N-benzyl-1-phenanthren-9-ylmethanimine oxide | 875119-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N-benzyl-1-phenanthren-9-ylmethanimine oxide
• CAS: 875119-98-5
• 化学式: C₂₂H₁₇NO
• 分子量: 311.383
• InChiKey: QGGWZXNSIGIZRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-benzyl-1-phenanthren-9-ylmethanimine oxide 、 异氰酸对硝基苯 反应 24.0h， 以81%的产率得到2-benzyl-4-(4-nitrophenyl)-3-(phenanthren-9-yl)-1,2,4-oxadiazolidin-5-one
  参考文献：
  名称：

  1,2,4-氧杂二唑-5-酮类药物他莫昔芬的类似物：合成和生物学评估。

  摘要：

  已经制备了一系列2,3,4-三芳基取代的1,2,4-恶二唑-5-酮作为他莫昔芬（TAM）的固定环类似物，他莫昔芬是用于乳腺癌的雌二醇受体（ER）的药物抑制剂通过基于硝酮与异氰酸酯的1,3-偶极环加成反应的高效合成方案进行治疗。一些新合成的化合物（14d-f，14h和14k）在具有50.63至31.82μM的IC50值的人乳腺癌细胞系（MCF-7）中显示出明显的细胞毒性作用。另外，化合物14d-f，14h和14k能够增加p53表达水平，也激活细胞凋亡途径。在ER的晶体结构上进行的新型化合物的分子建模研究表明，与TAM相似，与配体的芳环之间存在强烈的疏水相互作用。这些数据表明1,2，

  DOI：

  10.1039/c9ob00651f

文献信息

• Isoxazolidinyl polycyclic aromatic hydrocarbons as DNA-intercalating antitumor agents
  作者：Antonio Rescifina、Ugo Chiacchio、Antonino Corsaro、Anna Piperno、Roberto Romeo

  DOI：10.1016/j.ejmech.2010.10.023

  日期：2011.1

  The second generation and an isosteric series of isoxazolidinyl polycyclic aromatic hydrocarbons, as DNA-intercalator agents designed to act on remotely implanted tumors, have been synthesized in good yields according to the 1,3-dipolar cycloaddition methodology. The structure of the obtained cyclo-adducts has been determined by NOE experiments and supported by computational studies at PM3 level. The utility of this new template in the synthesis of structures designed to capitalize on its intercalative properties has been examined. All the obtained compounds have been tested for their in vitro cytotoxic activity and the most potent of them showed an IC50 of 9 mu M upon the human lung cancer (A-549) cell and a binding constant, for the intercalation with calf thymus DNA, of 9.6 x 10(4) M-1. Biological and docking studies showed that these compounds complex exclusively by intercalation between base pairs, approaching the DNA from its minor groove, with a neat selectivity for the AT or GC nucleobases. (C) 2010 Elsevier Masson SAS. All rights reserved.