5-oxiranyl-2,4-dimethoxypyrimidine | 137500-19-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-oxiranyl-2,4-dimethoxypyrimidine
• 英文别名: 2,4-Dimethoxy-5-(oxiran-2-yl)pyrimidine；2,4-dimethoxy-5-(oxiran-2-yl)pyrimidine
• CAS: 137500-19-7
• 化学式: C₈H₁₀N₂O₃
• 分子量: 182.179
• InChiKey: VXWXZFGXWYFOQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-乙烯尿嘧啶 在 甲醇 、 potassium iodate 、 calcium hydroxide 、 硫酸 、 碘 、 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 氯仿 、 水 、 乙腈 为溶剂， 反应 56.5h， 生成 5-oxiranyl-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

文献信息

• Synthesis and cytotoxic activity of 5-(1-hydroxy-2-haloethyl)-, 5-oxiranyl- and (E)-5-(2-iodovinyl)-2,4-dichloro (or dimethoxy) pyrimidines
  作者：R Kumar、EE Knaus、LI Wiebe、TM Allen、ML Tempest

  DOI：10.1016/0223-5234(91)90153-e

  日期：1991.7

  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).