4-(3,4-二甲氧基苯基)-2-氧代-3-吡咯烷羧酸乙酯 | 54280-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 4-(3,4-二甲氧基苯基)-2-氧代-3-吡咯烷羧酸乙酯
• 英文名称: ethyl 4-(3,4-dimethoxyphenyl)-2-oxo-3-pyrrolidinecarboxylate
• 英文别名: 3-Ethoxycarbonyl-4-(3,4-dimethoxyphenyl)-2-pyrrolidinon；ethyl 4-(3,4-dimethoxyphenyl)-2-oxopyrrolidine-3-carboxylate
• CAS: 54280-36-3
• 化学式: C₁₅H₁₉NO₅
• 分子量: 293.32
• InChiKey: PQCRPXRLLDACRS-UHFFFAOYSA-N

物化性质

• 熔点：
  108 °C(Solv: ethanol (64-17-5))
• 沸点：
  468.2±45.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3,4-二甲氧基苯基)-2-氧代-3-吡咯烷羧酸乙酯 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 4-(3,4-dimethoxy-phenyl)-2-oxo-pyrrolidine-3-carboxylic acid
  参考文献：
  名称：

  Inhibition of cyclic adenosine-3',5'-monophosphate phosphodiesterase from vascular smooth muscle by rolipram analogs

  摘要：

  Rolipram [(R,S)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidone] has been shown to inhibit selectively the cAMP phosphodiesterase (PDE) of vascular smooth muscle. In order to further explore the structural requirements for selective PDE inhibition, we synthesized a series of rolipram derivatives differently substituted either at the pyrrolidinone or at the aromatic ring. Among these compounds, rolipram was the most active compound. Semirigid analogues were prepared and used for an evaluation of the active conformation of rolipram. Structural comparison with two other potent and chemically different smooth muscle cAMP-PDE inhibitors, trequinsin and Ro 20-1724, allows us to propose a first topological model of the smooth muscle cAMP-PDE pharmacophore.

  DOI：

  10.1021/jm00127a009

文献信息

• Substituted pyrrolidinemethanols
  申请人：Yoshitomi Pharmaceutical Industries, Ltd.

  公开号：US03935217A1

  公开（公告）日：1976-01-27

  Substituted pyrrolidinemethanols of the formula: ##SPC1## Wherein R.sup.1 and R.sup.2 are each H or C.sub.1.sub.-4 alkyl; R.sup.3, R.sup.4 and R.sup.5 are each H, halogen, C.sub.1.sub.-4 alkyl or C.sub.1.sub.-4 alkoxy, or R.sup.3 and R.sup.4 combinedly form methylenedioxy; and R is C.sub.1.sub.-10 alkyl or a group of the formula: ##SPC2## Where R.sup.6, R.sup.7 and R.sup.8 are each H, halogen, C.sub.1.sub.-4 alkyl or C.sub.1.sub.-4 alkoxy, or R.sup.6 and R.sup.7 combinedly form methylenedioxy; and pharmaceutically acceptable acid addition salts thereof are disclosed. They are useful as drugs for the treatment of diseases of the heart and circulation.

  公式为：##SPC1## 其中 R.sup.1 和 R.sup.2 分别为 H 或 C.sub.1.sub.-4 烷基；R.sup.3、R.sup.4 和 R.sup.5 分别为 H、卤素、C.sub.1.sub.-4 烷基或 C.sub.1.sub.-4 烷氧基，或者 R.sup.3 和 R.sup.4 共同形成亚甲二氧基；R 为 C.sub.1.sub.-10 烷基或公式：##SPC2## 其中 R.sup.6、R.sup.7 和 R.sup.8 分别为 H、卤素、C.sub.1.sub.-4 烷基或 C.sub.1.sub.-4 烷氧基，或者 R.sup.6 和 R.sup.7 共同形成亚甲二氧基；以及其药学上可接受的酸盐。它们可用作治疗心脏和循环疾病的药物。
• YUKI, XIROSI;YATABEH, MASAXIRO
  作者：YUKI, XIROSI、YATABEH, MASAXIRO

  DOI：——

  日期：——
• US3935217A
  申请人：——

  公开号：US3935217A

  公开（公告）日：1976-01-27
• Inhibition of cyclic adenosine-3',5'-monophosphate phosphodiesterase from vascular smooth muscle by rolipram analogs
  作者：Michel C. Marivet、Jean Jacques Bourguignon、Claire Lugnier、Andre Mann、Jean Claude Stoclet、Camille Georges Wermuth

  DOI：10.1021/jm00127a009

  日期：1989.7

  Rolipram [(R,S)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidone] has been shown to inhibit selectively the cAMP phosphodiesterase (PDE) of vascular smooth muscle. In order to further explore the structural requirements for selective PDE inhibition, we synthesized a series of rolipram derivatives differently substituted either at the pyrrolidinone or at the aromatic ring. Among these compounds, rolipram was the most active compound. Semirigid analogues were prepared and used for an evaluation of the active conformation of rolipram. Structural comparison with two other potent and chemically different smooth muscle cAMP-PDE inhibitors, trequinsin and Ro 20-1724, allows us to propose a first topological model of the smooth muscle cAMP-PDE pharmacophore.