(R)-1-[5-(4'-chlorobiphenyl-4-yloxy)-3-methylpentyl]-3-pyridin-4-ylimidazolidin-2-one

• 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: (R)-1-[5-(4'-chlorobiphenyl-4-yloxy)-3-methylpentyl]-3-pyridin-4-ylimidazolidin-2-one
• 英文别名: 1-[(3R)-5-[4-(4-chlorophenyl)phenoxy]-3-methyl-pentyl]-3-(4-pyridyl)imidazolidin-2-one；1-[(3R)-5-[4-(4-chlorophenyl)phenoxy]-3-methylpentyl]-3-pyridin-4-ylimidazolidin-2-one
• 化学式: C₂₆H₂₈ClN₃O₂
• 分子量: 449.98
• InChiKey: MKZAASYEYXYPHA-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  45.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 3-(R)-methyl-5-hydroxypentanoate 在 吡啶 、 硼烷四氢呋喃络合物 、 sodium hydride 、 potassium carbonate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.0h， 生成 (R)-1-[5-(4'-chlorobiphenyl-4-yloxy)-3-methylpentyl]-3-pyridin-4-ylimidazolidin-2-one
  参考文献：
  名称：

  Synthesis and antipicornavirus activity of (R)- and (S)-1-[5-(4′-chlorobiphenyl-4-yloxy)-3-methylpentyl]-3-pyridin-4-yl-imidazolidin-2-one

  摘要：

  The new pyridyl imidazolidinone derivative, 1-[5-(4'-chlorobiphenyl-4-yloxy)-3-methylpentyl]-3-pyridin-4-yl-imidazolidin-2-one (+/-)-1a, was synthesized and found to have an excellent antiviral activity against EV71 (IC50 = 0.009 mu M). Therefore, both the enantiomers, (S)-(+)-1a and (R)-(-)-1a, have been prepared starting from readily available monomethyl (R)-3-methylglutarate (7) as a useful chiral building block and their antiviral activity was evaluated in a plaque reduction assay. Interestingly, we observed that the enantiomer (S)-(+)-1a was 10-fold more active against enterovirus71 (EV71) (IC50 = 0.003 mu M) than the corresponding enantiomer (R)-(-)-1a (IC50 = 0.033 mu M). Similar results were found against all five strains (1743, 2086, 2231, 4643, and BrCr) of EV71 tested. This demonstrated that the absolute configuration of the chiral carbon atom at the 3-position of the alkyl linker considerably influenced the anti-EV71 activity of these pyridyl imidazolidinones. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.069

文献信息

• Imidazolidinone compounds
  申请人：——

  公开号：US20040116476A1

  公开（公告）日：2004-06-17

  This invention relates to compounds of the following formula: 1 in which R 1 , R 2 , A 1 , A 2 , X, Y, m, n, p, x and y are as defined herein, pharmaceutical compositions comprising the compounds and use of the compounds in treating enterovirus infection.

  本发明涉及以下式子的化合物：1其中R1，R2，A1，A2，X，Y，m，n，p，x和y如此定义，以及包含这些化合物的药物组成物和使用这些化合物治疗肠道病毒感染。
• US7129359B2
  申请人：——

  公开号：US7129359B2

  公开（公告）日：2006-10-31
• US7501445B2
  申请人：——

  公开号：US7501445B2

  公开（公告）日：2009-03-10