1-(furan-2-ylmethyl)-1H-indole | 605663-21-6

• 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: 1-(furan-2-ylmethyl)-1H-indole
• 英文别名: 1-(Furan-2-ylmethyl)indole
• CAS: 605663-21-6
• 化学式: C₁₃H₁₁NO
• 分子量: 197.236
• InChiKey: ZUXLFJSRSKDSOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  18.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(furan-2-ylmethyl)-1H-indole 在 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.0h， 生成 2-[1-(furan-2-ylmethyl)indol-3-yl]-2-oxo-N-quinolin-6-ylacetamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of N-Heterocyclic Indolyl Glyoxylamides as Orally Active Anticancer Agents

  摘要：

  A series of N-heterocyclic indolyl glyoxylamides were synthesized and evaluated for in vitro and in vivo anticancer activities. They exhibited a broad spectrum of anticancer activity not only in murine leukemic cancer cells but also in human gastric, breast, and uterus cancer cells as well as their multidrug resistant sublines with a wide range of IC50 values. They also induced apoptosis and caused DNA fragmentation in human gastric cancer cells. Among the compounds studied, 7 showed the most potent activity of growth inhibition (IC50 = 17-1711 nM) in several human cancer cells. Given orally, compounds 7 and 13 dose-dependently prolonged the survival of animals inoculated with P388 leukemic cancer cells. N-Heterocyclic indolyl glyoxylamides may be useful as orally active chemotherapeutic agents against cancer and refractory cancerous diseases of multidrug resistance phenotype.

  DOI：

  10.1021/jm020471r
• 作为产物：
  描述：

  2-(2-硝基苯基)乙醇 在 nickel(II) triflate 、 氢气 、 1,2-双(二环己基磷基)-乙烷 作用下， 以 甲醇 、 正庚烷 为溶剂， 20.0~120.0 ℃ 、300.01 kPa 条件下， 反应 11.0h， 生成 1-(furan-2-ylmethyl)-1H-indole
  参考文献：
  名称：

  镍催化氨基醇及醇类直接合成N-取代吲哚

  摘要：

  报道了在无添加剂和无碱条件下从氨基醇和醇合成N-取代吲哚的单锅级联方法，释放的水是唯一的化学计量副产物。市售的稳定型 Ni(OTf) 2盐与 1,2-双（二环己基膦基）乙烷 (dcype) 相结合，对于这种前所未有的催化转化非常有效。在反应条件下使用范围广泛的底物，包括芳香族和脂肪族伯醇、环状和非环状仲醇以及各种取代的 2-氨基苯基乙醇，以提供各种N-烷基化吲哚。机理研究表明，反应通过串联N-通过氢自动转移进行烷基化，然后是N-烷基化醇中间体的环化。

  DOI：

  10.1021/acs.orglett.2c03617

文献信息

• Brønsted Acid-Catalyzed Decarboxylative Redox Amination: Formation of <i>N</i>-Alkylindoles from Azomethine Ylides by Isomerization
  作者：Hui Mao、Sichang Wang、Peng Yu、Huiqing Lv、Runsheng Xu、Yuanjiang Pan

  DOI：10.1021/jo102218v

  日期：2011.2.18

  decarboxylative redox amination involving aldehydes with 2-carboxyindoline for the synthesis of N-alkylindoles is described. The decarboxylative condensations of aldehydes with 2-carboxyindoline produce azomethine ylides in situ, which then transform into N-alkylindoles by isomerization.

  描述了涉及醛与2-羧基二氢吲哚的布朗斯台德酸催化的脱羧氧化还原胺化反应，用于合成N-烷基吲哚。醛与2-羧基二氢吲哚的脱羧缩合反应原位产生偶氮甲亚胺，然后通过异构化反应转化为N-烷基吲哚。
• Tunable Hydride Transfer in the Redox Amination of Indoline with Aldehyde: An Attractive Intramolecular Hydrogen-Bond Effect
  作者：Hui Mao、Runsheng Xu、Jieping Wan、Zhengyang Jiang、Cuirong Sun、Yuanjiang Pan

  DOI：10.1002/chem.201001896

  日期：2010.12.3

  Hydride hijacked by “hydrogen”! N‐Alkylindoles and N‐alkylindolines were obtained in the redox amination of indoline with aldehyde, which was tuned by a hydrogen‐bond effect. Salicylaldehyde gave the indoline‐type product via intermolecular hydride transfer, while other aromatic aldehydes gave the indole‐type product via intramolecular hydride transfer.

  氢化物被“氢”劫持！ N-炔基吲哚和N-烷基二氢吲哚是在二氢吲哚与醛的氧化还原胺化反应中获得的，醛可通过氢键效应进行调节。水杨醛通过分子间氢化物转移得到吲哚型产物，而其他芳族醛通过分子内氢化物转移得到吲哚型产物。
• Redox Isomerization via Azomethine Ylide Intermediates: <i>N</i>-Alkyl Indoles from Indolines and Aldehydes
  作者：Indubhusan Deb、Deepankar Das、Daniel Seidel

  DOI：10.1021/ol1031359

  日期：2011.2.18

  Indolines react with aromatic and heteroaromatic aldehydes to yield N-alkyl indoles in a benzoic acid catalyzed redox isomerization reaction. Azomethine ylides are intermediates in this process which was established by intramolecular [3 + 2] trapping experiments.

  二氢吲哚在苯甲酸催化的氧化还原异构化反应中与芳族和杂芳族醛反应生成N-烷基吲哚。甲亚甲胺基化物是该过程的中间体，该过程是通过分子内[3 + 2]捕获实验建立的。
• Montmorillonite K10 catalyzed facile synthesis of <i>N</i>-substituted indoles from primary amines and Morita–Baylis–Hillman acetate of cyclohexenone
  作者：Juqing Han、Luxia Guo、Fuwei Zhang、Minghao Li、Yanlong Gu

  DOI：10.1039/d2gc03997d

  日期：——

  The simultaneous construction of both rings of indole from primary amines and MBH acetate of cyclohexenone is established. This method employed montmorillonite K10 as a cheap catalyst and diethyl carbonate as a green solvent. The scope of the reaction was scouted, in which 37 N-substituted indoles including 1,1′-bisindole were obtained.

  建立了从伯胺和环己烯酮的 MBH 乙酸盐同时构建吲哚的两个环。该方法使用蒙脱石K10作为廉价催化剂和碳酸二乙酯作为绿色溶剂。考察了反应范围，得到了包括1,1'-双吲哚在内的37个N-取代吲哚。
• Novel compounds and methods of use thereof
  申请人：——

  公开号：US20030181482A1

  公开（公告）日：2003-09-25

  This invention relates to novel heteroatom containing compounds and compositions thereof, and their use for the prevention and treatment of disease. The invention also provides for methods of making the compounds. The invention is based on the discovery that certain heteroatom containing compounds, 3-oxoacetamideindolyl compounds, have potent anticancer, cytotoxic, and anti-angiogenic activity.

  本发明涉及含有杂原子的新型化合物及其组合物，以及它们在预防和治疗疾病方面的用途。本发明还提供了制造这些化合物的方法。本发明的基础是发现某些含杂原子的化合物--3-氧代乙酰胺吲哚基化合物具有强效的抗癌、细胞毒性和抗血管生成活性。