1-(2'-deoxy-2'-fluoro-β-D-ribofuranosyl)-4-thiouracil | 10212-16-5

• 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-(2'-deoxy-2'-fluoro-β-D-ribofuranosyl)-4-thiouracil
• 英文别名: 2'-fluoro-4-thio-2'-deoxy-uridine；2'-Deoxy-2'-fluoro-4-thiouridine；1-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-sulfanylidenepyrimidin-2-one
• CAS: 10212-16-5
• 化学式: C₉H₁₁FN₂O₄S
• 分子量: 262.262
• InChiKey: LBXPACVSMLWUMQ-XVFCMESISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 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：
  114
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 储存条件：
  2-8°C

制备方法与用途

2′-脱氧-2′-氟-4-硫尿苷是一种嘌呤核苷类似物，具有广泛的抗肿瘤活性，特别针对惰性淋巴系统恶性肿瘤。其抗癌机制主要通过抑制DNA合成和诱导细胞凋亡来实现。

反应信息

• 作为产物：
  描述：

  2'-氟-2'-脱氧尿苷 在 劳森试剂 、 吡啶 、 氨 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 29.0h， 生成 1-(2'-deoxy-2'-fluoro-β-D-ribofuranosyl)-4-thiouracil
  参考文献：
  名称：

  Growth Inhibition of Mycobacterium bovis, Mycobacterium tuberculosis and Mycobacterium avium In Vitro:  Effect of 1-β-d-2‘-Arabinofuranosyl and 1-(2‘-Deoxy-2‘-fluoro-β-d-2‘-ribofuranosyl) Pyrimidine Nucleoside Analogs

  摘要：

  The resurgence of tuberculosis and the emergence of multiple-drug-resistant strains of Mycobacteria necessitate the search for new classes of antimycobacterial agents. We synthesized a series of 1-beta-D-2'-arabinofuranosyl and 1-(2'-deoxy-2'-fluoro-beta-D-ribofuranosyl) pyrimidine nucleosides possessing diverse sets of alkynyl, alkenyl, alkyl, and halo substituents at the C-5 position of the uracil and investigated their effect on activity against M. tuberculosis, M. bovis, and M. avium. Among these molecules, 5-alkynyl-substituted derivatives emerged as potent inhibitors of M. bovis, M. tuberculosis, and M. avium. Nucleosides 1-beta-D-2'-arabinofuranosyl-5-dodecynyluracil (5), 1-(2'-deoxy-2'-fluoro-beta-D-ribofuranosyl)-5-dodecynyluracil (24), and 1-(2'-deoxy-2'-fluoro-beta-D-ribofuranosyl)-5-tetradecynyluracil (25) showed the highest antimycobacterial potency against M. bovis and M. tuberculosis. The MIC90 exhibited by compounds 5,24, and 25 was similar or close to that of the reference drug rifampicin. The most active compounds 5, 24, and 25 were also found to retain sensitivity against a rifampicin-resistant strain of M. tuberculosis H37Rv at similar concentrations. Some of these analogs also revealed in vitro antimicrobial effect against several other gram-positive pathogens.

  DOI：

  10.1021/jm0703901