5-(Bromomethyl)-6-methyluracil | 60484-35-7

• 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: 5-(Bromomethyl)-6-methyluracil
• 英文别名: 5-bromomethyl-6-methyl-1H-pyrimidine-2,4-dione；6-Methyl-5-brommethyluracil；5-(bromomethyl)-6-methyl-1H-pyrimidine-2,4-dione
• CAS: 60484-35-7
• 化学式: C₆H₇BrN₂O₂
• 分子量: 219.038
• InChiKey: RKMUMUIZLOBUMA-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C (decomp)
• 密度：
  1.622±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(Bromomethyl)-6-methyluracil 以28%的产率得到
  参考文献：
  名称：

  ORZESZKO, GRAZYNA;BITNY-SZLACHTO, STANISLAW, ACTA POL. PHARM., 45,(1988) N, C. 237-240

  摘要：

  DOI：
• 作为产物：
  描述：

  6-甲基尿嘧啶 在 sodium hydroxide 、 氢溴酸 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 32.0h， 生成 5-(Bromomethyl)-6-methyluracil
  参考文献：
  名称：

  Total synthesis of the antibiotic sparsomycin, a modified uracil amino acid monoxodithioacetal

  摘要：

  DOI：

  10.1021/jo00329a027

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.
• ORZESZKO, GRAZYNA;BITNY-SZLACHTO, STANISLAW, ACTA POL. PHARM., 45,(1988) N, C. 237-240
  作者：ORZESZKO, GRAZYNA、BITNY-SZLACHTO, STANISLAW

  DOI：——

  日期：——
• Total synthesis of the antibiotic sparsomycin, a modified uracil amino acid monoxodithioacetal
  作者：Harry C. J. Ottenheijm、Rob M. J. Liskamp、Simon P. J. M. Van Nispen、Hans A. Boots、Marian W. Tijhuis

  DOI：10.1021/jo00329a027

  日期：1981.7