1-(benzyloxymethyl)-5-(bromomethyl)-6-methyluracil | 957149-05-2

• 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: 1-(benzyloxymethyl)-5-(bromomethyl)-6-methyluracil
• CAS: 957149-05-2
• 化学式: C₁₄H₁₅BrN₂O₃
• 分子量: 339.189
• InChiKey: LMQKKKAACQPHDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.09
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(benzyloxymethyl)-5-(bromomethyl)-6-methyluracil 、 2,4,6-三氯苯胺 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以28%的产率得到6-Methyl-1-(phenylmethoxymethyl)-5-[(2,4,6-trichloroanilino)methyl]pyrimidine-2,4-dione
  参考文献：
  名称：

  The design and synthesis of N-1-alkylated-5-aminoaryalkylsubstituted-6-methyluracils as potential non-nucleoside HIV-1 RT inhibitors

  摘要：

  Novel compounds 1a-u, which can be considered as hybrid analogues of MKC-442 and pyridinon, have been synthesized and evaluated as inhibitors of HIV-1 reverse transcriptase (HIV-1 RT). Starting from 6-methyuracil 2, 1-alkylated-5-bromomethyl-6-methyluracils 8 was prepared in four steps by hydroxylmethylation, etherification, N-1 alkylation, and bromination. Finally, compounds 1a-u were achieved in the displacement of 5-bromomethyl group by nucleophiles with amino compounds. Some of compounds 1a-u showed potent inhibitory activity against HIV-1 RT. The most active compounds showed activity in the low micromolecular range with IC50 values (IC50 0.82-5.09 mu M) comparable to that of nevirapine (IC50 10.60 mu M). The biological testing results are in accordance with the docking. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.058
• 作为产物：
  描述：

  1-(benzyloxymethyl)-5-(benzyloxymethyl)-6-methyluracil 在 氢溴酸 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 以46%的产率得到1-(benzyloxymethyl)-5-(bromomethyl)-6-methyluracil
  参考文献：
  名称：

  The design and synthesis of N-1-alkylated-5-aminoaryalkylsubstituted-6-methyluracils as potential non-nucleoside HIV-1 RT inhibitors

  摘要：

  Novel compounds 1a-u, which can be considered as hybrid analogues of MKC-442 and pyridinon, have been synthesized and evaluated as inhibitors of HIV-1 reverse transcriptase (HIV-1 RT). Starting from 6-methyuracil 2, 1-alkylated-5-bromomethyl-6-methyluracils 8 was prepared in four steps by hydroxylmethylation, etherification, N-1 alkylation, and bromination. Finally, compounds 1a-u were achieved in the displacement of 5-bromomethyl group by nucleophiles with amino compounds. Some of compounds 1a-u showed potent inhibitory activity against HIV-1 RT. The most active compounds showed activity in the low micromolecular range with IC50 values (IC50 0.82-5.09 mu M) comparable to that of nevirapine (IC50 10.60 mu M). The biological testing results are in accordance with the docking. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.058