1-[3-(4-chlorophenyl)propyl]imidazole | 192943-29-6

• 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-[3-(4-chlorophenyl)propyl]imidazole
• CAS: 192943-29-6
• 化学式: C₁₂H₁₃ClN₂
• 分子量: 220.702
• InChiKey: CLJJKXWBLJQDDT-UHFFFAOYSA-N

物化性质

• 沸点：
  388.6±25.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-[3-(4-chlorophenyl)propyl]imidazole 在 盐酸羟胺 、 sodium acetate 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 2.5h， 生成 ethyl (2Z)-{1-[3-(4-chlorophenyl)propyl]-1H-imidazol-2-yl}(hydroxyimino)acetate
  参考文献：
  名称：

  [EN] NOVEL IMIDAZOLE DERIVATIVES
  [FR] NOUVEAUX DÉRIVÉS D'IMIDAZOLE

  摘要：

  提供了由以下一般式[1]表示的新化合物或其药用盐，其抑制LpxC，以及包含这些化合物或其药用盐的药物，对革兰氏阴性细菌包括多药耐药菌株表现出抗微生物活性，并且在治疗细菌感染中有用。

  公开号：

  WO2018216822A1
• 作为产物：
  描述：

  对氯肉桂酸 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 氢气 、 三溴化磷 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 1-[3-(4-chlorophenyl)propyl]imidazole
  参考文献：
  名称：

  Synthesis, biochemical evaluation and rationalisation of the inhibitory activity of a range of 4-substituted phenyl alkyl imidazole-based inhibitors of the enzyme complex 17α-hydroxylase/17,20-lyase (P45017α)

  摘要：

  We report the preliminary results of the synthesis, biochemical evaluation and rationalisation of the inhibitory activity of a number of phenyl alkyl imidazole-based compounds as inhibitors of the two components of 17 alpha-hydroxylase/17,20-lyase (P450(17 alpha)), that is, 17 alpha-hydroxylase (17 alpha-OHase) and 17,20-lyase (lyase). The results show that N-3-(4-bromophenyl) propyl imidazole (12) (IC50 = 2.95 mu M against 17 alpha-OHase and IC50 = 0.33 mu M against lyase) is the most potent compound within the current study, in comparison to ketoconazole (KTZ) (IC50 = 3.76 mu M against 17 alpha-OHase and IC50 = 1.66 mu M against lyase). Modelling of these compounds suggests that the length of the alkyl chain enhances the interaction between the inhibitor and the area of the active site corresponding to the C(3) area of the steroid backbone, thereby increasing potency. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.092

文献信息

• [EN] NOVEL IMIDAZOLE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS D'IMIDAZOLE
  申请人：TAISHO PHARMA CO LTD

  公开号：WO2018216822A1

  公开（公告）日：2018-11-29

  Provided are novel compounds represented by the following general formula [1] or pharmaceutically acceptable salts thereof, that inhibit LpxC, as well as pharmaceutical drugs comprising those compounds or pharmaceutically acceptable salts thereof, that exhibit antimicrobial activity against gram-negative bacteria including multi-drug resistant strains and that are useful in the treatment of bacterial infections.

  提供了由以下一般式[1]表示的新化合物或其药用盐，其抑制LpxC，以及包含这些化合物或其药用盐的药物，对革兰氏阴性细菌包括多药耐药菌株表现出抗微生物活性，并且在治疗细菌感染中有用。
• Synthesis, biochemical evaluation and rationalisation of the inhibitory activity of a range of 4-substituted phenyl alkyl imidazole-based inhibitors of the enzyme complex 17α-hydroxylase/17,20-lyase (P45017α)
  作者：Chirag H. Patel、Sachin Dhanani、Caroline P. Owen、Sabbir Ahmed

  DOI：10.1016/j.bmcl.2006.06.092

  日期：2006.9

  We report the preliminary results of the synthesis, biochemical evaluation and rationalisation of the inhibitory activity of a number of phenyl alkyl imidazole-based compounds as inhibitors of the two components of 17 alpha-hydroxylase/17,20-lyase (P450(17 alpha)), that is, 17 alpha-hydroxylase (17 alpha-OHase) and 17,20-lyase (lyase). The results show that N-3-(4-bromophenyl) propyl imidazole (12) (IC50 = 2.95 mu M against 17 alpha-OHase and IC50 = 0.33 mu M against lyase) is the most potent compound within the current study, in comparison to ketoconazole (KTZ) (IC50 = 3.76 mu M against 17 alpha-OHase and IC50 = 1.66 mu M against lyase). Modelling of these compounds suggests that the length of the alkyl chain enhances the interaction between the inhibitor and the area of the active site corresponding to the C(3) area of the steroid backbone, thereby increasing potency. (c) 2006 Elsevier Ltd. All rights reserved.