5-hydroxy-2-(4-hydroxyphenyl)-1-[4-(2-piperidin-1-ylethoxy)benzyl]-1H-benzimidazole | 1240736-72-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-hydroxy-2-(4-hydroxyphenyl)-1-[4-(2-piperidin-1-ylethoxy)benzyl]-1H-benzimidazole
• 英文别名: 5-Hydroxy-2-(4-hydroxyphenyl)-1-[4-(2-piperidin-1-ylethoxy)benzyl]-1H-benzimidazole；2-(4-hydroxyphenyl)-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]benzimidazol-5-ol
• CAS: 1240736-72-4
• 化学式: C₂₇H₂₉N₃O₃
• 分子量: 443.546
• InChiKey: IJADTDWJQKPPBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  70.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(2-piperidin-1-ylethoxy)benzyl bromide hydrobromide 、 ethyl 4-methoxybenzimidate hydrochloride 、 4-甲氧基邻苯二胺 在 aluminum (III) chloride 、 乙硫醇 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 4.5h， 以45%的产率得到5-hydroxy-2-(4-hydroxyphenyl)-1-[4-(2-piperidin-1-ylethoxy)benzyl]-1H-benzimidazole
  参考文献：
  名称：

  2-Phenyl-1-[4-(2-piperidine-1-yl-ethoxy)benzyl]-1H-benzimidazoles as ligands for the estrogen receptor: Synthesis and pharmacological evaluation

  摘要：

  2-Phenyl-1H-benzimidazoles 7a-e were synthesized and tested for gene activation on ERa-positive MCF-7 breast cancer cells, stably transfected with the reporter plasmid ERE(wtc)luc (MCF-7-2a cells). None of the compounds showed agonistic properties, but they antagonized dependent on hydroxyl groups at the benzimidazole core (5- or 6-OH) and at the aromatic ring in the 2-position (4-OH) in high concentrations the gene activation induced by estradiol (E2, 1 nM). All compounds exhibited significant antiproliferative properties on MCF-7 cells but they were inactive against hormone independent, ER negative MDA-MB-231 cells. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.016

文献信息

• 2-Phenyl-1-[4-(2-piperidine-1-yl-ethoxy)benzyl]-1H-benzimidazoles as ligands for the estrogen receptor: Synthesis and pharmacological evaluation
  作者：Sandra Dettmann、Katrin Szymanowitz、Anja Wellner、Anke Schiedel、Christa E. Müller、Ronald Gust

  DOI：10.1016/j.bmc.2010.06.016

  日期：2010.7

  2-Phenyl-1H-benzimidazoles 7a-e were synthesized and tested for gene activation on ERa-positive MCF-7 breast cancer cells, stably transfected with the reporter plasmid ERE(wtc)luc (MCF-7-2a cells). None of the compounds showed agonistic properties, but they antagonized dependent on hydroxyl groups at the benzimidazole core (5- or 6-OH) and at the aromatic ring in the 2-position (4-OH) in high concentrations the gene activation induced by estradiol (E2, 1 nM). All compounds exhibited significant antiproliferative properties on MCF-7 cells but they were inactive against hormone independent, ER negative MDA-MB-231 cells. (C) 2010 Elsevier Ltd. All rights reserved.