3-(3-benzyloxy-4-methoxyphenyl)-1-benzylpyrrolo[2,3-b]pyrrolizin-8(1H)-one | 757188-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(3-benzyloxy-4-methoxyphenyl)-1-benzylpyrrolo[2,3-b]pyrrolizin-8(1H)-one
• 英文别名: 1-Benzyl-3-(4-methoxy-3-phenylmethoxyphenyl)pyrrolo[2,3-b]pyrrolizin-8-one；1-benzyl-3-(4-methoxy-3-phenylmethoxyphenyl)pyrrolo[2,3-b]pyrrolizin-8-one
• CAS: 757188-78-6
• 化学式: C₃₀H₂₄N₂O₃
• 分子量: 460.532
• InChiKey: DAYQUMNAEMVQKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  45.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-benzyloxy-4-methoxyphenyl)-1-benzylpyrrolo[2,3-b]pyrrolizin-8(1H)-one 在 palladium on activated charcoal 氢溴酸 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 1-benzyl-3-(3-hydroxy-4-methoxyphenyl)-5,6,7,7a-tetrahydropyrrolo[2,3-b]pyrrolizin-8(1H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel pyrrolopyrrolizinones as anticancer agents

  摘要：

  We herein describe the synthesis of novel 3-(het)aryl-pyrrolo[2,3-b]pyrrolizin-8(1H)-ones starting from commercial (het)aryl-acetonitriles. A more convergent route was also described through the first synthesis of ethyl 3-amino-4-bromo-1H-pyrrole-2-carboxylate 17. The antiproliferative activities of these compounds were tested toward various cell lines and one of them 10k shows interesting cytotoxic properties, although it was less potent than our lead compound in thiophene series 1k. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.022
• 作为产物：
  描述：

  methyl 4'-(3-benzyloxy-4-methoxyphenyl)-1'H-1,3'-bipyrrole-2'-carboxylate 在 sodium hydride 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 3-(3-benzyloxy-4-methoxyphenyl)-1-benzylpyrrolo[2,3-b]pyrrolizin-8(1H)-one
  参考文献：
  名称：

  首次合成芳基吡咯并吡咯并吡咯并酮作为有用的物质，具有潜在的生物学意义

  摘要：

  新型芳基吡咯并吡咯并吡咯并吡嗪酮是通过三步或四步制备的，从氨基芳基吡咯和吡唑羧酸酯开始，通过Vilsmeier-Haack中间体的环化反应。通过氮杂杂环的各种N-保护增强了该合成，并提供了具有潜在生物学意义的新系列。

  DOI：

  10.1016/j.tetlet.2004.06.047

文献信息

• First synthesis of arylpyrrolo- and pyrazolopyrrolizinones as useful agents with potential biological interest
  作者：Christophe Rochais、Vincent Lisowski、Patrick Dallemagne、Sylvain Rault

  DOI：10.1016/j.tetlet.2004.06.047

  日期：2004.8

  three or four steps starting from aminoarylpyrrole and pyrazole carboxylates through the cyclisation of a Vilsmeier–Haack intermediate. This synthesis was enhanced by diverse N-protections of the aza-heterocycle and furnish new series with potential biological interest.

  新型芳基吡咯并吡咯并吡咯并吡嗪酮是通过三步或四步制备的，从氨基芳基吡咯和吡唑羧酸酯开始，通过Vilsmeier-Haack中间体的环化反应。通过氮杂杂环的各种N-保护增强了该合成，并提供了具有潜在生物学意义的新系列。
• Hydrogenative desulphurization of thienopyrrolizinones: An easy and selective access to (Z)-phenethylidenepyrrolizinones with in vitro cytotoxic activity
  作者：Vittoria Perri、Christophe Rochais、Jana Sopkova-de Oliveira Santos、Rémi Legay、Thierry Cresteil、Patrick Dallemagne、Sylvain Rault

  DOI：10.1016/j.ejmech.2009.12.021

  日期：2010.3

  Attempts in view to dearomatize some previously reported tripentones with potent antineoplastic activities led in thiophene series to an unexpected hydrogenative desulphurization reaction. The resulting (Z)-phenethylidenepyrrolizinones were tested in vitro over human epidermoid carcinoma KB cell line. The results of this biological evaluation indicated that the tricyclic core of our model can be cleaved with a partial respect of the activity. (C) 2009 Published by Elsevier Masson SAS.
• Synthesis and biological evaluation of novel pyrrolopyrrolizinones as anticancer agents
  作者：C. Rochais、V. Lisowski、P. Dallemagne、S. Rault

  DOI：10.1016/j.bmc.2006.09.022

  日期：2006.12

  We herein describe the synthesis of novel 3-(het)aryl-pyrrolo[2,3-b]pyrrolizin-8(1H)-ones starting from commercial (het)aryl-acetonitriles. A more convergent route was also described through the first synthesis of ethyl 3-amino-4-bromo-1H-pyrrole-2-carboxylate 17. The antiproliferative activities of these compounds were tested toward various cell lines and one of them 10k shows interesting cytotoxic properties, although it was less potent than our lead compound in thiophene series 1k. (c) 2006 Elsevier Ltd. All rights reserved.