(5-{[(4-chlorobenzoyl)oxy]methyl}-4-acridinyl)methyl-4-chlorobenzoate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (5-{[(4-chlorobenzoyl)oxy]methyl}-4-acridinyl)methyl-4-chlorobenzoate
• 英文别名: acridin-4,5-yl-dimethyl-bis-4-chlorobenzoate；[5-[(4-Chlorobenzoyl)oxymethyl]acridin-4-yl]methyl 4-chlorobenzoate
• 化学式: C₂₉H₁₉Cl₂NO₄
• 分子量: 516.38
• InChiKey: ZDECFOLPJZLLPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吖啶 在 4-二甲氨基吡啶 、 硫酸 、 三乙胺 、 calcium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (5-{[(4-chlorobenzoyl)oxy]methyl}-4-acridinyl)methyl-4-chlorobenzoate
  参考文献：
  名称：

  吖啶环的反应性：吖啶和一些衍生物的一锅区域选择性单溴甲基化和双溴甲基化

  摘要：

  我们在此报告了 4-溴甲基吖啶和 4,5-双-（溴甲基）吖啶的新的有效区域选择性合成路线，这是用于各种 4-亚甲基吖啶和 4,5-双-（亚甲基）吖啶衍生物的两种有趣的起始材料，在一个用溴甲基甲基醚 (BMME) 直接对吖啶进行溴甲基化。我们还描述了来自相应的 4,5-双（羟甲基）吖啶前体的一些生物学上有趣的二酯衍生物。

  DOI：

  10.1055/s-2003-42104

文献信息

• Reactivity of the Acridine Ring: One-Pot Regioselective Single and Double Bromomethylation of Acridine and Some Derivatives
  作者：Julien Chiron、Jean-Pierre Galy

  DOI：10.1055/s-2003-42104

  日期：——

  here a new efficient regioselective synthetic route to 4-bromomethylacridine and to 4,5-bis-(bromomethyl)acridine, two interesting starting materials for various 4-methyleneacridine and 4,5-bis-(methylene)acridine derivatives, in one step by direct bromomethylation of acridine with bromomethylmethylether (BMME). We also describe some biologically interesting diesters derivatives from the corresponding

  我们在此报告了 4-溴甲基吖啶和 4,5-双-（溴甲基）吖啶的新的有效区域选择性合成路线，这是用于各种 4-亚甲基吖啶和 4,5-双-（亚甲基）吖啶衍生物的两种有趣的起始材料，在一个用溴甲基甲基醚 (BMME) 直接对吖啶进行溴甲基化。我们还描述了来自相应的 4,5-双（羟甲基）吖啶前体的一些生物学上有趣的二酯衍生物。
• Synthesis and antileishmanial activities of 4,5-di-substituted acridines as compared to their 4-mono-substituted homologues
  作者：Di Giorgio Carole、De Méo Michel、Chiron Julien、Delmas Florence、Nikoyan Anna、Jean Séverine、Dumenil Gérard、Timon-David Pierre、Galy Jean-Pierre

  DOI：10.1016/j.bmc.2005.06.045

  日期：2005.10

  Newly synthesized 4,5-di-substituted acridines were assessed for in vitro antileishmanial activities as compared to those of their 4-mono-substituted homologues. Mono-substituted acridines exhibited a weak specificity for Leishmania parasites. Di-substituted acridines, on the contrary, displayed interesting amastigote-specific activities through a mechanism of action that might not involve intercalation to DNA. This antileishmanial property, associated with a low antiproliferative activity towards human cells, led to the identification of a new class of promising acridine derivatives such as 4,5-bis(hydroxymethyl)acridine with a nonclassical mechanism of action based on the inhibition of Leishmania internalization within macrophages. In the meantime, the effects of experimental lighting on the biological properties of acridines were assessed: experimental lighting did not significantly improve the antileishmanial activity of the compounds since it produced a greater toxicity against human cells. (c) 2005 Elsevier Ltd. All rights reserved.