1-(pyren-1-yl)-1H-pyrrole | 1222830-16-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1-(pyren-1-yl)-1H-pyrrole
• 英文别名: 1-Pyren-1-ylpyrrole；1-pyren-1-ylpyrrole
• CAS: 1222830-16-1
• 化学式: C₂₀H₁₃N
• 分子量: 267.33
• InChiKey: LSWIIQXVZAHUGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2,5-二甲氧基四氢呋喃 、 4-氨基芘 在 bismuth (III) nitrate pentahydrate 作用下， 反应 0.25h， 以87%的产率得到1-(pyren-1-yl)-1H-pyrrole
  参考文献：
  名称：

  Ultrasound-assisted bismuth nitrate-induced green synthesis of novel pyrrole derivatives and their biological evaluation as anticancer agents

  摘要：

  A series of novel N-substituted pyrrole derivatives have been designed and synthesized following ultrasound-assisted and bismuth nitrate-catalyzed eco-friendly route. This reaction has also provided a general method to prepare diverse varieties of N-substituted pyrroles with less nucleophilic polyaromatic amines. Based on H-1 NMR spectroscopy, a plausible mechanistic pathway has been advanced. Cytotoxicity of some selected N-substituted pyrrole derivatives has been evaluated in vitro in a panel of mammalian cancer cell lines which includes liver cancer cell lines (HepG2 and Hepa1-6), colon cancer cell lines (HT-29 and Caco-2), a cervical cancer cell line (HeLa) and NIH3T3 cells. Two compounds, 5-(1H-pyrrol-1-yl)-1,10-phenanthroline (9) and 1-(phenanthren-2-yl)-1H-pyrrole (10) have shown good cytotoxicity against some cancer cell lines. Furthermore, these compounds have exhibited cytotoxic specificity against liver cancer cell lines in vitro when compared with normal cultured primary hepatocytes. (C) 2012 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2012.01.055

文献信息

• 硝基芳烃脱硝偶联合成N-芳基吡咯和N-芳基吲哚的方法
  申请人：广西大学

  公开号：CN114380730A

  公开（公告）日：2022-04-22

  本发明公开了一种硝基芳烃脱硝偶联合成N‑芳基吡咯和N‑芳基吲哚的方法，以吡咯、吲哚类含氮芳香杂环化合物与硝基芳烃为原料，在过渡金属催化下，通过硝基芳烃与吡咯、吲哚类含氮芳杂环的碳‑氮键脱硝偶联的方式直接生成N‑芳基化吡咯、N‑芳基化吲哚类化合物。与传统方法相比，本发明在合成条件和实用性方面有明显的优势，它具有合成步骤简单、操作简便、原料价廉易得、对官能团兼容性好、化学选择性以及原子经济性高等优点，也更加符合绿色和可持续化学的理念，为此类具有广泛应用价值的化合物的高效合成提供了参考和可靠的技术支持。
• COPOLYMER OF PYRENE AND PYRROLE AND METHOD OF PRODUCING THE COPOLYMER
  申请人：Tongji University

  公开号：EP2576645A1

  公开（公告）日：2013-04-10
• Ultrasound-assisted bismuth nitrate-induced green synthesis of novel pyrrole derivatives and their biological evaluation as anticancer agents
  作者：Debasish Bandyopadhyay、Sanghamitra Mukherjee、Jose C. Granados、John D. Short、Bimal K. Banik

  DOI：10.1016/j.ejmech.2012.01.055

  日期：2012.4

  A series of novel N-substituted pyrrole derivatives have been designed and synthesized following ultrasound-assisted and bismuth nitrate-catalyzed eco-friendly route. This reaction has also provided a general method to prepare diverse varieties of N-substituted pyrroles with less nucleophilic polyaromatic amines. Based on H-1 NMR spectroscopy, a plausible mechanistic pathway has been advanced. Cytotoxicity of some selected N-substituted pyrrole derivatives has been evaluated in vitro in a panel of mammalian cancer cell lines which includes liver cancer cell lines (HepG2 and Hepa1-6), colon cancer cell lines (HT-29 and Caco-2), a cervical cancer cell line (HeLa) and NIH3T3 cells. Two compounds, 5-(1H-pyrrol-1-yl)-1,10-phenanthroline (9) and 1-(phenanthren-2-yl)-1H-pyrrole (10) have shown good cytotoxicity against some cancer cell lines. Furthermore, these compounds have exhibited cytotoxic specificity against liver cancer cell lines in vitro when compared with normal cultured primary hepatocytes. (C) 2012 Published by Elsevier Masson SAS.