N,N'-diphenyl-5-hydroxytetrahydropyrimidin-2-one | 917598-49-3

• 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: N,N'-diphenyl-5-hydroxytetrahydropyrimidin-2-one
• 英文别名: 2(1H)-Pyrimidinone, tetrahydro-5-hydroxy-1,3-diphenyl-；5-hydroxy-1,3-diphenyl-1,3-diazinan-2-one
• CAS: 917598-49-3
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: ZMIZYHBMUKTDNX-UHFFFAOYSA-N

物化性质

• 沸点：
  431.6±34.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-diphenyl-5-hydroxytetrahydropyrimidin-2-one 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 N,N-diphenyltetrahydropyrimidin-2-on-5-yl 4-O-(3'-azido-3'-deoxythymidin-5'-yl)-succinate
  参考文献：
  名称：

  New Azt Conjugates as Potent Anti-HIV Agents

  摘要：

  In an attempt to discover anti-HIV agents with much reduced cytotoxicity from the currently available HIV-reverse transcriptase inhibitors, AZT conjugates of cholanic acids, 2-imidazolidone-4- carboxylic acid and its derivatives, and N, N'-disubstituted 5-hydroxy-tetrahydropyrimidin-2-ones have been synthesized and their anti-HIV profiles determined with CEM-SS cell line. The AZT conjugates with 2-imidazolidone-4- carboxylic acid and 2-pyrrolidone-5-carboxylic acid through an ester linkage, and with N,N'-diphenyl-5-hydroxy-tetrahydropyrimidin-2-one through a succinate tether showed significantly higher therapeutic indexes than AZT while they also retained or enhanced AZT's anti-HIV activity. Thus, structural features that favor the desired therapeutic profile of the conjugates appear to include a five-membered ring cyclic urea or lactam, and six-membered ring cyclic urea with N,N'-diphenyl substitution.

  DOI：

  10.1080/15257770500377789
• 作为产物：
  描述：

  双苯基脲 在 sodium tetrahydroborate 、 potassium permanganate 、 sodium hydride 、 过碘酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 16.66h， 生成 N,N'-diphenyl-5-hydroxytetrahydropyrimidin-2-one
  参考文献：
  名称：

  New Azt Conjugates as Potent Anti-HIV Agents

  摘要：

  In an attempt to discover anti-HIV agents with much reduced cytotoxicity from the currently available HIV-reverse transcriptase inhibitors, AZT conjugates of cholanic acids, 2-imidazolidone-4- carboxylic acid and its derivatives, and N, N'-disubstituted 5-hydroxy-tetrahydropyrimidin-2-ones have been synthesized and their anti-HIV profiles determined with CEM-SS cell line. The AZT conjugates with 2-imidazolidone-4- carboxylic acid and 2-pyrrolidone-5-carboxylic acid through an ester linkage, and with N,N'-diphenyl-5-hydroxy-tetrahydropyrimidin-2-one through a succinate tether showed significantly higher therapeutic indexes than AZT while they also retained or enhanced AZT's anti-HIV activity. Thus, structural features that favor the desired therapeutic profile of the conjugates appear to include a five-membered ring cyclic urea or lactam, and six-membered ring cyclic urea with N,N'-diphenyl substitution.

  DOI：

  10.1080/15257770500377789

文献信息

• New Azt Conjugates as Potent Anti-HIV Agents
  作者：Zhengqing You、Henry Joung Lee

  DOI：10.1080/15257770500377789

  日期：2006.1

  In an attempt to discover anti-HIV agents with much reduced cytotoxicity from the currently available HIV-reverse transcriptase inhibitors, AZT conjugates of cholanic acids, 2-imidazolidone-4- carboxylic acid and its derivatives, and N, N'-disubstituted 5-hydroxy-tetrahydropyrimidin-2-ones have been synthesized and their anti-HIV profiles determined with CEM-SS cell line. The AZT conjugates with 2-imidazolidone-4- carboxylic acid and 2-pyrrolidone-5-carboxylic acid through an ester linkage, and with N,N'-diphenyl-5-hydroxy-tetrahydropyrimidin-2-one through a succinate tether showed significantly higher therapeutic indexes than AZT while they also retained or enhanced AZT's anti-HIV activity. Thus, structural features that favor the desired therapeutic profile of the conjugates appear to include a five-membered ring cyclic urea or lactam, and six-membered ring cyclic urea with N,N'-diphenyl substitution.