2-(2-chlorophenyl)-1H-perimidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类 - 二氮杂萘
• 英文名称: 2-(2-chlorophenyl)-1H-perimidine
• 化学式: C₁₇H₁₁ClN₂
• 分子量: 278.741
• InChiKey: NRDIHDDECFVHQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2-chlorophenyl)-1H-perimidine 在 甲烷磺酸 作用下， 以 neat (no solvent) 为溶剂， 反应 0.08h， 生成 7-bromo-2-(2-chlorophenyl)benzo[gh]perimidine
  参考文献：
  名称：

  7-溴-1,3-二氮杂戊烯的合成

  摘要：

  以前无法获得的7-溴-1,3-二氮杂戊烯类可以通过容易获得的7-（5-溴-3,4-二氢嘧啶-4-基）-1H-嘧啶的熔体周环合成来合成。

  DOI：

  10.1002/ejoc.201800703
• 作为产物：
  描述：

  5-(2-氯苄亚基)-2,2-二甲基-1,3-二恶烷-4,6-二酮 、 1,8-二氨基萘 以 乙醇 为溶剂， 反应 4.5h， 以84%的产率得到2-(2-chlorophenyl)-1H-perimidine
  参考文献：
  名称：

  使用亚芳基 Meldrum 酸作为芳基和氧化剂的来源合成 2-芳基-1H-苯并咪唑和 2-芳基-1H-perimidines

  摘要：

  亚芳基 Meldrum 酸被用作芳基的来源和氧化剂，用于通过与 1,2-苯二胺在回流乙醇中的缩合反应合成 2-芳基-1H-苯并咪唑，收率良好至高。亚芳基 Meldrum 的酸也被用作芳基的来源和氧化剂，用于通过与 1,8-二氨基萘在回流乙醇中的缩合反应以高产率合成 2-芳基-1H-脒。

  DOI：

  10.3184/174751918x15199196317528

文献信息

• Pyrimidines as Surrogates for 1,3-Dicarbonyl Compounds in<i>peri</i>Annulation of Perimidines en Route to 1,3-Diazapyrenes
  作者：Alexander V. Aksenov、Stanisvlav V. Shcherbakov、Irina V. Lobach、Inna V. Aksenova、Michael Rubin

  DOI：10.1002/ejoc.201601589

  日期：2017.3.27

  A highly efficient protocol for acid-mediated peri-annulation of perimidines with pyrimidines was developed. Pyrimidines, used as surrogates for 1,3-dicarbonyl compounds allow for furnishing benzo[gh]perimidines, including hardly available analogs, non-substituted, or mono-substituted at C-6, C-8. Limitations of reactions employing 5-bromopyrimidines are investigated.

  开发了一种用于酸介导的嘧啶环化环化的高效方案。用作 1,3-二羰基化合物替代物的嘧啶允许提供苯并[gh] 嘧啶，包括几乎无法获得的类似物、未取代的或在 C-6、C-8 处单取代的类似物。研究了使用 5-溴嘧啶的反应的局限性。
• Magnetic Graphene Oxide Bearing ZrO₂ as a New Composite Catalyst for the Synthesis of 1<i>H</i>-Perimidines
  作者：M. A. Amrollahi、F. Ashayeri-Harati

  DOI：10.1080/00304948.2020.1761227

  日期：2020.7.3
• Design, synthesis and biological evaluation of novel perimidine o-quinone derivatives as non-intercalative topoisomerase II catalytic inhibitors
  作者：Du-Chao Zhou、Yu-Ting Lu、Yan-Wen Mai、Chen Zhang、Jie Xia、Pei-Fen Yao、Hong-Gen Wang、Shi-Liang Huang、Zhi-Shu Huang

  DOI：10.1016/j.bioorg.2019.103131

  日期：2019.10

  For the development of novel anticancer agents, we designed and synthesized a total of 37 perimidine o-quinone derivatives containing the o-quinone group at the A or B ring and different substituents (alkyl groups, aryl groups or heterocycles) at the C ring of the compounds. The structure-activity relationships (SARs) were established based on the cytotoxicity data of compounds from the HL-60, Huh7, Hct116, and Hela cell lines. The cytotoxicity results showed that most compounds exhibited potent cytotoxicity. In particular, compound b-12 showed the best anti-proliferative activity (IC50 <= 1 mu M) against four cancer cell lines and strong potency against the HL-60/MX2 (0.47 mu M) cell line, which is resistant to Topo II poisons. Further studies showed that b-12 exhibited potent Topo II alpha inhibitory activity (IC50 = 7.54 mu M) compared with Topo I, which acted as a class of non-intercalative Topo IIa catalytic inhibitor by inhibiting the ATP binding site of Topo II. Cell apoptosis and cell cycle assays confirmed that b-12 could induce the apoptosis of Huh7 cells in a dose-dependent manner.
• Synthesis of 2-aryl-1<i>H</i>-Benzimidazoles and 2-aryl-1<i>H</i>-perimidines Using Arylidene Meldrum's Acid as a Source of the Aryl Group and Oxidant
  作者：Hossein Mehrabi、Faezeh Najafian-Ashrafi、Zeinab Esfandiarpour、Reza Ranjbar-Karimi

  DOI：10.3184/174751918x15199196317528

  日期：2018.3

  Arylidene Meldrum's acid is employed as a source of the aryl group and oxidant for the synthesis of 2-aryl-1H–benzimidazoles by a condensation reaction with 1,2-phenylenediamine in refluxing ethanol with good to high yields. Arylidene Meldrum's acids were also used as a source of the aryl group and oxidant for the synthesis of 2-aryl-1H-perimidines by a condensation reaction with 1,8-diaminonaphthalene

  亚芳基 Meldrum 酸被用作芳基的来源和氧化剂，用于通过与 1,2-苯二胺在回流乙醇中的缩合反应合成 2-芳基-1H-苯并咪唑，收率良好至高。亚芳基 Meldrum 的酸也被用作芳基的来源和氧化剂，用于通过与 1,8-二氨基萘在回流乙醇中的缩合反应以高产率合成 2-芳基-1H-脒。
• Synthesis of 7-Bromo-1,3-diazapyrenes
  作者：Alexander V. Aksenov、Stanisvlav V. Shcherbakov、Irina V. Lobach、Leonid G. Voskressensky、Michael Rubin

  DOI：10.1002/ejoc.201800703

  日期：2018.8.15

  Previously inaccessible 7‐bromo‐1,3‐diazapyrenes can be synthesized by an in‐melt peri‐cyclization of readily available 7‐(5‐bromo‐3,4‐dihydropyrimidin‐4‐yl)‐1H‐perimidines.

  以前无法获得的7-溴-1,3-二氮杂戊烯类可以通过容易获得的7-（5-溴-3,4-二氢嘧啶-4-基）-1H-嘧啶的熔体周环合成来合成。