6-甲基-5-[(苯基甲氧基)甲基]-2,4(1H,3H)-嘧啶二酮 | 362690-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 6-甲基-5-[(苯基甲氧基)甲基]-2,4(1H,3H)-嘧啶二酮
• 中文别名: 5-苄氧基甲基-6-甲基尿嘧啶
• 英文名称: 5-benzyloxymethyl-6-methyluracil
• 英文别名: 6-methyl-5-(phenylmethoxymethyl)-1H-pyrimidine-2,4-dione
• CAS: 362690-43-5
• 化学式: C₁₃H₁₄N₂O₃
• mdl: MFCD01075201
• 分子量: 246.266
• InChiKey: WOHVAVCCVBQDMC-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C(Solv: ethyl ether (60-29-7))
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-甲基-5-[(苯基甲氧基)甲基]-2,4(1H,3H)-嘧啶二酮 在 palladium on activated charcoal 三甲基氯硅烷 、 氢溴酸 、 甲酸铵 、 sodium hydride 、 溶剂黄146 、 1,2-二溴乙烷 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 生成 5-benzyl-6-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of l‐(Alkoxymethyl)‐5‐benzyl‐6‐methyluracil as Potential Nonnucleoside HIV‐1 RT Inhibitors

  摘要：

  1,3-Dibenzyl-6-methyl-5-zincbromomethyluracil 6 was prepared starting from 6-methyluracil 1. The cross-coupling reaction of benzylic zinc reagent 6 with PhI using bis(dibenzylideneacetone) palladium( 0) and (o-furyl)(3)P as catalyst gave 1,3,5-tribenzyl-6-methyluracil 7. The N-1, N-3-dibenzyl group could be removed in dealkylation to give the 5-benzyl-6-methyluracil 8. It was N-1-alkylated with chloromethyl ethyl ether or chloromethyl benzyl ether to obtained the targets 9a and b. All synthesized compounds were tested for their inhibition of HIV-1 reverse transcriptase, and moderate activity were found for target compounds 9a and b and 5.

  DOI：

  10.1080/00397910600772850
• 作为产物：
  描述：

  6-甲基尿嘧啶 在 盐酸 、 barium dihydroxide 作用下， 以 水 为溶剂， 反应 33.0h， 生成 6-甲基-5-[(苯基甲氧基)甲基]-2,4(1H,3H)-嘧啶二酮
  参考文献：
  名称：

  Synthesis of l‐(Alkoxymethyl)‐5‐benzyl‐6‐methyluracil as Potential Nonnucleoside HIV‐1 RT Inhibitors

  摘要：

  1,3-Dibenzyl-6-methyl-5-zincbromomethyluracil 6 was prepared starting from 6-methyluracil 1. The cross-coupling reaction of benzylic zinc reagent 6 with PhI using bis(dibenzylideneacetone) palladium( 0) and (o-furyl)(3)P as catalyst gave 1,3,5-tribenzyl-6-methyluracil 7. The N-1, N-3-dibenzyl group could be removed in dealkylation to give the 5-benzyl-6-methyluracil 8. It was N-1-alkylated with chloromethyl ethyl ether or chloromethyl benzyl ether to obtained the targets 9a and b. All synthesized compounds were tested for their inhibition of HIV-1 reverse transcriptase, and moderate activity were found for target compounds 9a and b and 5.

  DOI：

  10.1080/00397910600772850

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.
• Synthesis of l‐(Alkoxymethyl)‐5‐benzyl‐6‐methyluracil as Potential Nonnucleoside HIV‐1 RT Inhibitors
  作者：Yanli Chen、Ying Guo、Hua Yang、Xiaowei Wang、Junyi Liu

  DOI：10.1080/00397910600772850

  日期：2006.9.1

  1,3-Dibenzyl-6-methyl-5-zincbromomethyluracil 6 was prepared starting from 6-methyluracil 1. The cross-coupling reaction of benzylic zinc reagent 6 with PhI using bis(dibenzylideneacetone) palladium( 0) and (o-furyl)(3)P as catalyst gave 1,3,5-tribenzyl-6-methyluracil 7. The N-1, N-3-dibenzyl group could be removed in dealkylation to give the 5-benzyl-6-methyluracil 8. It was N-1-alkylated with chloromethyl ethyl ether or chloromethyl benzyl ether to obtained the targets 9a and b. All synthesized compounds were tested for their inhibition of HIV-1 reverse transcriptase, and moderate activity were found for target compounds 9a and b and 5.