N-[(4-hydroxy-6-phenyl)pyrimidin-2-yl]-N’-phenylguanidine

• 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-[(4-hydroxy-6-phenyl)pyrimidin-2-yl]-N’-phenylguanidine
• 英文别名: 1-(6-Oxo-4-phenyl-1,6-dihydropyrimidin-2-yl)-3-phenylguanidine；2-(6-oxo-4-phenyl-1H-pyrimidin-2-yl)-1-phenylguanidine
• 化学式: C₁₇H₁₅N₅O
• 分子量: 305.339
• InChiKey: QTRZDRHAVHIINW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.9
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (4-hydroxy-6-phenyl-2-pyrimidynyl)cyanamide 、 苯胺 以 异丙醇 为溶剂， 110.0~120.0 ℃ 、3.5 MPa 条件下， 反应 0.17h， 以81%的产率得到N-[(4-hydroxy-6-phenyl)pyrimidin-2-yl]-N’-phenylguanidine
  参考文献：
  名称：

  N'-芳基/（烷基）取代的N-（4-羟基-6-苯基嘧啶-2-基）胍的有效微波辅助合成：范围和局限性

  摘要：

  在微波条件下，在110-120°C的条件下，在异丙醇中用1°烷基或芳基胺对N-[（4-羟基-6-苯基）嘧啶-2-基]氰酰胺进行处理仅10分钟，得到相应的N'-烷基（芳基）胍衍生物的产率极高（65-84％）。大于1.0当量时，孤立的产量最高。使用芳族胺，但是当芳基胺和烷基胺以更高的原子经济负荷（1.0当量；分别为70％和72％的产率）反应时，也获得了优异的结果。具有高吸电子取代基（例如CO 2）的芳胺H）或缺乏pi的杂环（例如各种取代的氨基吡啶）在这些条件下不能很好地起作用，并且与尿素和/或氨基酸的反应没有得到可检测的产物。处理非常简单，只需在烧结玻璃漏斗中收集和清洗产品即可。获得的产品均为分析纯形式，大约需要1个小时才能制备，开始精加工。

  DOI：

  10.1016/j.tetlet.2017.03.063

文献信息

• Age-Related Increase of Brain Cyclooxygenase Activity and Dietary Modulation of Oxidative Status
  作者：B. S. Baek、J. W. Kim、J. H. Lee、H. J. Kwon、N. D. Kim、H. S. Kang、M. A. Yoo、B. P. Yu、H. Y. Chung

  DOI：10.1093/gerona/56.10.b426

  日期：2001.10.1

  Several studies have demonstrated that inhibitors of cyclooxygenase (COX) attenuate various neuronal injuries and age-dependent demented conditions. From these findings, we proposed to test the effect of age on COX activity and its. possible suppression by the antiaging action of dietary restriction in the rat brain. The status of reactive oxygen species (ROS) was also assessed to correlate with COX activity to delineate the underlying mechanism of the altered COX activity during aging. These results showed that COX activity significantly increased in 24-month-old rats compared with 6-month-old rats in an ad libitum group. Interestingly, mRNA and protein levels of COX-2 showed little corresponding age-related change. The formation of ROS was found to increase gradually with age in ad libitum fed rats. However, dietary restriction suppressed the increase at the age of 24 months. To substantiate the relationship between ROS and COX activity when the rats were 24 months of age, we conducted in vitro experiments with a C6 glioma cell line. Together, it is concluded that increased COX activity with age is due to the activation of COX catalytic reaction by ROS without increased gene expression of COX-2 and that it is related to the increased pro-oxidant status in aged rats.