3-(3-Hydroxy-4-methoxy-phenyl)-1H-1,3b-diaza-cyclopenta[a]pentalen-7-one | 757189-15-4

• 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-Hydroxy-4-methoxy-phenyl)-1H-1,3b-diaza-cyclopenta[a]pentalen-7-one
• 英文别名: 3-(3-hydroxy-4-methoxyphenyl)pyrrolo[2,3-b]pyrrolizin-8(1H)-one；3-(3-hydroxy-4-methoxyphenyl)-1H-pyrrolo[2,3-b]pyrrolizin-8-one
• CAS: 757189-15-4
• 化学式: C₁₆H₁₂N₂O₃
• 分子量: 280.283
• InChiKey: ZGMPTJKNNNXAHF-UHFFFAOYSA-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：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Acetic acid 2-methoxy-5-(7-oxo-1,7-dihydro-1,3b-diaza-cyclopenta[a]pentalen-3-yl)-phenyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 3-(3-Hydroxy-4-methoxy-phenyl)-1H-1,3b-diaza-cyclopenta[a]pentalen-7-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

• Synthesis of new dipyrrolo- and furopyrrolopyrazinones related to tripentones and their biological evaluation as potential kinases (CDKs1–5, GSK-3) inhibitors
  作者：Christophe Rochais、Nghia Vu Duc、Elodie Lescot、Jana Sopkova-de Oliveira Santos、Ronan Bureau、Laurent Meijer、Patrick Dallemagne、Sylvain Rault

  DOI：10.1016/j.ejmech.2008.05.011

  日期：2009.2

  We herein describe the synthesis of novel dipyrrolo- and furopyrrolopyrazinones related to highly cytotoxic tripentones and to their oximes. The synthetic pathway involved in particular a Curtius rearrangement and a subsequent cyclisation into the title pyrazinones. The biological evaluation towards various cyclin-dependent kinases (CDKs1-5, GSK-3) highlighted a weak inhibitory activity for the oximes whose SAR was studied by a molecular modeling study. (c) 2008 Elsevier Masson SAS. All rights reserved.
• 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.
• 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。