1,3-bis(5-bromopentyl)thymine | 197300-61-1

• 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(5-bromopentyl)thymine
• 英文别名: Bis(5 bromopentyl)thymine；1,3-bis(5-bromopentyl)-5-methylpyrimidine-2,4-dione
• CAS: 197300-61-1
• 化学式: C₁₅H₂₄Br₂N₂O₂
• 分子量: 424.176
• InChiKey: LMSXCHJBJHFGEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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(5-bromopentyl)thymine 在 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 31.5h， 生成 15-methyl-7-butyl-7-n-decyl-1,7,13-triazabicyclo[11.3.1]heptadeca-15-en-14,17-dione bromide
  参考文献：
  名称：

  Antibacterial and antifungal activity of acyclic and macrocyclic uracil derivatives with quaternized nitrogen atoms in spacers

  摘要：

  The reactions of 1,3-bis(alpha,omega-bromoalkyl)-6-methyluracils with 1,3-bis(alpha,omega-ethylaminoalkyl)-6-methyluracils or 1,3-bis(bromopentyl)thymine with butylamine afforded pyrimidinophanes containing one or two uracil units and nitrogen atoms in bridging polymethylene chains. In some cases individual geometric isomers of pyrimidinophanes differing in the mutual arrangement of the carbonyl and methyl groups at different pyrimidine rings were isolated. Quaternization of the bridging nitrogen atom with o-nitrobenzyl bromide, benzyl bromide, n-decyl bromide gave rise to water-soluble pyrimidinophanes which were evaluated for their antibacterial and antifungal activity. The arrangement of the carbonyl groups in macrocycles doesn't affect the activity. Antibacterial and antifungal activity of pyrimidinophanes increases with the increase of polymethylene N-(pyr)-N-chain length and dramatically increases upon the introduction of n-decyl substituent at nitrogen atoms in spacers. Pyrimidi-nophanes with 5 and 6 methylene groups in N(pyr)-N-chain and n-decyl substituent showed significant bacteriostatic, fungistatic, bactericidal, fungicidal activity which comparable with standard antibacterial and antifungal drugs. Acyclic counterpart demonstrated the highest activity against fungi. Toxicity of more effective pyrimidinophanes was determined for mice and Daphnia magna Straus. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.03.030
• 作为产物：
  描述：

  1,5-二溴戊烷 、 thymine disodium salt 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以45%的产率得到1,3-bis(5-bromopentyl)thymine
  参考文献：
  名称：

  Synthesis and structures of pyrimidinophanes containing a nitrogen atom in the bridge

  摘要：

  1,3-双(5-溴戊基)-5-甲基-或1,3-双(5-溴戊基)-6-甲基-尿嘧啶与苄胺的反应产生了嘧啶并环，其中氮原子位于聚亚甲基桥上。单晶X射线衍射研究以及溶液中的核磁共振和紫外光谱研究证明，大环中的苯基和尿嘧啶片段在空间上接近。与已知的大环含有嘧啶环不同，正在研究的嘧啶并环在构象上是刚性的。

  DOI：

  10.1007/s11172-006-0292-1

文献信息

• NMR and UV Study of 1,1′-(<i>α</i>,<i>ω</i>-Alkanediyl)bis[thymine] and 1,1′-(<i>α</i>,<i>ω</i>-Alkanediyl)bis[uracil]
  作者：Toshio Itahara

  DOI：10.1246/bcsj.70.2239

  日期：1997.9

  Treatment of thymine or uracil with Br(CH2)nBr (n = 3—10) in the presence of t-BuOK gave 1,1′-(α,ω-alkanediyl)bis[thymine] or 1,1′-(α,ω-alkanediyl)bis[uracil] together with 1-(ω-bromoalkyl)thymine or 1-(ω-bromoalkyl)uracil. The structures of these products were determined on the basis of the coupling constants between 5- and 3-positions of uracil ring on the 1H NMR spectra. Molecular aggregation of the thymine and uracil rings of these compounds in aqueous solution was studied on the basis of their 1H NMR and UV spectra. A stacking interaction of the two thymine rings linked by shorter polymethylene chains such as trimethylene and tetramenthylene groups was observed.

