1,3-bis[4-(4-dimethylamino-6-methylpyrimidin-2-ylthio)hexyl]-6-methyluracil | 802976-89-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,3-bis[4-(4-dimethylamino-6-methylpyrimidin-2-ylthio)hexyl]-6-methyluracil
• 英文别名: 1,3-Bis[6-[4-(dimethylamino)-6-methylpyrimidin-2-yl]sulfanylhexyl]-6-methylpyrimidine-2,4-dione
• CAS: 802976-89-2
• 化学式: C₃₁H₄₈N₈O₂S₂
• 分子量: 628.907
• InChiKey: HYDJQVVNRBQRCO-UHFFFAOYSA-N

物化性质

• 沸点：
  769.3±70.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  43
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,3-bis[4-(4-dimethylamino-6-methylpyrimidin-2-ylthio)hexyl]-6-methyluracil 、 对甲苯磺酸甲酯 反应 7.0h， 以97%的产率得到
  参考文献：
  名称：

  Antimicrobial activity of pyrimidinophanes with thiocytosine and uracil moieties

  摘要：

  Reactions of pyrimidinophanes with two 6-methylthiocytosine and one 5(6)-alkyluracil moieties bridged with each other by polymethylene spacers with methyl or nonyl p-toluenesulfonate, p-toluenesulfonic acid, methanesulfonate and trifluorosulfonate afforded amphiphilic macrocyclic bis-p-toluene-, methane- and trifluorosulfonates. Despite the presence of several reaction centers in the initial pyrimidinophane molecules, protonation and methylation occurred only at the N-1 atom (with quaternization) of the 6-methylthiocytosine moieties. The bacteriostatic and fungistatic activity of the products was estimated. Macrocyclic tosylates exhibit a remarkable selectivity towards Staphylococcus aureus, with MIC values comparable with a reference drug. Bacteriostatic activity of the amphiphilic pyrimiclinophanes depends on the size of the macrocycles, and the highest activity corresponds to definite lengths of polymethylene bridges. Besides, the antimicrobial activity of the screened pyrimidine derivatives depends on their topology. While macrocyclic tosylates are more active against bacteria than against fungi, acyclic tosylate with the same structural fragments shows a dramatical decrease of MIC towards mold and yeast with respect to the corresponding macrocycle. It is found that macrocyclic and acyclic tosylates in high dilutions decrease the extracellular lipase activity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.034
• 作为产物：
  描述：

  1,3-bis(6-bromohexyl)-6-methyluracil 、 4-(N,N-dimethylamino)-2-mercapto-6-methylpyrimidine sodium salt 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以86%的产率得到1,3-bis[4-(4-dimethylamino-6-methylpyrimidin-2-ylthio)hexyl]-6-methyluracil
  参考文献：
  名称：

  Antimicrobial activity of pyrimidinophanes with thiocytosine and uracil moieties

  摘要：

  Reactions of pyrimidinophanes with two 6-methylthiocytosine and one 5(6)-alkyluracil moieties bridged with each other by polymethylene spacers with methyl or nonyl p-toluenesulfonate, p-toluenesulfonic acid, methanesulfonate and trifluorosulfonate afforded amphiphilic macrocyclic bis-p-toluene-, methane- and trifluorosulfonates. Despite the presence of several reaction centers in the initial pyrimidinophane molecules, protonation and methylation occurred only at the N-1 atom (with quaternization) of the 6-methylthiocytosine moieties. The bacteriostatic and fungistatic activity of the products was estimated. Macrocyclic tosylates exhibit a remarkable selectivity towards Staphylococcus aureus, with MIC values comparable with a reference drug. Bacteriostatic activity of the amphiphilic pyrimiclinophanes depends on the size of the macrocycles, and the highest activity corresponds to definite lengths of polymethylene bridges. Besides, the antimicrobial activity of the screened pyrimidine derivatives depends on their topology. While macrocyclic tosylates are more active against bacteria than against fungi, acyclic tosylate with the same structural fragments shows a dramatical decrease of MIC towards mold and yeast with respect to the corresponding macrocycle. It is found that macrocyclic and acyclic tosylates in high dilutions decrease the extracellular lipase activity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.034

文献信息

• Metal binding properties of pyrimidinophanes and their acyclic counterparts
  作者：Sergey N. Podyachev、Vyacheslav E. Semenov、Victor V. Syakaev、Nadezda E. Kashapova、Svetlana N. Sudakova、Julia K. Voronina、Anatoly S. Mikhailov、Alexandra D. Voloshina、Vladimir S. Reznik、Alexander I. Konovalov

  DOI：10.1039/c3ra47571a

  日期：——

  A series of acyclic and macrocyclic nucleobase derivatives that contain uracil and 2-thiocytosine units linked by polymethylene spacers was prepared. The length of spacers as well as the oxidation number of sulfur atoms entering into the structure of the compounds was varied. The crystal structure of pyrimidinophane with hexa- and heptamethylene linkers was established by X-ray analysis. The metal ion-binding properties of pyrimidinophanes and their acyclic counterparts were investigated by liquid extraction and 1H NMR titration experiments. The compounds with 2-thiocytosine fragments revealed a high selectivity of extraction towards Ag+ ions. The stoichiometry of silver complexes and the binding constants have been determined. The antibacterial activity of these complexes was also discussed.

  一系列含有尿嘧啶和2-硫胞嘧啶单元并通过聚亚甲基间隔相连的非环和宏环核碱衍生物被制备出来。间隔的长度以及进入化合物结构的硫原子的氧化数被改变。通过X射线分析确定了含有六亚甲基和七亚甲基连接体的嘧啶冠醚的晶体结构。通过液体萃取和1H NMR滴定实验研究了嘧啶冠醚及其非环对应物的金属离子结合性质。含有2-硫胞嘧啶片段的化合物显示出对Ag+离子的高选择性萃取。确定银络合物的化学计量比和结合常数。这些络合物的抗菌活性也进行了讨论。