1-[2-butoxy-2-(2,4-dichloro-phenyl)-ethyl]-1H-imidazole | 47062-22-6

• 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: 1-[2-butoxy-2-(2,4-dichloro-phenyl)-ethyl]-1H-imidazole
• 英文别名: 1-(β-butoxy-2,4-dichlorophenethyl)-imidazole；1-(beta-Butoxy-2,4-dichlorophenethyl)-imidazole；1-[2-butoxy-2-(2,4-dichlorophenyl)ethyl]imidazole
• CAS: 47062-22-6
• 化学式: C₁₅H₁₈Cl₂N₂O
• 分子量: 313.227
• InChiKey: JSXXXWSOGFZVDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[2-butoxy-2-(2,4-dichloro-phenyl)-ethyl]-1H-imidazole 、 (p-chlorophenyl)-(p-fluorophenyl)methyl chloride 以 乙腈 为溶剂， 反应 16.0h， 以to obtain as residue a 1-(β-butoxy2,4-dichlorophenethyl)-3-[p-chloro-a-(p-fluorophenyl)benzyl]imidazolium chloride product的产率得到1-(beta-Butoxy-2,4-dichlorophenethyl)-3-[p-chloro-alpha-(p-fluorophenyl)benzyl]imidazolium chloride
  参考文献：
  名称：

  Imidazolium salts

  摘要：

  一种新型的四元咪唑盐，其中咪唑阳离子中的一个氮原子被取代为一个##EQU1##基团，其中每个A是一个芳基基团，B是一个脂肪烷基、芳基取代脂肪烷基或芳基基团。这些盐可用作抗微生物剂。

  公开号：

  US03991202A1
• 作为产物：
  描述：

  正溴丁烷 、 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26%的产率得到1-[2-butoxy-2-(2,4-dichloro-phenyl)-ethyl]-1H-imidazole
  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，
• US3991202A
  申请人：——

  公开号：US3991202A

  公开（公告）日：1976-11-09
• US4017631A
  申请人：——

  公开号：US4017631A

  公开（公告）日：1977-04-12
• Imidazolium salts
  申请人：Janssen Pharmaceutica N.V.

  公开号：US03991202A1

  公开（公告）日：1976-11-09

  Novel quaternary imidazolium salts substituted on one nitrogen of the imidazolium cation with a ##EQU1## group in which each A is an aryl radical and B is an aliphatic, aryl-substituted aliphatic or aromatic radical, said salts being useful as antimicrobial agents.

  新型的四元咪唑盐，其中咪唑阳离子的一个氮原子上取代有一个##EQU1##基团，其中每个A是芳基基团，B是脂肪基、芳基取代的脂肪基或芳基基团，这些盐可用作抗微生物剂。
• Aliphatic ethers and esters of 1-(2,4-dichlorophenyl)-2-(1H-imidazolyl) ethanol: study of antifungal activity against yeasts and hydrophobic character
  作者：Y Wahbi、C Tournaire、R Caujolle、M Payard、MD Linas、JP Seguela

  DOI：10.1016/0223-5234(94)90032-9

  日期：1994.1

  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.