 to understand the binding mode in the active site of the enzyme.
• Highly Enantioselective Pictet-Spengler Reaction Catalyzed by SPINOL-Phosphoric Acids
  作者：Dan Huang、Fangxi Xu、Xufeng Lin、Yanguang Wang

  DOI：10.1002/chem.201103207

  日期：2012.3.12

  enantioselective catalysts for the asymmetric Pictet–Spengler reaction of Nb‐α‐naphthylmethyl tryptamines with a series of aliphatic and aromatic aldehydes, affording optically active tetrahydro‐β‐carbolines in excellent yields and ee values. The current protocol has been applied in the asymmetric total synthesis of (−)‐harmicine.

  手性SPINOL-磷酸是N b -α-萘甲基甲基色胺与一系列脂族和芳族醛的不对称Pictet-Spengler反应的高度对映选择性催化剂，可提供具有优异收率和ee值的旋光四氢-β-咔啉。当前协议已应用于（-）-甜菜碱的不对称总合成中。