1H-Imidazole, 1-[2-(2,4-dichlorophenyl)-2-(nonyloxy)ethyl]- | 159647-09-3

• 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: 1H-Imidazole, 1-[2-(2,4-dichlorophenyl)-2-(nonyloxy)ethyl]-
• 英文别名: 1-[2-(2,4-dichlorophenyl)-2-nonoxyethyl]imidazole
• CAS: 159647-09-3
• 化学式: C₂₀H₂₈Cl₂N₂O
• 分子量: 383.361
• InChiKey: QSKUTZJYCQKGFF-UHFFFAOYSA-N

物化性质

• 沸点：
  507.7±50.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-溴壬烷 、 alpha-(2,4-二氯苯基)-1H-咪唑-1-乙醇 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以40%的产率得到1H-Imidazole, 1-[2-(2,4-dichlorophenyl)-2-(nonyloxy)ethyl]-
  参考文献：
  名称：

  Aliphatic ethers and esters of 1-(2,4-dichlorophenyl)-2-(1H-imidazolyl) ethanol: study of antifungal activity against yeasts and hydrophobic character

  摘要：

  Aliphatic ethers 2 and esters 3, which are closely related to antifungal azoles, were synthesized and tested against various strains of Candida. We found that their activity was strongly related to the length of the chains; the best activity was obtained with a C-6 chain for ethers and C-5 or C-6 chains for esters (including the carbonyl group), whereas shorter or longer alkyl chains decreased antifungal efficiency. The biological activity of such compounds could be related to their ability to bind with the lipophilic area near the active site of enzymatic target. The lipophilic character increases with the length of chain, following a linear variation. Thus, even if the activity depends on the lipophilic influence, this particular property is not sufficient to totally explain the antifungal efficiency.

  DOI：

  10.1016/0223-5234(94)90032-9

文献信息

• Design and synthesis of novel imidazole derivatives as potent inhibitors of allene oxide synthase(CYP74)
  作者：Keimei Oh、Noboru Murofushi

  DOI：10.1016/s0968-0896(02)00422-4

  日期：2002.12

  series of novel imidazole derivatives and tested them in a bioassay as AOS inhibitors using a purified recombinant AOS enzyme isolated from Arabidopsis and expressed in E. coli. Among the derivatives prepared, heptyl 8-[1-(2,4-dichlorophenyl)-2-imidazolylethoxy]octanoate (k) was found to be the most potent inhibitor, with an IC(50) of 10+/-5 nM, which is 250,000-fold and 1,000,000-fold more potent than

  丙二烯氧化合酶（AOS）是植物中脂蛋白途径中的关键酶，可导致茉莉酸和其他茉莉酸（JAs），这是植物防御信号网络的重要信号介体。AOS使用氢过氧亚麻酸作为氧供体以及底物，因此13（S）-氢过氧亚麻酸向氧杂环丁烷的生化转化可以在没有氧气和NADPH的情况下进行。我们设计了一系列新型咪唑衍生物的合成物，并使用从拟南芥中分离并在大肠杆菌中表达的纯化重组AOS酶在生物测定中作为AOS抑制剂进行了测试。在制备的衍生物中，发现八-[1-（2,4-二氯苯基）-2-咪唑并甲氧基]辛酸庚酯（k）是最有效的抑制剂，IC（50）为10 +/- 5 nM，是250,000倍和1,000，