N-(pyrimidin-4′-ylmethyl)-3,9-dioxa-6-azaundecane-1,11-diol | 1346227-63-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(pyrimidin-4′-ylmethyl)-3,9-dioxa-6-azaundecane-1,11-diol
• 英文别名: N-(pyrimidin-4'-ylmethyl)-3,9-dioxa-6-azaunedecane-1,11-diol；2-[2-[2-(2-Hydroxyethoxy)ethyl-(pyrimidin-4-ylmethyl)amino]ethoxy]ethanol；2-[2-[2-(2-hydroxyethoxy)ethyl-(pyrimidin-4-ylmethyl)amino]ethoxy]ethanol
• CAS: 1346227-63-1
• 化学式: C₁₃H₂₃N₃O₄
• 分子量: 285.343
• InChiKey: ZAGSZTPSPDCHBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  87.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(pyrimidin-4′-ylmethyl)-3,9-dioxa-6-azaundecane-1,11-diol 、 4-羟基黄烷酮 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以29%的产率得到1,13-bis[4'-(4H-chromen-4-on-2-yl)phenyl]-7-(4-pyrimidinylmethyl)-1,4,10,13-tetraoxa-7-azatridecane
  参考文献：
  名称：

  Flavonoid Dimers as Novel, Potent Antileishmanial Agents

  摘要：

  The present study found that synthetic flavonoid dimers with either polyethylene glycol linker or amino ethyleneglycol linker have marked leishmanicidal activity. Compound 39 showed very consistent and promising leishmanicidal activity for both extracellular promastigotes (IC50 ranging from 0.13 to 0.21 mu M) and intracellular amastigotes (IC50 = 0.63 mu M) irrespective of the drug-sensitivity of parasites. Moreover, compound 39 displayed no toxicity toward macrophage RAW 264.7 cells (IC50 > 100 mu M) and primary mouse peritoneal elicited macrophages (IC50 > 88 mu M). Its high value of therapeutic index (> 140) was better than other highly potent antileishmanials such as amphotericin B (therapeutic index = 119). Compound 39 is therefore a new, safe, and effective antileishmanial candidate compound which is even effective against drug-refractory parasites.

  DOI：

  10.1021/jm301172v
• 作为产物：
  描述：

  NH-BIS(一聚乙二醇-羟基) 、 4-(溴甲基)嘧啶 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以50%的产率得到N-(pyrimidin-4′-ylmethyl)-3,9-dioxa-6-azaundecane-1,11-diol
  参考文献：
  名称：

  Flavonoid Dimers as Novel, Potent Antileishmanial Agents

  摘要：

  The present study found that synthetic flavonoid dimers with either polyethylene glycol linker or amino ethyleneglycol linker have marked leishmanicidal activity. Compound 39 showed very consistent and promising leishmanicidal activity for both extracellular promastigotes (IC50 ranging from 0.13 to 0.21 mu M) and intracellular amastigotes (IC50 = 0.63 mu M) irrespective of the drug-sensitivity of parasites. Moreover, compound 39 displayed no toxicity toward macrophage RAW 264.7 cells (IC50 > 100 mu M) and primary mouse peritoneal elicited macrophages (IC50 > 88 mu M). Its high value of therapeutic index (> 140) was better than other highly potent antileishmanials such as amphotericin B (therapeutic index = 119). Compound 39 is therefore a new, safe, and effective antileishmanial candidate compound which is even effective against drug-refractory parasites.

  DOI：

  10.1021/jm301172v

文献信息

• Flavonoid Dimers as Novel, Potent Antileishmanial Agents
  作者：Iris L. K. Wong、Kin-Fai Chan、Tak Hang Chan、Larry M. C. Chow

  DOI：10.1021/jm301172v

  日期：2012.10.25

  The present study found that synthetic flavonoid dimers with either polyethylene glycol linker or amino ethyleneglycol linker have marked leishmanicidal activity. Compound 39 showed very consistent and promising leishmanicidal activity for both extracellular promastigotes (IC50 ranging from 0.13 to 0.21 mu M) and intracellular amastigotes (IC50 = 0.63 mu M) irrespective of the drug-sensitivity of parasites. Moreover, compound 39 displayed no toxicity toward macrophage RAW 264.7 cells (IC50 > 100 mu M) and primary mouse peritoneal elicited macrophages (IC50 > 88 mu M). Its high value of therapeutic index (> 140) was better than other highly potent antileishmanials such as amphotericin B (therapeutic index = 119). Compound 39 is therefore a new, safe, and effective antileishmanial candidate compound which is even effective against drug-refractory parasites.