5-fluoro-1-(4-thio-α-D-arabinofuranosyl)cytosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 5-fluoro-1-(4-thio-α-D-arabinofuranosyl)cytosine
• 英文别名: 4-amino-1-[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)thiolan-2-yl]-5-fluoropyrimidin-2-one
• 化学式: C₉H₁₂FN₃O₄S
• 分子量: 277.276
• InChiKey: QDVOFRWTPUEFTR-NRFSWKIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  145
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  氟胞嘧啶 、 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-D-arabinofuranose 在 三甲基氯硅烷 、 六甲基二硅氮烷 、 三氟甲磺酸三甲基硅酯 、 三氯化硼 作用下， 以 乙腈 、 二氯甲烷 为溶剂， 反应 0.5h， 以50 mg的产率得到5-fluoro-1-(4-thio-α-D-arabinofuranosyl)cytosine
  参考文献：
  名称：

  Synthesis and Structure Activity Relationships of 5-Substituted - 4′-thio-β-D-Arabinofuranosylcytosines

  摘要：

  Four 5-substituted (chloro, fluoro, bromo, methyl) 1-(4-thio-beta -D-arabinofuranosyl)cytosines and their a anomers were synthesized by a facile route in high yields. All of these nucleosides were evaluated for cytotoxicity against a panel of human tumor cell lines in vitro. Only 5-fluoro-1-(4-thio-beta -D-arabinofuranosyl)cytosine was found to be highly cytotoxic in all the cell lines and was further evaluated in vivo.

  DOI：

  10.1080/15257770008045474

文献信息

• Synthesis and Structure Activity Relationships of 5-Substituted - 4′-thio-β-D-Arabinofuranosylcytosines
  作者：Kamal N. Tiwari、Anita T. Shortnacy-fowler、Loredana Cappellacci、William R. Waud、William B. Parker、John A. Montgomery、John A. Secrist

  DOI：10.1080/15257770008045474

  日期：2000.10

  Four 5-substituted (chloro, fluoro, bromo, methyl) 1-(4-thio-beta -D-arabinofuranosyl)cytosines and their a anomers were synthesized by a facile route in high yields. All of these nucleosides were evaluated for cytotoxicity against a panel of human tumor cell lines in vitro. Only 5-fluoro-1-(4-thio-beta -D-arabinofuranosyl)cytosine was found to be highly cytotoxic in all the cell lines and was further evaluated in vivo.