N3'-[3-(3-amino-biphenyl-4-ylmethyl)-3H-imidazol-4-ylmethyl]-6'-chloro-N2,N2-dimethylbiphenyl-2,3'-diamine

• 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: N3'-[3-(3-amino-biphenyl-4-ylmethyl)-3H-imidazol-4-ylmethyl]-6'-chloro-N2,N2-dimethylbiphenyl-2,3'-diamine
• 英文别名: 2-[[5-[[4-Chloro-3-(2-piperidin-1-ylphenyl)anilino]methyl]imidazol-1-yl]methyl]-5-phenylaniline；2-[[5-[[4-chloro-3-(2-piperidin-1-ylphenyl)anilino]methyl]imidazol-1-yl]methyl]-5-phenylaniline
• 化学式: C₃₄H₃₄ClN₅
• 分子量: 548.13
• InChiKey: JUAKXGKVHWCEMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  59.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(2-bromophenyl)piperidine 在 tin(II) chloride dihdyrate 、 barium hydroxide octahydrate 作用下， 以 甲醇 、 乙二醇二甲醚 、 水 、 乙酸乙酯 为溶剂， 反应 6.33h， 生成 N3'-[3-(3-amino-biphenyl-4-ylmethyl)-3H-imidazol-4-ylmethyl]-6'-chloro-N2,N2-dimethylbiphenyl-2,3'-diamine
  参考文献：
  名称：

  Dialkylimidazole inhibitors of Trypanosoma cruzi sterol 14α-demethylase as anti-Chagas disease agents

  摘要：

  New dialkylimidazole based sterol 14 alpha-demethylase inhibitors were prepared and tested as potential anti-Trypanosoma cruzi agents. Previous studies had identified compound 2 as the most potent and selective inhibitor against parasite cultures. In addition, animal studies had demonstrated that compound 2 is highly efficacious in the acute model of the disease. However, compound 2 has a high molecular weight and high hydrophobicity, issues addressed here. Systematic modifications were carried out at four positions on the scaffold and several inhibitors were identified which are highly potent (EC50 <1 nM)against T. cruzi in culture. The halogenated derivatives 36j, 36k, and 36p, display excellent activity against T. cruzi amastigotes, with reduced molecular weight and lipophilicity, and exhibit suitable physicochemical properties for an oral drug candidate. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.015

文献信息

• Dialkylimidazole inhibitors of Trypanosoma cruzi sterol 14α-demethylase as anti-Chagas disease agents
  作者：Praveen Kumar Suryadevara、Kishore Kumar Racherla、Srinivas Olepu、Neil R. Norcross、Hari Babu Tatipaka、Jennifer A. Arif、Joseph D. Planer、Galina I. Lepesheva、Christophe L.M.J. Verlinde、Frederick S. Buckner、Michael H. Gelb

  DOI：10.1016/j.bmcl.2013.08.015

  日期：2013.12

  New dialkylimidazole based sterol 14 alpha-demethylase inhibitors were prepared and tested as potential anti-Trypanosoma cruzi agents. Previous studies had identified compound 2 as the most potent and selective inhibitor against parasite cultures. In addition, animal studies had demonstrated that compound 2 is highly efficacious in the acute model of the disease. However, compound 2 has a high molecular weight and high hydrophobicity, issues addressed here. Systematic modifications were carried out at four positions on the scaffold and several inhibitors were identified which are highly potent (EC50 <1 nM)against T. cruzi in culture. The halogenated derivatives 36j, 36k, and 36p, display excellent activity against T. cruzi amastigotes, with reduced molecular weight and lipophilicity, and exhibit suitable physicochemical properties for an oral drug candidate. (C) 2013 Elsevier Ltd. All rights reserved.