2,4-diethoxy-6-methyl-5-nitropyrimidine | 172982-62-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2,4-diethoxy-6-methyl-5-nitropyrimidine
• 英文别名: 2,4-diethoxy-6-methyl-5-nitro-pyrimidine；2,4-Diaethoxy-6-methyl-5-nitro-pyrimidin；2,4-Diethoxy-5-nitro-6-methyl-pyrimidin
• CAS: 172982-62-6
• 化学式: C₉H₁₃N₃O₄
• 分子量: 227.22
• InChiKey: HZAXPJJFHFQYMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  90.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-diethoxy-6-methyl-5-nitropyrimidine 在 溴 、 sodium acetate 、 溶剂黄146 作用下， 以70%的产率得到4-(Dibromomethyl)-2,6-diethoxy-5-nitropyrimidine
  参考文献：
  名称：

  Synthesis and Evaluation of 6-(Dibromomethyl)-5-nitropyrimidines as Potential Antitumor Agents

  摘要：

  A series of 2,4,6-trisubstituted-5-nitropyrimidines have been prepared and evaluated for inhibition of proliferation of L1210 and H.Ep.2 cells in vitro. The most potent compound was 6-(dibromomethyl)-2-methoxy-4-morpholino-5-nitropyrimidine (11) (L1210, IC50 0.32 mu M; H.Ep.2, IC50 = 1.6 mu M). Of the 6-substituents incorporated, only CHBr2, CH2Br, and CHO were compatible with antiproliferative activity, while a wider variety of 4-substituents were tolerated. At concentrations near the IC50 for antiproliferative activity, a delayed resumption of cell proliferation in L1210 cultures indicated that the activity of the compounds was short-lived and suggested they might act by an alkylation mechanism.

  DOI：

  10.1021/jm9605546
• 作为产物：
  描述：

  2,4-二乙氧基-6-甲基嘧啶 在 硫酸 、 硝酸 作用下， 生成 2,4-diethoxy-6-methyl-5-nitropyrimidine
  参考文献：
  名称：

  Some Pyrimidine Derivatives¹

  摘要：

  DOI：

  10.1021/ja01118a525

文献信息

• Tanaka et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1955, vol. 75, p. 770
  作者：Tanaka et al.

  DOI：——

  日期：——
• Some Pyrimidine Derivatives¹
  作者：Joseph L. Rabinowitz、Samuel Gurin

  DOI：10.1021/ja01118a525

  日期：1953.11
• Synthesis and Evaluation of 6-(Dibromomethyl)-5-nitropyrimidines as Potential Antitumor Agents
  作者：M. Daniel Thompson、Thomas L. Cupps、Dean S. Wise、Linda L. Wotring、Leroy B. Townsend

  DOI：10.1021/jm9605546

  日期：1997.2.1

  A series of 2,4,6-trisubstituted-5-nitropyrimidines have been prepared and evaluated for inhibition of proliferation of L1210 and H.Ep.2 cells in vitro. The most potent compound was 6-(dibromomethyl)-2-methoxy-4-morpholino-5-nitropyrimidine (11) (L1210, IC50 0.32 mu M; H.Ep.2, IC50 = 1.6 mu M). Of the 6-substituents incorporated, only CHBr2, CH2Br, and CHO were compatible with antiproliferative activity, while a wider variety of 4-substituents were tolerated. At concentrations near the IC50 for antiproliferative activity, a delayed resumption of cell proliferation in L1210 cultures indicated that the activity of the compounds was short-lived and suggested they might act by an alkylation mechanism.