6-(dibromomethyl)-2,4-dimethoxy-5-nitropyrimidine | 84538-42-1

• 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: 6-(dibromomethyl)-2,4-dimethoxy-5-nitropyrimidine
• 英文别名: 4-dibromomethyl-2,6-dimethoxy-5-nitropyrimidine；4-(Dibromomethyl)-2,6-dimethoxy-5-nitropyrimidine
• CAS: 84538-42-1
• 化学式: C₇H₇Br₂N₃O₄
• 分子量: 356.958
• InChiKey: WVGCTZXHPQQYAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  6-(dibromomethyl)-2,4-dimethoxy-5-nitropyrimidine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 (2-Methoxy-6-morpholin-4-yl-5-nitropyrimidin-4-yl)methanol
  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：

  2,4-二氯-5-硝基-6-甲基嘧啶 在 溴 、 sodium acetate 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 2.17h， 生成 6-(dibromomethyl)-2,4-dimethoxy-5-nitropyrimidine
  参考文献：
  名称：

  Synthetic strategies for 2,4-dimethoxypyrrolo[3,2-d]pyrimidine

  摘要：

  DOI：

  10.1021/jo00155a026

文献信息

• A novel method for the synthesis of 6,7-unsubstituted pyrrolo[3,2-]pyrimidines
  作者：Thomas L. Cupps、Dean S. Wise、Leroy B. Townsend

  DOI：10.1016/s0040-4039(00)85706-8

  日期：1982.1

  The synthesis of 2,4-dimethoxypyrrolo[3,2-d]pyrimidine (4) is described. This facile, 3-step synthesis involves the bromination of 2,4-dimethoxy-6-methyl-5-nitropyrimidine (1), and the subsequent conversion of compound 1 into compound 4.

  描述了2，4-二甲氧基吡咯并[3，2-d]嘧啶（4）的合成。这种简便的3步合成涉及2,4-二甲氧基-6-甲基-5-硝基嘧啶（1）的溴化反应，然后将化合物1转化为化合物4。
• CUPPS, T. L.;WISE, D. S.;TOWNSEND, L. B., TETRAHEDRON LETT., 1982, 23, N 46, 4759-4762
  作者：CUPPS, T. L.、WISE, D. S.、TOWNSEND, L. B.

  DOI：——

  日期：——
• CUPPS, T. L.;WISE, D. S.;TOWNSEND, L. B., J. ORG. CHEM., 1983, 48, N 7, 1060-1064
  作者：CUPPS, T. L.、WISE, D. S.、TOWNSEND, L. B.

  DOI：——

  日期：——
• Synthetic strategies for 2,4-dimethoxypyrrolo[3,2-d]pyrimidine
  作者：Thomas L. Cupps、Dean S. Wise、Leroy B. Townsend

  DOI：10.1021/jo00155a026

  日期：1983.4
• 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.