  将胸腺嘧啶或尿嘧啶与Br(CH2)nBr（n = 3—10）在t-BuOK存在下处理，得到了1,1′-(α,ω-烷烃二基)双[胸腺嘧啶]或1,1′-(α,ω-烷烃二基)双[尿嘧啶]，以及1-(ω-溴烷基)胸腺嘧啶或1-(ω-溴烷基)尿嘧啶。这些产物的结构是基于尿嘧啶环中5位和3位之间的耦合常数在1H NMR光谱上的分析来确定的。基于它们的1H NMR和紫外光谱，研究了这些化合物在水溶液中胸腺嘧啶和尿嘧啶环的分子聚集情况。观察到由较短的聚亚 methylene 链（如三亚甲基和四亚甲基基团）连接的两个胸腺嘧啶环之间存在堆叠相互作用。
• Unusual Reaction of Macrocyclic Uracils with Paraformaldehyde
  作者：Vyacheslav E. Semenov、Rashit Kh. Giniyatullin、Anatoly S. Mikhailov、Anton E. Nikolaev、Sergey V. Kharlamov、Shamil K. Latypov、Vladimir S. Reznik

  DOI：10.1002/ejoc.201100985

  日期：2011.10

  The ability of simple uracils to afford bis(uracil-5-yl)methanes upon reaction with paraformaldehyde is well documented. This reaction has been used in the preparation of pyrimidinophanes. The extension of the scope of this reaction to the synthesis of multipyrimidinophanes has been reported. Starting with isomeric pyrimidinophane containing 6-methyluracil and 5-methyluracil (thymine) moieties, linearly

  简单的尿嘧啶在与多聚甲醛反应后提供双（尿嘧啶-5-基）甲烷的能力已得到充分证明。该反应已用于制备嘧啶烷。已报道将该反应的范围扩展到多嘧啶烷的合成。以含有 6-甲基尿嘧啶和 5-甲基尿嘧啶（胸腺嘧啶）部分的异构嘧啶并烷为起始，制备了线性排列的多大环。一个完全出乎意料的结果是，含有 6-甲基尿嘧啶部分的异构嘧啶烷与多聚甲醛的反应仅产生环状排列的大环，特别是具有环状拓扑结构的穴状嘧啶和多嘧啶。
• Synthesis and structures of pyrimidinophanes containing a nitrogen atom in the bridge
  作者：V. E. Semenov、A. E. Nikolaev、L. F. Galiullina、O. A. Lodochnikova、I. A. Litvinov、A. P. Timosheva、V. E. Kataev、Yu. Ya. Efremov、D. R. Sharafutdinova、A. V. Chernova、Sh. K. Latypov、V. S. Reznik

  DOI：10.1007/s11172-006-0292-1

  日期：2006.3

  The reactions of 1,3-bis(5-bromopentyl)-5-methyl-or 1,3-bis(5-bromopentyl)-6-methyl-uracil with benzylamine afforded pyrimidinophanes containing the nitrogen atom in the polymethylene bridge. Single-crystal X-ray diffraction study and NMR and UV spectroscopic study in solution demonstrated that the phenyl and uracil fragments in the macrocycles are in spatial proximity. Unlike the known macrocycles containing the pyrimidine ring, the pyrimidinophanes under study are conformationally rigid.

  1,3-双(5-溴戊基)-5-甲基-或1,3-双(5-溴戊基)-6-甲基-尿嘧啶与苄胺的反应产生了嘧啶并环，其中氮原子位于聚亚甲基桥上。单晶X射线衍射研究以及溶液中的核磁共振和紫外光谱研究证明，大环中的苯基和尿嘧啶片段在空间上接近。与已知的大环含有嘧啶环不同，正在研究的嘧啶并环在构象上是刚性的。
• Synthesis of pyrimidinocyclophanes having a bridging nitrogen atom
  作者：V. E. Semenov、A. E. Nikolaev、A. V. Kozlov、Yu. Ya. Efremov、Sh. K. Latypov、V. S. Reznik

  DOI：10.1134/s1070428008060183

  日期：2008.6

  Reactions of 1,3-bis(omega-bromoalkyl)-substituted uracils, quinazoline-2,4-dione, and 5-methyl-1,3,5-triazine-2,4,6-trione and 1,3-bis(m-bromomethylbenzyl)-5-bromouracil with amines (aliphatic amines, benzylamines, naphthylmethanamine, and anisidine) gave a series of macrocyclic compounds having one pyrimidine or triazine fragment and an azapolymethylene bridge connecting the N-1 and N-3 atoms of the heteroring. The bridging nitrogen atom in some macrocyclic compounds was subjected to quaternization with methyl p-toluenesulfonate.
• 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.