5-(3-methoxyphenoxy)-1H-pyrimidin-4,6-dione | 202288-10-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(3-methoxyphenoxy)-1H-pyrimidin-4,6-dione
• 英文别名: 5-(3-methoxyphenoxy)-1H-pyrimidine-4,6-dione
• CAS: 202288-10-6
• 化学式: C₁₁H₁₀N₂O₄
• 分子量: 234.211
• InChiKey: TYTLXDABSNFQFA-UHFFFAOYSA-N

物化性质

• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3-methoxyphenoxy)-1H-pyrimidin-4,6-dione 在 吡啶 、 2,3,5-三甲基吡啶 、 盐酸羟胺 、 sodium hydride 、 pyridinium chlorochromate 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 13.5h， 生成 4-tert-butyl-N-[6-(4-hydroxyiminobutoxy)-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of potent and orally active sulfonamide ETB selective antagonists

  摘要：

  The synthesis and structure-activity relationships of a series of N-pyrimidinyl benzenesulfonamides as ETB selective antagonists are described. N-Isoxazolyl benzenesulfonamide 1a. previously reported,(1) was selected as a lead compound, and isosteric replacement of the isoxazole ring of la with a pyrimidine ring led to the discovery of the highly potent ETB selective antagonist 6e with oral bioavailability. Modification of the terminal aldehyde group at the 6-position of the pyrimidine ring was investigated, and malonate 15b and acylhydrazone 16f were found to be equipotent to aldehyde 6e. Compound 6e showed ETB antagonistic activity on in vivo evaluation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00305-9
• 作为产物：
  描述：

  3-甲氧基苯酚 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 22.5h， 生成 5-(3-methoxyphenoxy)-1H-pyrimidin-4,6-dione
  参考文献：
  名称：

  Synthesis and structure–activity relationships of potent and orally active sulfonamide ETB selective antagonists

  摘要：

  The synthesis and structure-activity relationships of a series of N-pyrimidinyl benzenesulfonamides as ETB selective antagonists are described. N-Isoxazolyl benzenesulfonamide 1a. previously reported,(1) was selected as a lead compound, and isosteric replacement of the isoxazole ring of la with a pyrimidine ring led to the discovery of the highly potent ETB selective antagonist 6e with oral bioavailability. Modification of the terminal aldehyde group at the 6-position of the pyrimidine ring was investigated, and malonate 15b and acylhydrazone 16f were found to be equipotent to aldehyde 6e. Compound 6e showed ETB antagonistic activity on in vivo evaluation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00305-9