(S)-1-(1H-benzo[d]imidazol-2-yl)-2-(1H-indol-3-yl)-ethanamine | 59592-36-8

• 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: (S)-1-(1H-benzo[d]imidazol-2-yl)-2-(1H-indol-3-yl)-ethanamine
• 英文别名: α-(2-benzimidazolyl)-β-(3-indolyl)ethylamine；(1S)-1-(1H-benzimidazol-2-yl)-2-(1H-indol-3-yl)ethanamine
• CAS: 59592-36-8
• 化学式: C₁₇H₁₆N₄
• 分子量: 276.341
• InChiKey: ZWFNPSCBOVCVTB-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70.5
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-(1H-benzo[d]imidazol-2-yl)-2-(1H-indol-3-yl)-ethanamine 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 (2R)-N-[(1S)-1-(1H-benzimidazol-2-yl)-2-(1H-indol-3-yl)ethyl]-N'-hydroxy-2-(2-methylpropyl)butanediamide
  参考文献：
  名称：

  Design, synthesis, activity, and structure of a novel class of matrix metalloproteinase inhibitors containing a heterocyclic P2′-P3′ amide bond isostere

  摘要：

  A novel series of hydroxamate-based inhibitors of matrix metalloproteinases containing benzimidazole and imidazole heterocycles as amide bond isosteres have been prepared. Potent inhibition (in the low nanomolar range) and selectivity (> 100-fold) can be attained with inhibitors containing only one amide bond. X-ray crystal structures of matrilysin (MMP-7) with two different inhibitors bound confirm that imidazole is an excellent amide bond isostere. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00283-1
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 0.33h， 生成 (S)-1-(1H-benzo[d]imidazol-2-yl)-2-(1H-indol-3-yl)-ethanamine
  参考文献：
  名称：

  Design, synthesis, activity, and structure of a novel class of matrix metalloproteinase inhibitors containing a heterocyclic P2′-P3′ amide bond isostere

  摘要：

  A novel series of hydroxamate-based inhibitors of matrix metalloproteinases containing benzimidazole and imidazole heterocycles as amide bond isosteres have been prepared. Potent inhibition (in the low nanomolar range) and selectivity (> 100-fold) can be attained with inhibitors containing only one amide bond. X-ray crystal structures of matrilysin (MMP-7) with two different inhibitors bound confirm that imidazole is an excellent amide bond isostere. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00283-1

文献信息

• Synthesis of Benzimidazoles from Amino Acids with Solvent-free Melting Method
  作者：Ren-Hong Chen、Jin-Feng Xiong、Pai Peng、Guang-Zhen Mo、Xing-San Tang、Zhao-Yang Wang、Xiu-Fang Wang

  DOI：10.14233/ajchem.2014.16438

  日期：——

  By using low cost and readily available amino acids as the synthetic blocks, a series of 2-aminomethyl-benzimidazole are synthesized with solvent-free melting method. While the condensation of aspartic acid (or asparagine) with o-diaminobenzene gives the fluorescent bisbenzimidazole product without amino group via the further deamination reaction in the melting reaction system. The condensation reactions between most amino acids and o-diaminobenzenes exhibits higher yields of 58 to 86 % (mostly over 66 %), shorter reaction time (5 h) than that previously reported and better tolerance for different functional groups in amino acids. The structures of twenty benzimidazoles with multifunctional groups, including thirteen new compounds, are systematically characterized with FTIR, 1H NMR, 13C NMR, MS and elemental analysis. These investigations are beneficial to the further researches on their applications in biochemistry, coordination chemistry and organic synthesis intermediates.

  利用低成本且易获取的氨基酸作为合成模块，通过无溶剂熔融法合成了一系列2-氨基甲基苯并咪唑。将天冬氨酸（或天冬酰胺）与邻二氨基苯缩合，在熔融反应体系中通过进一步的脱氨基反应得到了无氨基的发光双苯并咪唑产物。大多数氨基酸与邻二氨基苯的缩合反应表现出更高的产率（58%至86%，大多超过66%），反应时间更短（5小时），并且对氨基酸中的不同官能团具有更好的耐受性。通过FTIR、1H NMR、13C NMR、MS和元素分析系统地表征了含有多官能团的二十种苯并咪唑的结构，其中包括十三种新化合物。这些研究有利于进一步探索它们在生物化学、配位化学和有机合成中间体中的应用。
• Nuclear Magnetic Resonance Reveals Molecular Species in Carbon Nanodot Samples Disclosing Flaws
  作者：Beatrice Bartolomei、Andrea Bogo、Francesco Amato、Giulio Ragazzon、Maurizio Prato

  DOI：10.1002/anie.202200038

  日期：2022.5.9

  The purification of carbon nanodots is a critical aspect in their preparation, especially for syntheses involving molecular precursors. Indeed, the presence of organic molecules in the final sample can lead to mistaken conclusions regarding their properties. In this work, NMR is proven to be an essential technique to verify the purification of carbon nanodots, thanks to its ability to disclose molecular

  碳纳米点的纯化是其制备的一个关键方面，特别是对于涉及分子前体的合成。事实上，最终样品中有机分子的存在可能会导致对其特性得出错误的结论。在这项工作中，核磁共振被证明是验证碳纳米点纯化的一项重要技术，因为它能够揭示分子种类。