1-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)-5-fluorouracil

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)-5-fluorouracil
• 英文别名: 1-(3,5-dihydro-2H-4,1-benzoxathiepin-3-yl)-5-fluoropyrimidine-2,4-dione
• 化学式: C₁₃H₁₁FN₂O₃S
• 分子量: 294.306
• InChiKey: MPFBWPLTIRDGAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-methoxy-2,3-dihydro-5H-4,1-benzoxathiepin 、 5-氟脲嘧啶 在 三甲基氯硅烷 、 四氯化锡 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 20.0h， 以14%的产率得到1-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)-5-fluorouracil
  参考文献：
  名称：

  6′-Chloro-7- or 9-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)-7H- or 9H-purines and their corresponding sulfones as a new family of cytotoxic drugs

  摘要：

  A series of 1-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)pyrimidine derivatives were synthesized and two of them (8 and 9) showed a modest antiproliferative activity against the MCF-7 breast cancer cell line. We then decided to change the pyrimidine base for the more lipophilic 6'-chloropurine, and the N-9'purine (15) and N-7' purine (17) were obtained. The sulfone N-7'-alkylated-6-chloropurine 18 was the most active derivative. Compound 17 was found to be slightly more active than its regioisomer 15, with an activity similar to that of 5-fluorouracil as a reference drug. Encouraged by these values, we tested these compounds against both the HT-29 human colon cancer cell line and the IEC-6 normal rat intestinal epithelial cell line, and 15 was found to be 12.7-fold more active against HT-29 than versus IEC-6. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.023