2-butyl-3-(4-carbomethoxybenzyl)-2,3-diazaspiro[4.4]nonane-1,4-dione | 291774-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-butyl-3-(4-carbomethoxybenzyl)-2,3-diazaspiro[4.4]nonane-1,4-dione
• 英文别名: Methyl 4-[(2-butyl-1,4-dioxo-2,3-diazaspiro[4.4]nonan-3-yl)methyl]benzoate
• CAS: 291774-34-0
• 化学式: C₂₀H₂₆N₂O₄
• 分子量: 358.437
• InChiKey: QYMSEWCYWXQWMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-butyl-3-(4-carbomethoxybenzyl)-2,3-diazaspiro[4.4]nonane-1,4-dione 在 盐酸 、 sodium hydroxide 、 氯化亚砜 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 2-{4-[(3-butyl-1,4-dioxo-2,3-diazaspiro[4.4]non-2-yl)methyl]benzamido}benzoic acid
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of New Pyrazolidine-3,5-diones as AT₁ Angiotensin II Receptor Antagonists

  摘要：

  On the basis of the structure of the non-peptide receptor antagonist irbesartan, a new series of AT(1) ligands was designed. In these compounds the central imidazolone nucleus of irbesartan was replaced by a pyrazolidine-3,5-dione structure. The key intermediate N-alkylpyrazolidine3,5-dioneswere synthesized according to a new and general method. The most active compounds possess a spirocyclopentane ring at position 4, a linear butyl chain at position 1, and the [2'-(5-tetrazolyl)biphenyl-4-yl]methyl or [2'-(benzoylaminosulfonyl)biphenyl-4-yl] group at position 2. Affinity toward the AT(1) and AT(2) receptors was assessed by the ability of the compounds to competitively displace [H-3]AII from its specific binding sites. The most active compounds, 28 and 48, displayed high affinity for the AT(1) receptor, good selectivity AT(1) versus AT(2), and potent in vitro antagonist activity.

  DOI：

  10.1021/jm9904147
• 作为产物：
  描述：

  2-benzyl-2,3-diazaspiro[4.4]nonane-1,4-dione 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 19.0h， 生成 2-butyl-3-(4-carbomethoxybenzyl)-2,3-diazaspiro[4.4]nonane-1,4-dione
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of New Pyrazolidine-3,5-diones as AT₁ Angiotensin II Receptor Antagonists

  摘要：

  On the basis of the structure of the non-peptide receptor antagonist irbesartan, a new series of AT(1) ligands was designed. In these compounds the central imidazolone nucleus of irbesartan was replaced by a pyrazolidine-3,5-dione structure. The key intermediate N-alkylpyrazolidine3,5-dioneswere synthesized according to a new and general method. The most active compounds possess a spirocyclopentane ring at position 4, a linear butyl chain at position 1, and the [2'-(5-tetrazolyl)biphenyl-4-yl]methyl or [2'-(benzoylaminosulfonyl)biphenyl-4-yl] group at position 2. Affinity toward the AT(1) and AT(2) receptors was assessed by the ability of the compounds to competitively displace [H-3]AII from its specific binding sites. The most active compounds, 28 and 48, displayed high affinity for the AT(1) receptor, good selectivity AT(1) versus AT(2), and potent in vitro antagonist activity.

  DOI：

  10.1021/jm9904147