1‐(2‐oxoethyl)‐5‐bromouracil | 18001-99-5

• 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‐oxoethyl)‐5‐bromouracil
• 英文别名: 2-(5-Bromo-2,4-dioxopyrimidin-1-yl)acetaldehyde
• CAS: 18001-99-5
• 化学式: C₆H₅BrN₂O₃
• 分子量: 233.021
• InChiKey: NFTUEXIMVFKZLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1‐(2‐oxoethyl)‐5‐bromouracil 在 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 9.0h， 生成 trans-5-bromo-1-((-5-(hydroxymethyl)-2-methylisoxazolidin-3-yl)methyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of novel isoxazolidine analogues of homonucleosides

  摘要：

  A general method for the synthesis of nucleobase-derived nitrones 4a-e by treatment of N-(2-oxoethyl)nucleobases with N-methylhydroxylamine is reported. The nitrones 4a-e were applied in the synthesis of isoxazolidine homonucleosides. Moderate diastereoselectivities (de 28-82%) were observed for cycloadditions between nitrones 4a-e and allyl alcohol with cis-isoxazolidines predominating. The stereochemistry of the substituted isoxazolidines was established based on an analysis of 2D NOE experiments for uracil-containing cycloadducts 6a and 7a. Cycloadditions of uracil-based nitrone 4a with vinyl-, allyl-, vinyloxymethyl- and allyloxymethylphosphonates gave the respective phosphonylated cis-isoxazolidines as the major adducts. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.074

文献信息

• Nucleobase-Derived Nitrones: Synthesis and Antioxidant and Neuroprotective Activities in an In Vitro Model of Ischemia–Reperfusion
  作者：Beatriz Chamorro、Iwona E. Głowacka、Joanna Gotkowska、Rafał Gulej、Dimitra Hadjipavlou-Litina、Francisco López-Muñoz、José Marco-Contelles、Dorota G. Piotrowska、María Jesús Oset-Gasque

  DOI：10.3390/ijms23063411

  日期：——

  -phenyl-N-tert-butylnitrone (PBN) and are similar to N-acetyl-L-cysteine (NAC), a well-known antioxidant and neuroprotective agent. The nitrones with the highest neuroprotective capacity were those containing purine nucleobases (nitrones 9f, g, B = adenine, theophylline), followed by nitrones with pyrimidine nucleobases with H or F substituents at the C5 position (nitrones 9a, c). All of these possess EC50 values

  在此，我们报告了一些命名为9a - i的核碱基衍生硝酮的合成、抗氧化和神经保护特性。使用人神经母细胞瘤 SH-SY5Y 细胞针对氧-葡萄糖剥夺体外缺血模型测量硝酮9a -i的神经保护特性。我们的结果表明，硝酮9a -i比 -苯基-N-叔丁基硝酮 ( PBN ) 具有更好的神经保护和抗氧化特性，并且类似于 N-乙酰基-L-半胱氨酸 ( NAC )，一种众所周知的抗氧化剂和神经保护剂代理人。具有最高神经保护能力的硝酮是那些含有嘌呤碱基的硝酮（硝酮9f、g、 B = 腺嘌呤，茶碱），然后是在 C5 位带有 H 或 F 取代基的嘧啶核碱基的硝酮（硝酮9a，c）。所有这些都具有 1-6 M 范围内的 EC 50值和高于 100% 的最大活性。然而，引入甲基取代基（硝酮9b， B = 胸腺嘧啶）或硬卤素取代基如 Br 和 Cl（分别为硝酮9 d，e ， B = 5-Br 和 5-Cl 尿嘧啶）会降低神经保护活性以尿嘧啶为核碱基的硝酮
• Synthesis of novel isoxazolidine analogues of homonucleosides
  作者：Joanna Gotkowska、Jan Balzarini、Dorota G. Piotrowska

  DOI：10.1016/j.tetlet.2012.10.074

  日期：2012.12

  A general method for the synthesis of nucleobase-derived nitrones 4a-e by treatment of N-(2-oxoethyl)nucleobases with N-methylhydroxylamine is reported. The nitrones 4a-e were applied in the synthesis of isoxazolidine homonucleosides. Moderate diastereoselectivities (de 28-82%) were observed for cycloadditions between nitrones 4a-e and allyl alcohol with cis-isoxazolidines predominating. The stereochemistry of the substituted isoxazolidines was established based on an analysis of 2D NOE experiments for uracil-containing cycloadducts 6a and 7a. Cycloadditions of uracil-based nitrone 4a with vinyl-, allyl-, vinyloxymethyl- and allyloxymethylphosphonates gave the respective phosphonylated cis-isoxazolidines as the major adducts. (C) 2012 Elsevier Ltd. All rights reserved.