C-(1-pyrenyl)-N-(2-hydroxybenzyl)nitrone | 1394382-15-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: C-(1-pyrenyl)-N-(2-hydroxybenzyl)nitrone
• CAS: 1394382-15-0；1394382-16-1
• 化学式: C₂₄H₁₇NO₂
• 分子量: 351.404
• InChiKey: COFDQHZEHOIXAY-QFEZKATASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  46.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  C-(1-pyrenyl)-N-(2-hydroxybenzyl)nitrone 、 烯丙醇 以 甲苯 为溶剂， 反应 12.0h， 以50%的产率得到2-{[(3RS,5SR)-5-(hydroxymethyl)-3-pyren-1-ylisoxazolidin-2-yl]methyl}phenol
  参考文献：
  名称：

  Synthesis and biological activity of novel bifunctional isoxazolidinyl polycyclic aromatic hydrocarbons

  摘要：

  This paper reports the synthesis and the biological properties of two novel pyrene-bearing isoxazolidinyl derivatives able to exhibit antitumor activity by DNA intercalation. The synthetic approach exploits a consolidated protocol based on 1,3-dipolar cycloaddition reaction. The intercalating properties have been determined by combining electrophoresis studies with molecular docking, while the antitumor activity has been evaluated over five carcinoma cell lines. The obtained compounds show also a good affinity towards silver cations; the presence of a 2-hydroxybenzyl appendage on the isoxazolidine ring ensures a good affinity and selectivity in the binding. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.035
• 作为产物：
  描述：

  水杨醛肟 、 1-芘甲醛 在 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到C-(1-pyrenyl)-N-(2-hydroxybenzyl)nitrone
  参考文献：
  名称：

  Synthesis and biological activity of novel bifunctional isoxazolidinyl polycyclic aromatic hydrocarbons

  摘要：

  This paper reports the synthesis and the biological properties of two novel pyrene-bearing isoxazolidinyl derivatives able to exhibit antitumor activity by DNA intercalation. The synthetic approach exploits a consolidated protocol based on 1,3-dipolar cycloaddition reaction. The intercalating properties have been determined by combining electrophoresis studies with molecular docking, while the antitumor activity has been evaluated over five carcinoma cell lines. The obtained compounds show also a good affinity towards silver cations; the presence of a 2-hydroxybenzyl appendage on the isoxazolidine ring ensures a good affinity and selectivity in the binding. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.035