9-[(4-pyrimidin-2-yl)piperazin-1-yl]-1H-phenalen-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 非那烯类
• 英文名称: 9-[(4-pyrimidin-2-yl)piperazin-1-yl]-1H-phenalen-1-one
• 英文别名: 9-(4-Pyrimidin-2-ylpiperazin-1-yl)phenalen-1-one；9-(4-pyrimidin-2-ylpiperazin-1-yl)phenalen-1-one
• 化学式: C₂₁H₁₈N₄O
• 分子量: 342.4
• InChiKey: LARMBPKMMZMREB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  9-羟基-萘嵌苯-1-酮 在 potassium phosphate 作用下， 以 水 、 甲苯 为溶剂， 反应 5.5h， 生成 9-[(4-pyrimidin-2-yl)piperazin-1-yl]-1H-phenalen-1-one
  参考文献：
  名称：

  Design, synthesis and evaluation of amino-substituted 1H-phenalen-1-ones as anti-leishmanial agents

  摘要：

  Screening of a designed collection of mono-substituted amino-IH-phenalen-1-ones against promastigote forms of L. donovani and L. amazonensis, identified seven compounds with anti-leishmanial activities comparable or better than the commonly prescribed anti-leishmanial drug, miltefosine. Structure activity analysis revealed that appendages containing a basic tertiary nitrogen were favored, and that the position of the appendage also affected their potency. Like miltefosine, several of these active compounds significantly reduced the mitochondrial membrane potential in promastigotes. Further studies in amastigotes of L. amazonensis revealed that compounds 14, 15 and 33 were more active and more selective than miltefosine, with sub-micromolar potencies and selectivity indices > 100. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.10.032

文献信息

• Design, synthesis and evaluation of amino-substituted 1H-phenalen-1-ones as anti-leishmanial agents
  作者：Mónica Blanco Freijo、Atteneri López-Arencibia、José E. Piñero、Grant McNaughton-Smith、Teresa Abad-Grillo

  DOI：10.1016/j.ejmech.2017.10.032

  日期：2018.1

  Screening of a designed collection of mono-substituted amino-IH-phenalen-1-ones against promastigote forms of L. donovani and L. amazonensis, identified seven compounds with anti-leishmanial activities comparable or better than the commonly prescribed anti-leishmanial drug, miltefosine. Structure activity analysis revealed that appendages containing a basic tertiary nitrogen were favored, and that the position of the appendage also affected their potency. Like miltefosine, several of these active compounds significantly reduced the mitochondrial membrane potential in promastigotes. Further studies in amastigotes of L. amazonensis revealed that compounds 14, 15 and 33 were more active and more selective than miltefosine, with sub-micromolar potencies and selectivity indices > 100. (C) 2017 Elsevier Masson SAS. All rights reserved.