2-benzyl-1H-perimidine | 28537-43-1

• 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-benzyl-1H-perimidine
• CAS: 28537-43-1
• 化学式: C₁₈H₁₄N₂
• 分子量: 258.323
• InChiKey: RBWVGGRLNPNWTC-UHFFFAOYSA-N

物化性质

• 熔点：
  194 °C
• 沸点：
  499.2±28.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 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：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-benzyl-1H-perimidine 在 甲烷磺酸 作用下， 以 neat (no solvent) 为溶剂， 反应 0.08h， 生成 2-benzyl-7-bromobenzo[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：

  苯乙醛 、 1,8-二氨基萘 在 sodium metabisulfite 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以95%的产率得到2-benzyl-1H-perimidine
  参考文献：
  名称：

  An Improved One-Pot Method for the Preparation of 2-Substituted 1H-Perimidines

  摘要：

  2-substituted H-1-perimidines are readily prepared, in high yields, by refluxing a mixture of sodium pyrosulfite, an aldehyde, and 1,8-diaminonaphthalene in aqueous ethanol or N,N-dimethylformamide. The method is of wide applicability except from araldehydes bearing a strong electron-withdrawing group (-CN, -NO2).

  DOI：

  10.1080/00397919108055450

文献信息

• Synthesis of New Perimidine Derivatives from the Reaction of 1,8-Diaminonapthalene with Iminoester Hydrochlorides
  作者：Bahittin Kahveci、Nesrin Karaali、Emre Menteşe、Fatih Yilmaz

  DOI：10.3184/174751913x13691578103477

  日期：2013.6

  procedure is described for the synthesis of 2-substituted perimidines involving the reaction of 1,8-diaminonapthalene with iminoester hydrochlorides of substituted phenylacetic acids under microwave irradiation. This leads to good yields in short reaction times. The results were compared with those that used conventional heating. This new method may be preferable for the synthesis of perimidines.

  描述了一种用于合成 2-取代的 perimidines 的替代程序, 包括 1,8-二氨基萘与取代苯乙酸的亚氨基酯盐酸盐在微波辐射下的反应。这导致在较短的反应时间内获得良好的产率。将结果与使用传统加热的结果进行比较。这种新方法可能更适用于合成嘧啶。
• Sachs, Justus Liebigs Annalen der Chemie, 1909, vol. 365, p. 162
  作者：Sachs

  DOI：——

  日期：——
• Reddy, R. Rambhupal; Rao, C. V. Chalapathi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 3, p. 367 - 369
  作者：Reddy, R. Rambhupal、Rao, C. V. Chalapathi

  DOI：——

  日期：——
• An Improved One-Pot Method for the Preparation of 2-Substituted 1H-Perimidines
  作者：André Maquestiau、Laurence Berte、Annie Mayence、Jean-Jacques Vanden Eynde

  DOI：10.1080/00397919108055450

  日期：1991.11

  2-substituted H-1-perimidines are readily prepared, in high yields, by refluxing a mixture of sodium pyrosulfite, an aldehyde, and 1,8-diaminonaphthalene in aqueous ethanol or N,N-dimethylformamide. The method is of wide applicability except from araldehydes bearing a strong electron-withdrawing group (-CN, -NO2).
• 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.