5'-azido-5'-deoxy-5-fluoro-2',3'-O-isopropylideneuridine | 82207-45-2

• 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: 5'-azido-5'-deoxy-5-fluoro-2',3'-O-isopropylideneuridine
• 英文别名: 5'-deoxy-5'-azido-2',3'-O-isopropylidene-5-fluorouridine
• CAS: 82207-45-2
• 化学式: C₁₂H₁₄FN₅O₅
• 分子量: 327.272
• InChiKey: KBINNRXZQDTAIZ-FDDDBJFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  131.31
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5'-azido-5'-deoxy-5-fluoro-2',3'-O-isopropylideneuridine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Squaryl group-modified UDP analogs as inhibitors of the endoplasmic reticulum-resident folding sensor enzyme UGGT

  摘要：

  UDP-Glc：糖蛋白葡萄糖基转移酶（UGGT）在内质网（ER）中具有中心作用，以保持正确折叠的N-糖基蛋白的质量控制。

  DOI：

  10.1039/d2cc06634c
• 作为产物：
  描述：

  5-fluoro-2',3'-O-isopropylidene-5'-O-(p-toluenesulfonyl)uridine 在 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以73%的产率得到5'-azido-5'-deoxy-5-fluoro-2',3'-O-isopropylideneuridine
  参考文献：
  名称：

  潜在的5-氟尿嘧啶前药的合成及其体内抗肿瘤活性。

  摘要：

  DOI：

  10.1021/jm00351a006

文献信息

• Synthesis of α‐Hydroxy‐1,2,3‐Triazole‐linked Sialyltransferase Inhibitors and Evaluation of Selectivity Towards ST3GAL1, ST6GAL1 and ST8SIA2
  作者：Rémi Szabo、Chris Dobie、Andrew P. Montgomery、Harrison Steele、Haibo Yu、Danielle Skropeta

  DOI：10.1002/cmdc.202400088

  日期：2024.8.19

  into 1,2,3-triazole linked sialyltransferase inhibitors, we present the design and synthesis of a new series of compounds that improve upon the drug-likeness of the parent scaffold. Additionally, we performed a preliminary SAR study with the STs hST3GAL1, hST6GAL1, and hST8SIA2. This work provides new insights into the design of selective ST inhibitors, particularly considering different nucleoside

  基于我们之前对 1,2,3-三唑连接的唾液酸转移酶抑制剂的研究，我们提出了一系列新化合物的设计和合成，这些化合物改进了母体支架的药物相似性。此外，我们还使用 STs hST3GAL1 、 hST6GAL1 和 hST8SIA2 进行了初步 SAR 研究。这项工作为选择性 ST 抑制剂的设计提供了新的见解，特别是考虑了不同的核苷衍生物。
• Synthesis and biological activity of 5'-substituted 5-fluoropyrimidine nucleosides
  作者：Sudhir Ajmera、Peter V. Danenberg

  DOI：10.1021/jm00350a024

  日期：1982.8

  5'-Deoxy-5-fluorouridine (5'-dFUrd, 1) possesses a significantly higher chemotherapeutic index than other fluoropyrimidines as a result of its being selectivity cleaved in tumors to 5-fluorouracil (FUra) by uridine phosphorylase. Because 1 is a relatively poor substrate for this enzyme, we synthesized a series of 5'-deoxy-5'-substituted-5-fluorouridine (FUrd) derivatives in an effort to obtain compounds that might have improved substrate interactions compared to 1 and thus possibly be better prodrugs of FUra. Three derivatives, 5'-O-tosyl-FUrd (13), 5'-O-mesyl-FUrd (14), and 5'-deoxy-5'-bromo-FUrd (15), had cytostatic activity against L1210 and CCRF-CEM leukemic cells in culture superior to that of 1. In preliminary in vivo antitumor studies against L1210 leukemic cells in mice, 5'-deoxy-5'-chloro-FUrd (4), 5'-O-mesyl-FUrd (14), an 5'-deoxy-5'-fluoro-FUrd (18) gave percent increases in life span of 64, 58, and 58, respectively, compared to a value of 20 for compound 1.