(RS)-6-amino-5-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-carbonylamino)-3-ethoxycarbonylmethyl-1-phenyluracil | 658061-33-7

• 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: (RS)-6-amino-5-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-carbonylamino)-3-ethoxycarbonylmethyl-1-phenyluracil
• CAS: 658061-33-7
• 化学式: C₃₅H₃₈N₄O₇
• 分子量: 626.709
• InChiKey: DSEORMQTTUNQGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  46.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  143.88
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (RS)-6-amino-5-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-carbonylamino)-3-ethoxycarbonylmethyl-1-phenyluracil 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 12.0h， 生成 {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：

  6-amino-3-ethoxycarbonylmethyl-1-phenyluracil 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 8.0h， 生成 (RS)-6-amino-5-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-carbonylamino)-3-ethoxycarbonylmethyl-1-phenyluracil
  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