1-(3-(2-hydroxyethylimino)-2-(4-methoxybenzyl)pyrrolidin-1-yl)-3-mercapto-2-methylpropan-1-one | 1163733-15-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(3-(2-hydroxyethylimino)-2-(4-methoxybenzyl)pyrrolidin-1-yl)-3-mercapto-2-methylpropan-1-one
• 英文别名: 1-[3-(2-Hydroxyethylimino)-2-[(4-methoxyphenyl)methyl]pyrrolidin-1-yl]-2-methyl-3-sulfanylpropan-1-one
• CAS: 1163733-15-0
• 化学式: C₁₈H₂₆N₂O₃S
• 分子量: 350.482
• InChiKey: ROPWLEVZIMKXLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  63.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(3-mercapto-2-methylpropanoyl)-2-(4-methoxybenzyl)pyrrolidin-3-one 、 C.I.酸性橙108 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以77%的产率得到1-(3-(2-hydroxyethylimino)-2-(4-methoxybenzyl)pyrrolidin-1-yl)-3-mercapto-2-methylpropan-1-one
  参考文献：
  名称：

  ACE inhibitors hypothesis generation for selective design, synthesis and biological evaluation of 3-mercapto-2-methyl-propanoyl-pyrrolidine-3-imine derivatives as antihypertensive agents

  摘要：

  A series of new 3-mercapto-2-methyl-propanoyl-pyrrolidine derivatives (V, VIa-e) were designed. A new validated ACE inhibitors pharmacophore model (hypothesis) was generated for the first time in this research from the biologically active (frozen) conformation of Lisinopril-Human ACE complex that was downloaded from PDB, using stepwise technique of CATALYST modules. The molecular modeling compare-fit study of the designed molecules (V, VIa-e), with such ACE inhibitors hypothesis was fulfilled, and several compounds showed significant high simulation fit values. The compounds with high fit values were synthesized and biologically evaluated in vivo as hypotensive agents. It appears that the in vivo hypotensive activity of compounds V, VIa, VIb, and VIe was consistent with their molecular modeling results, and compound VIe showed the highest activity in comparison to Captopril. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.008

文献信息

• ACE inhibitors hypothesis generation for selective design, synthesis and biological evaluation of 3-mercapto-2-methyl-propanoyl-pyrrolidine-3-imine derivatives as antihypertensive agents
  作者：Mohamed A.H. Ismail、M. Nabil Aboul-Enein、Khaled A.M. Abouzid、Dalal A. Abou El Ella、Nasser S.M. Ismail

  DOI：10.1016/j.bmc.2009.03.008

  日期：2009.5

  A series of new 3-mercapto-2-methyl-propanoyl-pyrrolidine derivatives (V, VIa-e) were designed. A new validated ACE inhibitors pharmacophore model (hypothesis) was generated for the first time in this research from the biologically active (frozen) conformation of Lisinopril-Human ACE complex that was downloaded from PDB, using stepwise technique of CATALYST modules. The molecular modeling compare-fit study of the designed molecules (V, VIa-e), with such ACE inhibitors hypothesis was fulfilled, and several compounds showed significant high simulation fit values. The compounds with high fit values were synthesized and biologically evaluated in vivo as hypotensive agents. It appears that the in vivo hypotensive activity of compounds V, VIa, VIb, and VIe was consistent with their molecular modeling results, and compound VIe showed the highest activity in comparison to Captopril. (C) 2009 Elsevier Ltd. All rights reserved.