Benzoic acid (1R,3R,4R,7S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-hydroxy-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester | 293751-31-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzoic acid (1R,3R,4R,7S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-hydroxy-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester
• 英文别名: [(1R,3R,4R,7S)-3-(2,4-dioxopyrimidin-1-yl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-1-yl]methyl benzoate
• CAS: 293751-31-2
• 化学式: C₁₇H₁₆N₂O₇
• 分子量: 360.323
• InChiKey: CCUGPYYYLDJQME-UMPJEAMMSA-N

物化性质

• 密度：
  1.527±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

制备方法与用途

5'-O-苯甲酰基-2'-O,4'-C-亚甲基尿苷是一种嘌呤核苷类似物，具有广泛的抗肿瘤活性，尤其针对惰性淋巴系统恶性肿瘤。其抗癌机制主要依赖于抑制DNA合成和诱导细胞凋亡等作用[1]。

反应信息

• 作为反应物：
  描述：

  Benzoic acid (1R,3R,4R,7S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-hydroxy-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester 在 吡啶 、 甲醇 、 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 5′-O-(4,4′-dimethoxytrityl)-2′-O,4′-C-methylenethymidine-3′-[O-(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite
  参考文献：
  名称：

  DNA triplex structures are stabilized by the incorporation of 3′-endo blocked pyrimidine nucleosides in the hoogsteen strand

  摘要：

  A short route to pyrimidine locked nucleosides has been developed for their incorporation in tripler forming oligonucleotides (TFO). Compared to oligonucleotides built with standard nucleosides, the modified TFOs containing 3'-endo blocked residues formed, with their corresponding DNA duplexes, more stable triple helix systems, an effect which might be ascribed to the 3'-endo pucker of the modified nucleoside residues. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00434-0
• 作为产物：
  描述：

  ((1R,3R,4R,7S)-7-([1,1'-biphenyl]-4-ylmethoxy)-3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate 在 iron(III) chloride 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以56%的产率得到Benzoic acid (1R,3R,4R,7S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-hydroxy-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester
  参考文献：
  名称：

  IMPROVED SYNTHESIS OF ¬2.2.1|BICYCLO NUCLEOSIDES

  摘要：

  公开号：

  EP1163250B1

文献信息

• IMPROVED SYNTHESIS OF ¬2.2.1|BICYCLO NUCLEOSIDES
  申请人：Exiqon A/S

  公开号：EP1163250B1

  公开（公告）日：2006-07-12
• DNA triplex structures are stabilized by the incorporation of 3′-endo blocked pyrimidine nucleosides in the hoogsteen strand
  作者：Pascal Savy、Rachid Benhida、Jean-Louis Fourrey、Rosalie Maurisse、Jian-Sheng Sun

  DOI：10.1016/s0960-894x(00)00434-0

  日期：2000.10

  A short route to pyrimidine locked nucleosides has been developed for their incorporation in tripler forming oligonucleotides (TFO). Compared to oligonucleotides built with standard nucleosides, the modified TFOs containing 3'-endo blocked residues formed, with their corresponding DNA duplexes, more stable triple helix systems, an effect which might be ascribed to the 3'-endo pucker of the modified nucleoside residues. (C) 2000 Elsevier Science Ltd. All rights reserved.