N-(2,4-dichlorobenzyl)-1H-imidazol-1-amine | 153147-57-0

• 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: N-(2,4-dichlorobenzyl)-1H-imidazol-1-amine
• 英文别名: N-[(2,4-dichlorophenyl)methyl]imidazol-1-amine
• CAS: 153147-57-0
• 化学式: C₁₀H₉Cl₂N₃
• 分子量: 242.108
• InChiKey: NJIUIWIJRYMPIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氯-5-氯甲基噻吩 、 N-(2,4-dichlorobenzyl)-1H-imidazol-1-amine 在 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 15.0h， 以32%的产率得到N-(5-chlorothiophen-2-ylmethyl)-N-(2,4-dichlorobenzyl)-1H-imidazol-1-amine
  参考文献：
  名称：

  CYP19 (aromatase): Exploring the scaffold flexibility for novel selective inhibitors

  摘要：

  Several derivatives out of a series of antifungal agents exhibited a good inhibitory potency against aromatase as well as a fairly good selectivity toward CYP17, even if lacking H-bond accepting substituents. Their common structural feature is a flexible backbone that did not fit into previously reported CYP19 models. Thus, a ligand-based approach was exploited to develop a novel statistically robust, self-consistent and predictive 3D-QSAR model herein proposed as a helpful tool to design new aromatase inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.046
• 作为产物：
  描述：

  2,4-二氯苯甲醛 在 sodium tetrahydroborate 、 碳酸氢钠 、 hydroxylamine-O-sulfonic acid 作用下， 以 甲醇 、 水 为溶剂， 反应 47.0h， 生成 N-(2,4-dichlorobenzyl)-1H-imidazol-1-amine
  参考文献：
  名称：

  A New Class of Antifungal Agents. Synthesis and Antimycotic Activity of DisubstitutedN-Azolylamines

  摘要：

  In this study we extended our exploration of the N-azolylamine moiety for its antifungal activity. We prepared a number of N-azolylamino derivatives. The synthetic sequence includes the preparation of aminoazole Schiff bases, and the reduction and the alkylation of the corresponding secondary amines. The title compounds were evaluated in vitro against several pathogenic fungi responsible for human disease. The most potent antimicrobial compound was the N-(biphenyl-4-yl)methyl-N-(2,4-dichlorophenyl)methyl-1H-imidazol-1-ylamine (21), which was found to be active against yeasts and dermatophytes; its potency and selectivity were comparable to those of miconazole.

  DOI：

  10.1002/1521-4184(20009)333:9<299::aid-ardp299>3.0.co;2-f

文献信息

• A New Class of Antifungal Agents. Synthesis and Antimycotic Activity of DisubstitutedN-Azolylamines
  作者：Sabrina Castellano、Giorgio Stefancich、Chiara Musiu、Paolo La Colla

  DOI：10.1002/1521-4184(20009)333:9<299::aid-ardp299>3.0.co;2-f

  日期：2000.9

  In this study we extended our exploration of the N-azolylamine moiety for its antifungal activity. We prepared a number of N-azolylamino derivatives. The synthetic sequence includes the preparation of aminoazole Schiff bases, and the reduction and the alkylation of the corresponding secondary amines. The title compounds were evaluated in vitro against several pathogenic fungi responsible for human disease. The most potent antimicrobial compound was the N-(biphenyl-4-yl)methyl-N-(2,4-dichlorophenyl)methyl-1H-imidazol-1-ylamine (21), which was found to be active against yeasts and dermatophytes; its potency and selectivity were comparable to those of miconazole.
• CYP19 (aromatase): Exploring the scaffold flexibility for novel selective inhibitors
  作者：Sabrina Castellano、Giorgio Stefancich、Rino Ragno、Katarzyna Schewe、Marisabella Santoriello、Antonia Caroli、Rolf W. Hartmann、Gianluca Sbardella

  DOI：10.1016/j.bmc.2008.08.046

  日期：2008.9

  Several derivatives out of a series of antifungal agents exhibited a good inhibitory potency against aromatase as well as a fairly good selectivity toward CYP17, even if lacking H-bond accepting substituents. Their common structural feature is a flexible backbone that did not fit into previously reported CYP19 models. Thus, a ligand-based approach was exploited to develop a novel statistically robust, self-consistent and predictive 3D-QSAR model herein proposed as a helpful tool to design new aromatase inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.