6-Hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid [6-amino-1-(3-benzyloxy-phenyl)-3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-amide | 566921-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-Hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid [6-amino-1-(3-benzyloxy-phenyl)-3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-amide
• CAS: 566921-82-2
• 化学式: C₃₂H₃₄N₄O₆
• 分子量: 570.645
• InChiKey: GDEOKUBOLNEJOH-UHFFFAOYSA-N

物化性质

• 熔点：
  128-130 °C
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  42.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  137.81
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  6-Hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid [6-amino-1-(3-benzyloxy-phenyl)-3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-amide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以97%的产率得到
  参考文献：
  名称：

  Structure and activity relationships of novel uracil derivatives as topical anti-inflammatory agents

  摘要：

  In order to create novel, topical anti-inflammatory compounds exhibiting more potent activities than lead compound CX-659S (1), we designed and synthesized various derivatives of 1 focusing on the uracil N(l)- and N(3)-substituents, and evaluated their anti-inflammatory activities via inhibition of the picryl chloride-induced contact hypersensitivity reaction (CHR) in mice. In the course of our structure and activity relationship study, we found that compounds 6k, 6q, and 6r inhibited by approximately 50% the CHR, at 0.1 mg/ear. These activities were essentially equipotent with that of Tacrolimus, a strong immunosuppressant. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.012
• 作为产物：
  描述：

  2,4(1H,3H)-Pyrimidinedione,6-amino-3-methyl-1-[3-(phenylmethoxy)phenyl]- 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙胺 、 sodium nitrite 、 二苯基次膦酰氯 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 7.0h， 生成 6-Hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid [6-amino-1-(3-benzyloxy-phenyl)-3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-amide
  参考文献：
  名称：

  Structure and activity relationships of novel uracil derivatives as topical anti-inflammatory agents

  摘要：

  In order to create novel, topical anti-inflammatory compounds exhibiting more potent activities than lead compound CX-659S (1), we designed and synthesized various derivatives of 1 focusing on the uracil N(l)- and N(3)-substituents, and evaluated their anti-inflammatory activities via inhibition of the picryl chloride-induced contact hypersensitivity reaction (CHR) in mice. In the course of our structure and activity relationship study, we found that compounds 6k, 6q, and 6r inhibited by approximately 50% the CHR, at 0.1 mg/ear. These activities were essentially equipotent with that of Tacrolimus, a strong immunosuppressant. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.012