N-[1-(3-hydroxyiminobutyl)-4,5-dihydroimidazol-2-yl]nitramide | 1135467-41-2

• 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: N-[1-(3-hydroxyiminobutyl)-4,5-dihydroimidazol-2-yl]nitramide
• CAS: 1135467-41-2
• 化学式: C₇H₁₃N₅O₃
• 分子量: 215.212
• InChiKey: AVRYDXXIBZZYAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(3-oxobutyl)-2-nitroiminoimidazolidine 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 3.5h， 以62%的产率得到N-[1-(3-hydroxyiminobutyl)-4,5-dihydroimidazol-2-yl]nitramide
  参考文献：
  名称：

  Neonicotinoid Substituents Forming a Water Bridge at the Nicotinic Acetylcholine Receptor

  摘要：

  Neonicotinoid insecticides are extensively used for crop protection. The chloropyridinyl or chlorothiazolyl nitrogen and tetrahydrofuryl oxygen atoms of neonicotinoids serve as hydrogen acceptors at the target site. This investigation designs and prepares neonicotinoid probes to understand the structure-activity relationships (SARs) at the target site focusing on the water-mediated ligand-protein interactions. 2-Nitroiminoimidazolidine analogues with hydrogen-acceptor N-CH2CH2CH2F and N-CH2CH2C(O)CH3 substituents showed higher binding affinities to the Drosophila melanogaster nicotinic receptor than probes with different hydrogen-bonding points in location and capability, suggesting that the appropriately positioned fluorine or carbonyl oxygen plays an important role on hydrogen-bond formation. Their binding site interactions were predicted using a crystal structure of the acetylcholine binding protein. The fluorine or carbonyl oxygen forms a water bridge to Ile-118 (and/or Ile-106) at the binding domain, consistent with that of neonicotinoids with a chloropyridinylmethyl, chlorothiazolylmethyl, or tetrahydrofurylmethyl moiety. Therefore, the present SAR study on binding site interactions helps design potent neonicotinoids with novel substituents.

  DOI：

  10.1021/jf803985r

文献信息

• Neonicotinoid Substituents Forming a Water Bridge at the Nicotinic Acetylcholine Receptor
  作者：Ikuya Ohno、Motohiro Tomizawa、Kathleen A. Durkin、John E. Casida、Shinzo Kagabu

  DOI：10.1021/jf803985r

  日期：2009.3.25

  Neonicotinoid insecticides are extensively used for crop protection. The chloropyridinyl or chlorothiazolyl nitrogen and tetrahydrofuryl oxygen atoms of neonicotinoids serve as hydrogen acceptors at the target site. This investigation designs and prepares neonicotinoid probes to understand the structure-activity relationships (SARs) at the target site focusing on the water-mediated ligand-protein interactions. 2-Nitroiminoimidazolidine analogues with hydrogen-acceptor N-CH2CH2CH2F and N-CH2CH2C(O)CH3 substituents showed higher binding affinities to the Drosophila melanogaster nicotinic receptor than probes with different hydrogen-bonding points in location and capability, suggesting that the appropriately positioned fluorine or carbonyl oxygen plays an important role on hydrogen-bond formation. Their binding site interactions were predicted using a crystal structure of the acetylcholine binding protein. The fluorine or carbonyl oxygen forms a water bridge to Ile-118 (and/or Ile-106) at the binding domain, consistent with that of neonicotinoids with a chloropyridinylmethyl, chlorothiazolylmethyl, or tetrahydrofurylmethyl moiety. Therefore, the present SAR study on binding site interactions helps design potent neonicotinoids with novel substituents.