1-(2'-tetrahydrothienyl)-5-fluorouracil 1',1'-dioxide | 93473-98-4

• 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: 1-(2'-tetrahydrothienyl)-5-fluorouracil 1',1'-dioxide
• 英文别名: 1-(1,1-Dioxothiolan-2-yl)-5-fluoropyrimidine-2,4-dione
• CAS: 93473-98-4
• 化学式: C₈H₉FN₂O₄S
• 分子量: 248.235
• InChiKey: YUPJZHWEUDXVQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  91.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(2'-四氢噻吩基)-5-氟尿嘧啶 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以80%的产率得到1-(2'-tetrahydrothienyl)-5-fluorouracil 1',1'-dioxide
  参考文献：
  名称：

  Synthesis and antitumor activity of a series of ftorafur analogs: the effect of varying electronegativity at the 1'-position

  摘要：

  To test the effect of changes in electronegativity within the alicyclic N-1 substituent 5-fluorouracil analogues on cytotoxic activity, a series of derivatives of ftorafur, 1-(2'-tetrahydrofuranyl)-5-fluorouracil, was synthesized and tested for antitumor activity in the P388 lymphocytic leukemia screen and cytotoxic activity in the L1210 cell culture screen. Two compounds of N-1 substituent with high electronegativity, the 2'-tetrahydrothiophene 1'-oxide and the 2'-tetrahydrothiophene 1',1'-dioxide derivatives, demonstrated the highest in vitro L1210 cell inhibition (84.5% and 92.0%, respectively). Furthermore, against P388 lymphocytic leukemia in vivo, the 2'-tetrahydrothiophene 1'-oxide derivative showed significant activity (T/C = 143). Other compounds of similar or lower electronegativity within the N-1 cyclic substituent were inactive against P388 lymphocytic leukemia and less active against L1210 cells.

  DOI：

  10.1021/jm00380a016

文献信息

• XORI, KANE;EHDA, SEEHJ;YASUMOTO, SANDZI;TADA, YUKIO
  作者：XORI, KANE、EHDA, SEEHJ、YASUMOTO, SANDZI、TADA, YUKIO

  DOI：——

  日期：——
• Synthesis and antitumor activity of a series of ftorafur analogs: the effect of varying electronegativity at the 1'-position
  作者：Mark H. Holshouser、Annette M. Shipp、Paul W. Ferguson

  DOI：10.1021/jm00380a016

  日期：1985.2

  To test the effect of changes in electronegativity within the alicyclic N-1 substituent 5-fluorouracil analogues on cytotoxic activity, a series of derivatives of ftorafur, 1-(2'-tetrahydrofuranyl)-5-fluorouracil, was synthesized and tested for antitumor activity in the P388 lymphocytic leukemia screen and cytotoxic activity in the L1210 cell culture screen. Two compounds of N-1 substituent with high electronegativity, the 2'-tetrahydrothiophene 1'-oxide and the 2'-tetrahydrothiophene 1',1'-dioxide derivatives, demonstrated the highest in vitro L1210 cell inhibition (84.5% and 92.0%, respectively). Furthermore, against P388 lymphocytic leukemia in vivo, the 2'-tetrahydrothiophene 1'-oxide derivative showed significant activity (T/C = 143). Other compounds of similar or lower electronegativity within the N-1 cyclic substituent were inactive against P388 lymphocytic leukemia and less active against L1210 cells.