1,3-bis(ω-bromopropyl)-6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine | 60316-20-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1,3-bis(ω-bromopropyl)-6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine
• 英文别名: 1,3-bis(γ-bromopropyl)-6-methyluracil；1,3-bis-(3-bromo-propyl)-6-methyl-1H-pyrimidine-2,4-dione；1,3-Bis(3-bromopropyl)-6-methylpyrimidine-2,4-dione
• CAS: 60316-20-3
• 化学式: C₁₁H₁₆Br₂N₂O₂
• 分子量: 368.068
• InChiKey: JAVQABAZEXLFKH-UHFFFAOYSA-N

物化性质

• 沸点：
  411.2±55.0 °C(Predicted)
• 密度：
  1.618±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-bis(ω-bromopropyl)-6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine 在 sodium tetrahydroborate 、 氯化亚砜 、 sodium methylate 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 19.67h， 生成 1,3-bis[ω-(2-chloromethylphenoxy)propyl]-6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine
  参考文献：
  名称：

  Fattakhov; Solov'eva; Reznik, Russian Journal of General Chemistry, 2000, vol. 70, # 3, p. 461 - 468

  摘要：

  DOI：
• 作为产物：
  描述：

  6-甲基尿嘧啶 以15%的产率得到
  参考文献：
  名称：

  REZNIK V. S.; SALIXOV I. SH.; SHVETSOV YU. S.; SHIRSHOV A. N.; BAKULIN V.+, IZV. AN CCCP. CEP. XIM., 1977, HO 4, 880-884

  摘要：

  DOI：

文献信息

• Novel Uracil-Based Inhibitors of Acetylcholinesterase with Potency for Treating Memory Impairment in an Animal Model of Alzheimer’s Disease
  作者：Vyacheslav E. Semenov、Irina V. Zueva、Sofya V. Lushchekina、Eduard G. Suleimanov、Liliya M. Gubaidullina、Marina M. Shulaeva、Oksana A. Lenina、Konstantin A. Petrov

  DOI：10.3390/molecules27227855

  日期：——

  Novel derivatives based on 6-methyluracil and condensed uracil, 2,4-quinazoline-2,4-dione, were synthesized with terminal meta- and para-benzoate moieties in polymethylene chains at the N atoms of the pyrimidine ring. In the synthesized compounds, the polymethylene chains were varied from having tris- to hexamethylene chains and quaternary ammonium groups; varying substituents (ester, salt, acid) at

  基于 6-甲基尿嘧啶和缩合尿嘧啶 2,4-喹唑啉-2,4-二酮的新型衍生物在嘧啶环的 N 原子处的聚亚甲基链中合成了末端间苯甲酸酯和对苯甲酸酯部分。在合成的化合物中，多亚甲基链从具有三亚甲基链到六亚甲基链和季铵基团不等；苯环上的不同取代基（酯、盐、酸）被引入链和苯甲酸酯部分。体内生物学实验证明了这些化合物在减少 β-淀粉样斑块数量方面的效力及其在阿尔茨海默病转基因模型中治疗记忆障碍的适用性。
• Antimicrobial activity of pyrimidinophanes with thiocytosine and uracil moieties
  作者：Vyacheslav E. Semenov、Anatoly S. Mikhailov、Alexandra D. Voloshina、Natalia V. Kulik、Alexandra D. Nikitashina、Vladimir V. Zobov、Sergey V. Kharlamov、Shamil K. Latypov、Vladimir S. Reznik

  DOI：10.1016/j.ejmech.2011.05.034

  日期：2011.9

  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.
• Reaction of Na salts of some hydroxypyrimidines with ?, ?-dibromoalkanes
  作者：V. S. Reznik、I. Sh. Salikhov、Yu. S. Shvetsov、B. E. Ivanov

  DOI：10.1007/bf00949232

  日期：1980.11
• Synthesis and properties of pyrimidinylalkylsulfonamides
  作者：Yu. S. Shvetsov、V. D. Cherepinskii-Malov、A. N. Shirshov、V. S. Reznik、V. G. Andrianov

  DOI：10.1007/bf00951234

  日期：1980.10
• SHVETSOV YU. S.; CHEREPINSKIJ-MALOV V. D.; SHIRSHOV A. N.; REZNIK V. S.; +, IZV. AN CCCP. CEP. XIM., 1980, HO 10, 2356-2363
  作者：SHVETSOV YU. S.、 CHEREPINSKIJ-MALOV V. D.、 SHIRSHOV A. N.、 REZNIK V. S.、 +

  DOI：——

  日期：——