6-Methyl-1-(phenylmethoxymethyl)-5-[(2,4,6-trichloroanilino)methyl]pyrimidine-2,4-dione | 957149-01-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-Methyl-1-(phenylmethoxymethyl)-5-[(2,4,6-trichloroanilino)methyl]pyrimidine-2,4-dione
• CAS: 957149-01-8
• 化学式: C₂₀H₁₈Cl₃N₃O₃
• 分子量: 454.74
• InChiKey: AOYYXDNXFXZQIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  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

文献信息

• The design and synthesis of N-1-alkylated-5-aminoaryalkylsubstituted-6-methyluracils as potential non-nucleoside HIV-1 RT inhibitors
  作者：Xiao Lu、Yanli Chen、Ying Guo、Zhenming Liu、Yawei Shi、Yang Xu、Xiaowei Wang、Zhili Zhang、Junyi Liu

  DOI：10.1016/j.bmc.2007.07.058

  日期：2007.12

  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.