1-butyl-4,4-dimethylpyrazolidine-3,5-dione | 291773-99-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 1-butyl-4,4-dimethylpyrazolidine-3,5-dione
• CAS: 291773-99-4
• 化学式: C₉H₁₆N₂O₂
• 分子量: 184.238
• InChiKey: OYCNRSZUKJDUDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-butyl-4,4-dimethylpyrazolidine-3,5-dione 在 吡啶 、 potassium carbonate 、 苯甲醚 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 80.0h， 生成 N-[2-[4-[(2-butyl-4,4-dimethyl-3,5-dioxopyrazolidin-1-yl)methyl]phenyl]phenyl]sulfonylbenzamide
  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：

  二甲基丙二酸二乙酯 在 sodium ethanolate 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 1-butyl-4,4-dimethylpyrazolidine-3,5-dione
  参考文献：
  名称：

  N-烷基吡唑烷-3,5-二酮和四氢哒嗪-3,6-二酮的新合成

  摘要：

  N-烷基吡唑烷-3，5-二酮和四氢哒嗪-3，6-二酮通过新方法以三步顺序分别由丙二酸二烷基酯或琥珀酸酯合成。

  DOI：

  10.1002/jhet.5570370530

文献信息

• Synthesis and Pharmacological Evaluation of New Pyrazolidine-3,5-diones as AT₁ Angiotensin II Receptor Antagonists
  作者：Bertrand Le Bourdonnec、Emmanuelle Meulon、Saïd Yous、Jean-François Goossens、Raymond Houssin、Jean-Pierre Hénichart

  DOI：10.1021/jm9904147

  日期：2000.7.1

  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.
• A new synthesis of<i>N</i>-alkyl pyrazolidine-3,5-diones and tetrahydropyridazine-3,6-diones
  作者：Bertrand Le Bourdonnec、Emmanuelle Meulon、Saïd Yous、Raymond Houssin、Jean-Pierre Hénichart

  DOI：10.1002/jhet.5570370530

  日期：2000.9

  N-alkyl pyrazolidine-3,5-diones and tetrahydropyridazine-3,6-diones have been synthesized by a new method in a three-step sequence from dialkyl malonates or succinates respectively.

  N-烷基吡唑烷-3，5-二酮和四氢哒嗪-3，6-二酮通过新方法以三步顺序分别由丙二酸二烷基酯或琥珀酸酯合成。