5-(1-bromo-2-hydroxy-2-iodoethyl)-2,4-dimethoxypyrimidine | 137500-24-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(1-bromo-2-hydroxy-2-iodoethyl)-2,4-dimethoxypyrimidine
• 英文别名: 2-Bromo-2-(2,4-dimethoxypyrimidin-5-yl)-1-iodoethanol
• CAS: 137500-24-4
• 化学式: C₈H₁₀BrIN₂O₃
• 分子量: 388.987
• InChiKey: BBEHROMEGLNKJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-5-(2-iodovinyl)uracil 在 甲醇 、 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 76.5h， 生成 5-(1-bromo-2-hydroxy-2-iodoethyl)-2,4-dimethoxypyrimidine
  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