2-[4-[(2-Butyl-1,4-dioxo-2,3-diazaspiro[4.4]nonan-3-yl)methyl]phenyl]benzenesulfonamide | 291774-19-1

• 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-[4-[(2-Butyl-1,4-dioxo-2,3-diazaspiro[4.4]nonan-3-yl)methyl]phenyl]benzenesulfonamide
• CAS: 291774-19-1
• 化学式: C₂₄H₂₉N₃O₄S
• 分子量: 455.578
• InChiKey: ZNQSQYUMNWAPFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  环己基异氰酸酯 、 2-[4-[(2-Butyl-1,4-dioxo-2,3-diazaspiro[4.4]nonan-3-yl)methyl]phenyl]benzenesulfonamide 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以63%的产率得到1-[2-[4-[(2-Butyl-1,4-dioxo-2,3-diazaspiro[4.4]nonan-3-yl)methyl]phenyl]phenyl]sulfonyl-3-cyclohexylurea
  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：

  N-tert-butyl-2-[4-[(2-butyl-1,4-dioxo-2,3-diazaspiro[4.4]nonan-3-yl)methyl]phenyl]benzenesulfonamide 在 苯甲醚 、 三氟乙酸 作用下， 反应 12.0h， 以83%的产率得到2-[4-[(2-Butyl-1,4-dioxo-2,3-diazaspiro[4.4]nonan-3-yl)methyl]phenyl]benzenesulfonamide
  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