1-(2'-四氢噻吩基)-5-氟尿嘧啶 | 68321-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 1-(2'-四氢噻吩基)-5-氟尿嘧啶
• 英文名称: 1-(2'-tetrahydrothienyl)-5-fluorouracil
• 英文别名: 5-fluoro-1-tetrahydrothiophen-2-yl-1H-pyrimidine-2,4-dione；2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-thienyl)-；5-fluoro-1-(thiolan-2-yl)pyrimidine-2,4-dione
• CAS: 68321-44-8
• 化学式: C₈H₉FN₂O₂S
• 分子量: 216.236
• InChiKey: PLCFCSKGIXYEOZ-UHFFFAOYSA-N

物化性质

• 熔点：
  180-181 °C(Solv: ethyl acetate (141-78-6))
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 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：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-(acetoxy)tetrahydrothiophene 、 O,O’-双(三甲基硅烷)-5-氟尿嘧啶 在 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 1-(2'-四氢噻吩基)-5-氟尿嘧啶
  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

• KRUSE C. G.; POELS E. K.; GEN A., J. ORG. CHEM., 1979, 44, NO 16, 2911-2915
  作者：KRUSE C. G.、 POELS E. K.、 GEN A.

  DOI：——

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

  DOI：——

  日期：——
• JPS56167685A
  申请人：——

  公开号：JPS56167685A

  公开（公告）日：1981-12-23
• 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.