1-(3-bromo-2,3-dideoxy-β-D-threo-pentofuranosyl)-5-fluorouracil | 1227358-28-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(3-bromo-2,3-dideoxy-β-D-threo-pentofuranosyl)-5-fluorouracil
• 英文别名: 1-[(2R,4R,5R)-4-bromo-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-fluoro-pyrimidine-2,4-dione；1-[(2R,4R,5R)-4-bromo-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidine-2,4-dione
• CAS: 1227358-28-2
• 化学式: C₉H₁₀BrFN₂O₄
• 分子量: 309.092
• InChiKey: TZAOSPUOPDCJLV-QPPQHZFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3-bromo-2,3-dideoxy-β-D-threo-pentofuranosyl)-5-fluorouracil 在 dipotassium peroxodisulfate 、 ruthenium(III) chloride trihydrate 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 8.0h， 以67%的产率得到1-(3,4-didehydro-2,3-dideoxy-5-oxo-β-D-pentofuranosyl)-5-fluorouracil
  参考文献：
  名称：

  4'-Modified Pyrimidine Nucleosides as Potential Anti-hepatitis C Virus (HCV) Agents

  摘要：

  在此，我们研究了具有 4'- 羧基官能团的新型嘧啶核苷（6-10、13 和 15）作为抗HCV 药物。在这一类新化合物中，7、9、10 和 15 的体外抗HCV 活性类似于或优于已知的抗HCV 药物利巴韦林。在这项工作中，我们还意外地发现了一种 3'-thiacytidine 的 3'-sulfoxide 类似物（16），它是在合成 15 的过程中作为副产品获得的，是一种有效的 HCV 复制抑制剂，其浓度与利巴韦林相似。在测试的最高浓度范围内，未发现所研究化合物具有可检测到的体外细胞毒性。

  DOI：

  10.2174/1570180811666140401184856
• 作为产物：
  描述：

  5'-O-trityl-3'-O-mesyl-2'-deoxy-5-fluorouridine 在 lithium bromide 作用下， 以 乙腈 为溶剂， 反应 22.0h， 以24%的产率得到1-(3-bromo-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-fluorouracil
  参考文献：
  名称：

  3′-Bromo Analogues of Pyrimidine Nucleosides as a New Class of Potent Inhibitors ofMycobacterium tuberculosis

  摘要：

  Tuberculosis (TB) is a major health problem worldwide. We herein report a new class of pyrimidine nucleosides as potent inhibitors of Mycobacterium tuberculosis (M. tuberculosis). Various 2'- or 3'-halogeno derivatives of pyrimidine nucleosides containing uracil, 5-fluorouracil, and thymine bases were synthesized and evaluated for antimycobacterial activities. Among the compounds tested, 3'-bromo-3'-deoxy-arabinofuranosylthymine (3') was the most effective antituberculosis agent in the in vitro assays against wild-type M. tuberculosis strain (H37Ra) (MIC50 = 1 mu g/mL) as well as drug-resistant (H37Rv) (rifampicin-resistant and isoniazid-resistant) strains of M. tuberculosis (MIC50 = 1-2 mu g/mL). Compound 3' also inhibited intracellular M. tuberculosis in a human monocytic cell line infected with H37Ra, demonstrating higher activity against intramacrophagic mycobacteria (80% reduction at 10 mu g/mL concentration) than extracellular mycobacteria (75% reduction at 10 mu g/mL concentration). In contrast, pyrimidine nucleosides possessing 5-fluorouracil base were weak inhibitors of M. tuberculosis. No cytotoxicity was found up to the highest concentration of compounds tested (CC50 > 100-200 mu g/mL) against a human cell line. Overall, these encouraging results substantiate the potential of this new class of compounds as promising antituberculosis agents.

  DOI：

  10.1021/jm100165w