(E)-5-(2-iodovinyl)-2,4-dichloropyrimidine | 137500-20-0

• 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: (E)-5-(2-iodovinyl)-2,4-dichloropyrimidine
• 英文别名: 2,4-dichloro-5-[(E)-2-iodoethenyl]pyrimidine
• CAS: 137500-20-0
• 化学式: C₆H₃Cl₂IN₂
• 分子量: 300.914
• InChiKey: XZTISISYPDXTJF-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-5-(2-iodovinyl)-2,4-dichloropyrimidine 在 甲醇 、 potassium iodate 、 sodium hydroxide 、 硫酸 、 水 、 碘 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 57.5h， 生成 2,4-二甲氧基5-嘧啶-甲醛
  参考文献：
  名称：

  Synthesis and cytotoxic activity of 5-(1-hydroxy-2-haloethyl)-, 5-oxiranyl- and (E)-5-(2-iodovinyl)-2,4-dichloro (or dimethoxy) pyrimidines

  摘要：

  A series of 5-(1-hydroxy-2-haloethyl) 6, 7, 13, 14a, 5-oxiranyl 8, 9 and (E)-5-(2-iodovinyl)-2,4-dichloro(or dimethoxy)pyrimidines 11, 12 were synthesized for evaluation as cytotoxic agents. The nuclear C-2 and C-4 substituents were determinants of activity since the 2,4-dichloro compounds 6, 8 and 11 were more potent (ED50 = 0.2-0.3-mu-g/ml) than the corresponding 2,4-dimethoxypyrimidine analogues 7, 9 and 12 (ED50 = 4-28-mu-g/ml), relative to melphalan (ED50 = 0.15-mu-g/ml), in the in vitro L1210 screen. Within the 2,4-dichloro series of compounds 6, 8 and 11, the C-5 substituent was not a determinant of activity. In contrast, in the 2,4-dimethoxypyrimidine series, the C-5 substituents influenced activity significantly where the relative potency order was oxiranyl 9 > -CH(OH)CH2I 7 > (E)-CH = CHI 12 > CH(OH)CHI2 13, CH(OH)CHBr(I) 14a and CH(Br)CHOH(I) 14b. The most active compound (E)-5-(2-iodovinyl)-2,4-dichloropyrimidine 11 exhibited weak activity in the in vivo P388 screen (% T/C = 116 for a 10 mg/kg ip dose) relative to the reference drug 5-fluorouracil (% T/C = 135 for a 20 mg/kg dose).

  DOI：

  10.1016/0223-5234(91)90153-e
• 作为产物：
  描述：

  (E)-5-(2-iodovinyl)uracil 在 N,N-二乙基苯胺 、 三氯氧磷 作用下， 反应 0.5h， 以46%的产率得到(E)-5-(2-iodovinyl)-2,4-dichloropyrimidine
  参考文献：
  名称：

  Synthesis and cytotoxic activity of 5-(1-hydroxy-2-haloethyl)-, 5-oxiranyl- and (E)-5-(2-iodovinyl)-2,4-dichloro (or dimethoxy) pyrimidines

  摘要：

  A series of 5-(1-hydroxy-2-haloethyl) 6, 7, 13, 14a, 5-oxiranyl 8, 9 and (E)-5-(2-iodovinyl)-2,4-dichloro(or dimethoxy)pyrimidines 11, 12 were synthesized for evaluation as cytotoxic agents. The nuclear C-2 and C-4 substituents were determinants of activity since the 2,4-dichloro compounds 6, 8 and 11 were more potent (ED50 = 0.2-0.3-mu-g/ml) than the corresponding 2,4-dimethoxypyrimidine analogues 7, 9 and 12 (ED50 = 4-28-mu-g/ml), relative to melphalan (ED50 = 0.15-mu-g/ml), in the in vitro L1210 screen. Within the 2,4-dichloro series of compounds 6, 8 and 11, the C-5 substituent was not a determinant of activity. In contrast, in the 2,4-dimethoxypyrimidine series, the C-5 substituents influenced activity significantly where the relative potency order was oxiranyl 9 > -CH(OH)CH2I 7 > (E)-CH = CHI 12 > CH(OH)CHI2 13, CH(OH)CHBr(I) 14a and CH(Br)CHOH(I) 14b. The most active compound (E)-5-(2-iodovinyl)-2,4-dichloropyrimidine 11 exhibited weak activity in the in vivo P388 screen (% T/C = 116 for a 10 mg/kg ip dose) relative to the reference drug 5-fluorouracil (% T/C = 135 for a 20 mg/kg dose).

  DOI：

  10.1016/0223-5234(91)90153-e