4,5-dihydro-2-<1-(2,6-dimethylphenoxy)-3-hydroxypropyl>-1H-imidazole | 124316-83-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,5-dihydro-2-<1-(2,6-dimethylphenoxy)-3-hydroxypropyl>-1H-imidazole
• 英文别名: 3-(4,5-dihydro-1H-imidazol-2-yl)-3-(2,6-dimethylphenoxy)propan-1-ol
• CAS: 124316-83-2
• 化学式: C₁₄H₂₀N₂O₂
• 分子量: 248.325
• InChiKey: WQKARHFHTDHFET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,6-二甲基苯酚 在 三甲基铝 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.25h， 生成 4,5-dihydro-2-<1-(2,6-dimethylphenoxy)-3-hydroxypropyl>-1H-imidazole
  参考文献：
  名称：

  Potential antisecretory antidiarrheals. 2. .alpha.2-Adrenergic 2-[(aryloxy)alkyl]imidazolines

  摘要：

  Lofexidine, an alpha 2-agonist, has central hypotensive activity and peripheral intestinal antisecretory activity. Analogues were synthesized with increased polarity in an attempt to prevent penetration of the blood-brain barrier. The compounds were evaluated in the cholera toxin treated ligated jejunum of the rat and in the Ussing chamber with a rabbit ileum preparation. Active compounds were determined to be alpha 2-adrenergic agonists by yohimbine reversals of their Ussing chamber activities. The 2,6-dimethyl derivative of lofexidine, 4a, was as active as lofexidine in vivo, but derivatives with 2,6-substituents larger than ethyl were inactive. (Aryloxy)alkyl derivatives which have an imidazoline and a methyl or larger group as part of the alkyl exhibited the best antisecretory activity. Compounds with substituents in the para position of the phenyl ring were generally inactive. 3-Amino-2,6-dimethyl derivative 21 was twice as active as 4a. A 2-methyl substituent is required in the 3-amino series to retain good activity. 2-Methyl derivative 12a had activity comparable to that of 4a, while 6-methyl derivative 12f was inactive. Substituents on the 3-amino group did not affect the activity, but substituting a hydroxyl for the amino group produced an inactive compound. Replacing the phenyl moiety with a 4-indole resulted in retention of activity, but other heterocycles were inactive. Compound 12a was resolved and d isomer 32 was five times more potent than l isomer 33. The more active compounds in the rat cholera toxin assay (RCTA), when evaluated in the dog, exhibited antisecretory activity but also exhibited central nervous system (CNS) effects, sedation and ataxia, at 10 mg/kg, and in spontaneously hypertensive rats at 50 mg/kg. A measure of polarity, log P, was calculated for the (aryloxy)alkyl groups. Regression analysis showed no correlation of antisecretory ED50 to the calculated log P. The active compounds did not show a separation of the central CNS effects from the peripheral antisecretory activity by increasing the polarity.

  DOI：

  10.1021/jm00164a024

文献信息

• [EN] HALOALKYLSUBSTITUTED ARYLOXYALKYLIMIDAZOLINES FOR USE AS PESTICIDES<br/>[FR] ARYLOXYALKYLIMIDAZOLINES HALOALKYLE-SUBSTITUTEES SERVANT DE PESTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2009060174A1

  公开（公告）日：2009-05-14

  The present invention relates to novel imidazoline derivatives and their use as insecticidal, acaricidal, molluscicidal and nematocidal agents. The invention also extends to insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising such imidazoline derivatives, and to methods of using such derivatives and/or compositions to combat and control insect, acarine, mollusc and nematode pests. A compound of formula (I) : and the salts and N-oxides thereof.

  本发明涉及新型咪唑啉衍生物及其作为杀虫、杀螨、杀软体动物和杀线虫剂的用途。该发明还涉及包含这些咪唑啉衍生物的杀虫、杀螨、杀软体动物和杀线虫的组合物，以及使用这些衍生物和/或组合物来打击和控制昆虫、螨虫、软体动物和线虫害的方法。化合物I的式子如下，包括其盐和N-氧化物。
• Chemical compounds
  申请人：Syngenta Participations AG

  公开号：EP1958507A1

  公开（公告）日：2008-08-20

  The present invention relates to imidazoline derivatives and their use as insecticidal, acaricidal, molluscicidal and nematocidal agents. The invention also extends to insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising such imidazoline derivatives, and to methods of using such derivatives and/or compositions to combat and control insect, acarine, mollusc and nematode pests. In particular the present invention relates to imidazolines with alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, heteroaryl or heterocyclyl substituents.

  本发明涉及咪唑啉衍生物及其作为杀虫、杀螨、杀软体动物和杀线虫剂的用途。该发明还涉及包含这些咪唑啉衍生物的杀虫、杀螨、杀软体动物和杀线虫剂组合物，以及使用这些衍生物和/或组合物来对抗和控制昆虫、螨虫、软体动物和线虫害的方法。特别是本发明涉及具有烷基、环烷基、烯基、环烯基、炔基、芳基、杂芳基或杂环基取代基的咪唑啉。
• CHEMICAL COMPOUNDS
  申请人：O'Sullivan Anthony Cornelius

  公开号：US20100120881A1

  公开（公告）日：2010-05-13

  The present invention relates to imidazoline derivatives and their use as insecticidal, acaricidal, molluscicidal and nematocidal agents. The invention also extends to insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising such imidazoline derivatives, and to methods of using such derivatives and/or compositions to combat and control insect, acarine, mollusc and nematode pests. In particular the present invention relates to imidazolines with alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, heteroaryl or heterocyclyl substituents.

  本发明涉及咪唑啉衍生物及其用作杀虫、杀螨、杀软体动物和杀线虫剂的用途。该发明还涉及包含这些咪唑啉衍生物的杀虫、杀螨、杀软体动物和杀线虫剂组合物，以及使用这些衍生物和/或组合物对抗和控制昆虫、螨虫、软体动物和线虫害的方法。特别是，本发明涉及具有烷基、环烷基、烯基、环烯基、炔基、芳基、杂环芳基或杂环基取代基的咪唑啉。
• HALOALKYLSUBSTITUTED ARYLOXYALKYLIMIDAZOLINES FOR USE AS PESTICIDES
  申请人：Luethy Christoph

  公开号：US20110098331A1

  公开（公告）日：2011-04-28

  The present invention relates to novel imidazoline derivatives and their use as insecticidal, acaricidal, mollus and nematocidal agents. The invention also extends to insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising such imidazoline derivatives, and to methods of using such derivatives and/or compositions to combat and control insect, acarine, mollusc and nematode pests. A compound of formula (I): and the salts and N-oxides thereof.

  本发明涉及新型咪唑啉衍生物及其作为杀虫、杀螨、杀软体动物和杀线虫剂的用途。本发明还扩展到包含这些咪唑啉衍生物的杀虫、杀螨、杀软体动物和杀线虫组合物，以及使用这些衍生物和/或组合物来对抗和控制昆虫、螨虫、软体动物和线虫害的方法。其中化合物的式子为（I）及其盐和N-氧化物。
• US8110593B2
  申请人：——

  公开号：US8110593B2

  公开（公告）日：2012-02-07