1-(2-hydroxy-3-methoxypropyl)-5-bromouracil

• 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-(2-hydroxy-3-methoxypropyl)-5-bromouracil
• 英文别名: 5-Bromo-1-(2-hydroxy-3-methoxypropyl)uracil；5-Bromo-1-(2-hydroxy-3-methoxypropyl)pyrimidine-2,4-dione
• 化学式: C₈H₁₁BrN₂O₄
• 分子量: 279.09
• InChiKey: VFFDATOUDAOMEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (甲氧基甲基)环氧乙烷 、 5-溴尿嘧啶 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以52%的产率得到1-(2-hydroxy-3-methoxypropyl)-5-bromouracil
  参考文献：
  名称：

  SYNTHESIS OF 1-(2-HYDROXY-3-METHOXYPROPYL)URACILS AND THEIR ACTIVITY AGAINST L1210 AND MACROPHAGE RAW 264.7 CELLS

  摘要：

  The title compounds were obtained from appropriate 5-substituted uracil derivatives and 1,2-oxy-3-methoxypropane in the presence of sodium hydride. Under similar conditions 5-iodouracil gave 2-methoxymethyl-2,3-dihydro-oxazolo[3,2-c]pyrimidine-5,7-dione as a result of intramolecular cine type nucleophilic substitution. Cytotoxicity of 1(2-hydroxy-3-methoxypropyl)-5-substituted uracil derivatives against L1210 and macrophage RAW 264.7 cells in vitro was examined.

  DOI：

  10.1081/ncn-120006831

文献信息

• Salts of 5-Substituted Uracils with 1,8-Diazabicyclo[5.4.0]-undec-7-ene: Convenient Reagents for Nucleophilic Addition and Substitution Reactions
  作者：Jerzy Suwiński、Krzysztof Walczak

  DOI：10.1055/s-2001-10805

  日期：——

  1,8-Diazabicyclo[5.4.0]-undec-7-ene (DBU) salts of 5-substituted uracils have been obtained as crystals. The salts were used as nucleophiles in the synthesis of 1-(2′-hydroxy-3′-methoxypropyl)uracils by oxirane ring opening in 1,2-epoxy-3-methoxypropane and in reversed pyrimidine nucleosides synthesis by substitution of the terminal tosylate group in methyl 6-O-tosyl-α-d-glucopyranoside.

  1,8-二氮双环[5.4.0]癸-7-烯（DBU）盐类的5-取代尿嘧啶已被获得为晶体。这些盐被用作亲核试剂，通过在1,2-环氧-3-甲氧基丙烷中开环反应合成1-(2′-羟基-3′-甲氧基丙基)尿嘧啶，并通过取代甲基6-O-托烯基-α-d-葡萄糖苷中的末端托烯基团合成逆向嘧啶核苷。
• SYNTHESIS OF 1-(2-HYDROXY-3-METHOXYPROPYL)URACILS AND THEIR ACTIVITY AGAINST L1210 AND MACROPHAGE RAW 264.7 CELLS
  作者：Alicja Copik、Jerzy Suwinski、Krzysztof Walczak、Joanna Bronikowska、Zenon Czuba、Wojciech Król

  DOI：10.1081/ncn-120006831

  日期：2002.7

  The title compounds were obtained from appropriate 5-substituted uracil derivatives and 1,2-oxy-3-methoxypropane in the presence of sodium hydride. Under similar conditions 5-iodouracil gave 2-methoxymethyl-2,3-dihydro-oxazolo[3,2-c]pyrimidine-5,7-dione as a result of intramolecular cine type nucleophilic substitution. Cytotoxicity of 1(2-hydroxy-3-methoxypropyl)-5-substituted uracil derivatives against L1210 and macrophage RAW 264.7 cells in vitro was examined.