2-(3-chlorophenyl)-1H-perimidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(3-chlorophenyl)-1H-perimidine
• 化学式: C₁₇H₁₁ClN₂
• 分子量: 278.741
• InChiKey: IYXXKUGSAHZTRA-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-(3-chlorophenyl)-1H-perimidine 、 碘甲烷 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel perimidine o-quinone derivatives as non-intercalative topoisomerase II catalytic inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bioorg.2019.103131
• 作为产物：
  描述：

  3-氯苯甲醛 、 1,8-二氨基萘 在 sodium metabisulfite 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 2-(3-chlorophenyl)-1H-perimidine
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel perimidine o-quinone derivatives as non-intercalative topoisomerase II catalytic inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bioorg.2019.103131

文献信息

• A Cobalt Catalyst Permits the Direct Hydrogenative Synthesis of 1 <i>H</i> ‐Perimidines from a Dinitroarene and an Aldehyde
  作者：Tobias Schwob、Mirco Ade、Rhett Kempe

  DOI：10.1002/cssc.201900498

  日期：2019.7.5

  A new sustainable catalytic reaction, the synthesis of 1H‐ perimidines from a dinitroarene and an aldehyde in the presence of H2, was achieved. An earth‐abundant metal catalyst was developed to permit the efficient, highly chemoselective, and consecutive hydrogenation of dinitroarenes. The catalyst was reusable and easy to handle. The use of a specific Co complex and its pyrolysis at a certain temperature

  实现了一种新的可持续催化反应，即在H 2存在下由二硝基芳烃和醛合成1 H-亚氨基吡啶。开发了一种富含地球的金属催化剂，可实现对二硝基芳烃的高效，高度化学选择性和连续氢化。该催化剂是可重复使用的并且易于处理。使用特定的Co配合物及其在一定温度下的热解对于实现有机物转化的高活性至关重要。苯甲醛和脂肪醛可能会发生加氢缩合反应，因此可以容忍许多官能团，包括对碘敏感的芳基，腈基，烯烃和炔基等加氢敏感的例子。