1-(5-bromouracil-1-yl)-1,2-dideoxy-β-D-erythro-pentofuranuronic acid | 3180-31-2

• 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-(5-bromouracil-1-yl)-1,2-dideoxy-β-D-erythro-pentofuranuronic acid
• 英文别名: (2S,3S,5R)-5-(5-bromo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-carboxylic acid；(2S,3S,5R)-5-(5-bromo-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolane-2-carboxylic acid
• CAS: 3180-31-2
• 化学式: C₉H₉BrN₂O₆
• 分子量: 321.084
• InChiKey: VBAJOLXYSGEAGD-JKUQZMGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(5-bromouracil-1-yl)-1,2-dideoxy-β-D-erythro-pentofuranuronic acid 在 二苯基磷酸 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  Synthesis of a Carboxamide Linked U^Br∗U^BrDimer–Duplex and Triplex Stabilities of the Corresponding Oligodeoxynucleotides

  摘要：

  A U-Br*U-Br dimer was synthesized by connecting the appropiate nucleoside monomers through a 5-atom carboxamide linkage. The dimer was incorporated in oligodeoxynucleotides and investigated for hybridization properties toward single and double stranded DNA.

  DOI：

  10.1080/15257779508010721
• 作为产物：
  描述：

  溴脲苷 在 platinum(IV) oxide 氧气 作用下， 以 水 为溶剂， 反应 8.0h， 以85%的产率得到1-(5-bromouracil-1-yl)-1,2-dideoxy-β-D-erythro-pentofuranuronic acid
  参考文献：
  名称：

  Synthesis of a Carboxamide Linked U^Br∗U^BrDimer–Duplex and Triplex Stabilities of the Corresponding Oligodeoxynucleotides

  摘要：

  A U-Br*U-Br dimer was synthesized by connecting the appropiate nucleoside monomers through a 5-atom carboxamide linkage. The dimer was incorporated in oligodeoxynucleotides and investigated for hybridization properties toward single and double stranded DNA.

  DOI：

  10.1080/15257779508010721

文献信息

• Evaluation of Oligonucleotides with Novel Modifications
  作者：Erik Larsen、Krzysztof Danel、Abdel-Aleem Abdel-Aleem、Poul Niclsen、Jesper Wengel、Erik Pedersen

  DOI：10.1080/15257779508012543

  日期：1995.5.1

  Oligodeoxynucleotides modified with carboxamide linked dimeric nucleotides and an acyclic nucleoside were prepared and investigated for their hybridization properties toward DNA.
• CYCLOPENTENE-OXYMETHYLENE PHOSPHONAMIDATES AND RELATED COMPOUNDS AND THEIR USE IN TREATING MEDICAL CONDITIONS
  申请人：[en]ROME THERAPEUTICS, INC.

  公开号：WO2024107859A1

  公开（公告）日：2024-05-23

  Substituted cyclopentene-oxymethylene phosphonamidates and related compounds, pharmaceutical compositions, their use for inhibiting LINE1 reverse transcriptase and/or HERV- K reverse transcriptase activity, and their use in the treatment of medical disorders, such as cancer, are disclosed herein.
• Synthesis of a Carboxamide Linked U^Br∗U^BrDimer–Duplex and Triplex Stabilities of the Corresponding Oligodeoxynucleotides
  作者：Abdel Aleem H. Abdel Aleem、Erik Larsen、Erik B. Pedersen

  DOI：10.1080/15257779508010721

  日期：1995.11

  A U-Br*U-Br dimer was synthesized by connecting the appropiate nucleoside monomers through a 5-atom carboxamide linkage. The dimer was incorporated in oligodeoxynucleotides and investigated for hybridization properties toward single and double stranded DNA.