cyclohexylmethyl (S)-4-(3-((tert-butyldimethylsilyl)oxy)phenyl)-6-ethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 1224680-16-3

• 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: cyclohexylmethyl (S)-4-(3-((tert-butyldimethylsilyl)oxy)phenyl)-6-ethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• CAS: 1224680-16-3
• 化学式: C₂₆H₄₀N₂O₄Si
• 分子量: 472.7
• InChiKey: CEKLIEPFIOJWTJ-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  76.66
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  cyclohexylmethyl (S)-4-(3-((tert-butyldimethylsilyl)oxy)phenyl)-6-ethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.17h， 以17 mg的产率得到cyclohexylmethyl 6-ethyl-4-(3-hydroxyphenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Discovery of 3,4-dihydropyrimidin-2(1H)-ones with inhibitory activity against HIV-1 replication

  摘要：

  3,4-Dihydropyrimidin-2(1H)-ones (DHPMs) were selected and derivatized through a HIV-1 replication assay based on GFP reporter cells. Compounds 14, 25, 31, and 36 exhibited significant inhibition of HIV-1 replication with a good safety profile. Chiral separation of each enantiomer by fractional crystallization showed that only the S enantiomer retained anti-HIV activity. Compound (S)-40, a novel and potent DHPM analog, could serve as an advanced lead for further development and the determination of the mechanism of action. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.090
• 作为产物：
  描述：

  benzyl 6-ethyl-4-(3-hydroxyphenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， -20.0~76.0 ℃ 、300.01 kPa 条件下， 反应 3.0h， 生成 cyclohexylmethyl (S)-4-(3-((tert-butyldimethylsilyl)oxy)phenyl)-6-ethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Discovery of 3,4-dihydropyrimidin-2(1H)-ones with inhibitory activity against HIV-1 replication

  摘要：

  3,4-Dihydropyrimidin-2(1H)-ones (DHPMs) were selected and derivatized through a HIV-1 replication assay based on GFP reporter cells. Compounds 14, 25, 31, and 36 exhibited significant inhibition of HIV-1 replication with a good safety profile. Chiral separation of each enantiomer by fractional crystallization showed that only the S enantiomer retained anti-HIV activity. Compound (S)-40, a novel and potent DHPM analog, could serve as an advanced lead for further development and the determination of the mechanism of action. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.090