1-[(3,4-二氯苯基)甲基]咪唑 | 56643-72-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-[(3,4-二氯苯基)甲基]咪唑
• 英文名称: 1-(3,4-dichloro-benzyl)-1H-imidazole
• 英文别名: 1-(3,4-dichlorobenzyl)-1H-imidazole；CTCB012；1-(3,4-dichloro-benzyl)-1H-imidazole；1-[(3,4-dichlorophenyl)methyl]imidazole
• CAS: 56643-72-2
• 化学式: C₁₀H₈Cl₂N₂
• mdl: MFCD06421439
• 分子量: 227.093
• InChiKey: AYZFQKPOALRPNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  咪唑 、 3,4-二氯氯苄 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以47%的产率得到1-[(3,4-二氯苯基)甲基]咪唑
  参考文献：
  名称：

  N-(3,4-Dichlorobenzyl)azoles—Investigations Regarding Synthesis, NMR-Spectroscopy and Affinity Towards Sisma-1 and Sigma-2 Receptors

  摘要：

  一系列带有3,4-二氯苯甲基基团连接在环氮原子上的唑类和氨基唑类化合物通过将母体系统与3,4-二氯苯甲基氯反应合成。基于13C-NMR数据或NOE差异光谱法鉴别出区域异构体产物。通过受体结合测定确定了一些代表物质对sigma-1和sigma-2受体的亲和力。

  DOI：

  10.3797/scipharm.aut-04-16

文献信息

• Synthesis and biochemical evaluation of a range of potent benzyl imidazole-based compounds as potential inhibitors of the enzyme complex 17α-hydroxylase/17,20-lyase (P45017α)
  作者：Caroline P. Owen、Sachin Dhanani、Chirag H. Patel、Imran Shahid、Sabbir Ahmed

  DOI：10.1016/j.bmcl.2006.05.070

  日期：2006.8

  The cytochrome P-450 enzyme, 17alpha-hydroxylase/17,20-lyase (P450(17alpha)), is a potential target in hormone-dependent cancers. Here, we report the synthesis and biochemical evaluation of a range of benzyl imidazole-based compounds which have been targeted against the two components of this enzyme, that is, 17alpha-hydroxylase (17alpha-OHase) and 17,20-lyase (lyase). The results from the biochemical

  细胞色素P-450酶17α-羟化酶/ 17,20-裂合酶（P450（17alpha））是激素依赖性癌症的潜在靶标。在这里，我们报告了一系列针对该酶的两个成分即17α-羟化酶（17α-OHase）和17,20-裂合酶（裂解酶）的基于苄基咪唑的化合物的合成和生化评估。 。生化测试的结果表明，合成的化合物是良好的抑制剂，与N-4-碘苄基咪唑（5）（针对17α-OHase的IC50 = 10.06 microM和针对裂解酶的IC50 = 1.58 microM）相比，与裂解酶相比，其对裂解酶的活性相等。标准化合物，酮康唑（KTZ）（针对17alpha-OHase的IC50 = 3.76 +/- 0.01 microM，针对裂解酶的IC50 = 1.66 +/- 0.15 microM）。此外，所测试的化合物对17α-OHase成分的效力较弱，
• Synthesis and antitubercular screening of imidazole derivatives☆
  作者：Jyoti Pandey、Vinod K. Tiwari、Shyam S. Verma、Vinita Chaturvedi、S. Bhatnagar、S. Sinha、A.N. Gaikwad、Rama P. Tripathi

  DOI：10.1016/j.ejmech.2009.02.013

  日期：2009.8

  A series of imidazole based compounds were synthesized by reacting simple imidazoles with alkyl halides or alkyl halocarboxylate in presence of tetrabutylammonium bromide (TBAB). The compounds bearing carbethoxy group undergo amidation with different amines in the presence of DBU to give respective carboxamides. The synthesized compounds were screened against Mycobacterium tuberculosis where compound 17 exhibited very good in vitro antitubercular activity and may serve as a lead for further optimization. (C) 2009 Elsevier Masson SAS. All rights reserved.
• N-(3,4-Dichlorobenzyl)azoles—Investigations Regarding Synthesis, NMR-Spectroscopy and Affinity Towards Sisma-1 and Sigma-2 Receptors
  作者：Wolfgang Holzer、Bettina Brandstätter、Christine Jäger、Michael Kaun、Thierry Langer、Wayne D. Bowen

  DOI：10.3797/scipharm.aut-04-16

  日期：——

  A series of azoles and aminoazoles with a 3,4-dichlorobenzyl moiety attached to a ring nitrogen atom was synthesized via reaction of the parent systems with 3,4-dichlorobenzyl chloride. Regioisomeric products were discriminated on the basis of 13C-NMR data or by NOE-difference spectroscopy. The affinities of some representatives towards sigma-1 and sigma-2 receptors were determined by receptor binding assays.

  一系列带有3,4-二氯苯甲基基团连接在环氮原子上的唑类和氨基唑类化合物通过将母体系统与3,4-二氯苯甲基氯反应合成。基于13C-NMR数据或NOE差异光谱法鉴别出区域异构体产物。通过受体结合测定确定了一些代表物质对sigma-1和sigma-2受体的亲和力。