{4-Amino-5-[(6-benzyloxy-2,5,7,8-tetramethyl-chroman-2-carbonyl)-amino]-2,6-dioxo-3-phenyl-3,6-dihydro-2H-pyrimidin-1-yl}-acetic acid | 856017-97-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: {4-Amino-5-[(6-benzyloxy-2,5,7,8-tetramethyl-chroman-2-carbonyl)-amino]-2,6-dioxo-3-phenyl-3,6-dihydro-2H-pyrimidin-1-yl}-acetic acid
• 英文别名: 2-[4-Amino-2,6-dioxo-3-phenyl-5-[(2,5,7,8-tetramethyl-6-phenylmethoxy-3,4-dihydrochromene-2-carbonyl)amino]pyrimidin-1-yl]acetic acid
• CAS: 856017-97-5
• 化学式: C₃₃H₃₄N₄O₇
• 分子量: 598.656
• InChiKey: HLOYWHXYVKDMHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  152
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  {4-Amino-5-[(6-benzyloxy-2,5,7,8-tetramethyl-chroman-2-carbonyl)-amino]-2,6-dioxo-3-phenyl-3,6-dihydro-2H-pyrimidin-1-yl}-acetic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以209 mg的产率得到{4-Amino-5-[(6-hydroxy-2,5,7,8-tetramethyl-chroman-2-carbonyl)-amino]-2,6-dioxo-3-phenyl-3,6-dihydro-2H-pyrimidin-1-yl}-acetic acid
  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：

  (RS)-6-amino-5-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-carbonylamino)-3-ethoxycarbonylmethyl-1-phenyluracil 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 {4-Amino-5-[(6-benzyloxy-2,5,7,8-tetramethyl-chroman-2-carbonyl)-amino]-2,6-dioxo-3-phenyl-3,6-dihydro-2H-pyrimidin-1-yl}-acetic acid
  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