ethyl 2-bromo-3-<(S)-4-<<1-(pyridin-2-yl)pyrrolidin-2-yl>methoxy>phenyl>propanoate | 239136-76-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 2-bromo-3-<(S)-4-<<1-(pyridin-2-yl)pyrrolidin-2-yl>methoxy>phenyl>propanoate
• 英文别名: ethyl 2-bromo-3-[4-[[(2S)-1-pyridin-2-ylpyrrolidin-2-yl]methoxy]phenyl]propanoate
• CAS: 239136-76-6
• 化学式: C₂₁H₂₅BrN₂O₃
• 分子量: 433.345
• InChiKey: GYUZUILGFJOQFZ-KKFHFHRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-bromo-3-<(S)-4-<<1-(pyridin-2-yl)pyrrolidin-2-yl>methoxy>phenyl>propanoate 在 盐酸 、 乙醇 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 17.0h， 生成 5-[[4-[[(2S)-1-pyridin-2-ylpyrrolidin-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  Novel Euglycemic and Hypolipidemic Agents. 4. Pyridyl- and Quinolinyl-Containing Thiazolidinediones

  摘要：

  A series of substituted pyridyl- and quinolinyl-containing 2,4-thiazolidinediones having interesting cyclic amine as a linker have been synthesized. Both unsaturated thiazolidinediones 5 and saturated thiazolidinediones 6 and their various salts were evaluated in db/db mice for euglycemic and hypolipidemic effects and compared with BRL compound 11 and BRL-49653, respectively. Some of the potent compounds were converted to various salts in order to obtain improved activities. Among all the salts evaluated, the maleate salt of unsaturated TZD 5a was found to be a very potent euglycemic and hypolipidemic compound. Some of the more interesting compounds have also been evaluated in ob/ob mice and compared with rosiglitazone (maleate salt of BRL-49653). Oral glucose tolerance tests were performed in both db/db and ob/ob mice. Pharmacokinetic studies of 5a maleate are also reported. Receptor binding studies of PPAR gamma by 5a/5a maleate did not show any significant transactivation of PPAR alpha or PPAR gamma.

  DOI：

  10.1021/jm980622j
• 作为产物：
  描述：

  L-脯氨醇 在 copper(I) oxide 、 盐酸 、 氢溴酸 、 铁粉 、 sodium hydride 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 ethyl 2-bromo-3-<(S)-4-<<1-(pyridin-2-yl)pyrrolidin-2-yl>methoxy>phenyl>propanoate
  参考文献：
  名称：

  Novel Euglycemic and Hypolipidemic Agents. 4. Pyridyl- and Quinolinyl-Containing Thiazolidinediones

  摘要：

  A series of substituted pyridyl- and quinolinyl-containing 2,4-thiazolidinediones having interesting cyclic amine as a linker have been synthesized. Both unsaturated thiazolidinediones 5 and saturated thiazolidinediones 6 and their various salts were evaluated in db/db mice for euglycemic and hypolipidemic effects and compared with BRL compound 11 and BRL-49653, respectively. Some of the potent compounds were converted to various salts in order to obtain improved activities. Among all the salts evaluated, the maleate salt of unsaturated TZD 5a was found to be a very potent euglycemic and hypolipidemic compound. Some of the more interesting compounds have also been evaluated in ob/ob mice and compared with rosiglitazone (maleate salt of BRL-49653). Oral glucose tolerance tests were performed in both db/db and ob/ob mice. Pharmacokinetic studies of 5a maleate are also reported. Receptor binding studies of PPAR gamma by 5a/5a maleate did not show any significant transactivation of PPAR alpha or PPAR gamma.

  DOI：

  10.1021/jm980622j

文献信息

• Novel Euglycemic and Hypolipidemic Agents. 4. Pyridyl- and Quinolinyl-Containing Thiazolidinediones
  作者：B. B. Lohray、Vidya Bhushan、A. Sekar Reddy、P. Bheema Rao、N. Jaipal Reddy、P. Harikishore、N. Haritha、Reeba K. Vikramadityan、Ranjan Chakrabarti、R. Rajagopalan、K. Katneni

  DOI：10.1021/jm980622j

  日期：1999.7.1

  A series of substituted pyridyl- and quinolinyl-containing 2,4-thiazolidinediones having interesting cyclic amine as a linker have been synthesized. Both unsaturated thiazolidinediones 5 and saturated thiazolidinediones 6 and their various salts were evaluated in db/db mice for euglycemic and hypolipidemic effects and compared with BRL compound 11 and BRL-49653, respectively. Some of the potent compounds were converted to various salts in order to obtain improved activities. Among all the salts evaluated, the maleate salt of unsaturated TZD 5a was found to be a very potent euglycemic and hypolipidemic compound. Some of the more interesting compounds have also been evaluated in ob/ob mice and compared with rosiglitazone (maleate salt of BRL-49653). Oral glucose tolerance tests were performed in both db/db and ob/ob mice. Pharmacokinetic studies of 5a maleate are also reported. Receptor binding studies of PPAR gamma by 5a/5a maleate did not show any significant transactivation of PPAR alpha or PPAR gamma.