5-iodo-2-(1H-pyrrol-1-yl)aniline | 1620494-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-iodo-2-(1H-pyrrol-1-yl)aniline
• CAS: 1620494-95-2
• 化学式: C₁₀H₉IN₂
• 分子量: 284.099
• InChiKey: RAEZFHSXFZKESA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.95
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-iodo-2-(1H-pyrrol-1-yl)aniline 在 三乙胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 吡啶 为溶剂， 反应 8.0h， 生成 3-iodo-6-(trichloromethyl)pyrrolo[1,2-a]quinoxaline
  参考文献：
  名称：

  Synthesis and in vitro evaluation of 4-trichloromethylpyrrolo[1,2-a]quinoxalines as new antiplasmodial agents

  摘要：

  Thanks to a preliminary in vitro screening of several CCl3-substituted-nitrogen containing heterocycles belonging to our chemical library, the 2-trichloromethylquinoxaline scaffold appeared to be of potential interest for developing new antiplasmodial agents. Then, combining these experimental results to the antimalarial properties reported for various pyrrolo[1,2-a]quinoxaline derivatives, an original series of fifteen 7-substituted-4-trichoromethylpyrrolo[1,2-a]quinoxalines was synthesized in a 4 to 5 reaction steps pathway. All molecules were evaluated in vitro toward both their antiplasmodial activity on the K1 multi-resistant Plasmodium falciparum strain and their cytotoxicity on the HepG2 human cell line. Thus, 3 hit molecules were identified, displaying IC50 values in the micromolar range and low cytotoxicity values, reaching good selectivity indexes, in comparison with the reference drugs chloroquine and doxycycline. Structure-activity relationship studies showed that the pyrrolo[1,2-a]quinoxaline scaffold can support selective antiplasmodial activity when substituted at position 4 by a CCl3 group. However, substitution at position 7 of the same scaffold is neither beneficial for cytotoxicity nor favourable for the solubility in the biological media.

  DOI：

  10.1016/j.ejmech.2014.06.014
• 作为产物：
  描述：

  1-(4-iodo-2-nitrophenyl)-1H-pyrrole 在 铁粉 、 氯化铵 作用下， 以 水 为溶剂， 生成 5-iodo-2-(1H-pyrrol-1-yl)aniline
  参考文献：
  名称：

  通过Mamedov杂环重排简单而绿色地合成苯并咪唑和吡咯并[1,2-a]喹喔啉

  摘要：

  本文报道了通过Mamedov杂环重排合成苯并咪唑与吡咯并[1,2- a ]喹喔啉的偶联化合物的方法。该方法在室温下进行，仅需要溶剂（HOAc）。以中等至良好的产率获得了一系列4-（1 H-苯并[ d ]咪唑-2-基）吡咯并[1,2- a ]喹喔啉衍生物。

  DOI：

  10.1039/d1nj01251g

文献信息

• Application of <i>N</i>,<i>N</i>-Dimethylethanolamine as a One-Carbon Synthon for the Synthesis of Pyrrolo[1,2-<i>a</i>]quinoxalines, Quinazolin-4-ones, and Benzo[4,5]imidazoquinazolines <i>via</i> [5 + 1] Annulation
  作者：Meiqi Geng、Minzhao Huang、Jinqiang Kuang、Weiwei Fang、MaoZhong Miao、Yongmin Ma

  DOI：10.1021/acs.joc.2c02079

  日期：2022.11.4

  synthetic chemistry. In this report, a Cu(II)-catalyzed green and efficient synthesis of pyrrolo[1,2-a]quinoxaline, quinazolin-4-one, and benzo[4,5]imidazoquinazoline derivatives was developed, employing N,N-dimethylethanolamine (DMEA) as a C1 synthon. Green oxidant O2 is critical in these transformations, facilitating the formation of a key intermediate─a reactive iminium ion. The method conducted

  N-杂环的合成是合成化学的重要组成部分。在本报告中，采用N,N-二甲基乙醇胺开发了 Cu(II) 催化绿色高效合成吡咯并[1,2 - a ]喹喔啉、喹唑啉-4-酮和苯并[4,5]咪唑并喹唑啉衍生物(DMEA) 作为 C1 合成子。绿色氧化剂 O 2在这些转化过程中至关重要，它促进了关键中间体的形成——活性亚胺离子。在温和条件下进行的方法与多种功能组兼容，为以前开发的协议提供了一个有吸引力的替代方案。
• A Direct Method for Synthesis of Quinoxalines and Quinazolinones Using Epoxides as Alkyl Precursor
  作者：Xueyan Lv、Lili Lv、Shichen Li、Chengcheng Ding、Bingchuan Yang、Chen Ma

  DOI：10.3390/molecules28217391

  日期：——

  An iodine-mediated one-pot synthesis of pyrrolo/indolo [1,2-a]quinoxalines and quinazolin-4-one via utilizing epoxides as alkyl precursors under metal-free conditions has been described. Both 1-(2-aminophenyl)-pyrrole and 2-aminobenzamide could be applied to this protocol. A total of 33 desired products were obtained with moderate to good yields. This methodology was suitable for wide-scale preparation

  描述了在无金属条件下利用环氧化物作为烷基前体，碘介导的吡咯并/吲哚[1,2-a]喹喔啉和喹唑啉-4-酮的一锅法合成。1-(2-氨基苯基)-吡咯和2-氨基苯甲酰胺都可以应用于该方案。总共获得了 33 种所需产物，收率中等至良好。该方法适合大规模制备，所得产品可以进一步修饰为有前景的药物活性试剂。