methyl 6-(1H-benzo[d]imidazol-2-yl)hexanoate

• 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: methyl 6-(1H-benzo[d]imidazol-2-yl)hexanoate
• 英文别名: methyl 6-(1H-benzimidazol-2-yl)hexanoate
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: XFFOCNOHZJSKBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 6-(1H-benzo[d]imidazol-2-yl)hexanoate 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 6-(1H-benzo[d]imidazol-2-yl)-N-hydroxyhexanamide
  参考文献：
  名称：

  Identification of novel HDAC inhibitors through cell based screening and their evaluation as potential anticancer agents

  摘要：

  A series of benzimidazole based HDAC inhibitors have been rationally designed, synthesized and screened. The SAR of this new chemotype is described. The lead compound, 11e, showed strong activity in several cellular assays and demonstrated in vivo efficacy in mouse xenograft pancreatic cancer models. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.001
• 作为产物：
  描述：

  5-溴-2-硝基苯胺 在 dihydroxyborane 、 四(三苯基膦)钯 、 palladium on activated charcoal 、 甲酸铵 、 potassium carbonate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 methyl 6-(1H-benzo[d]imidazol-2-yl)hexanoate
  参考文献：
  名称：

  Identification of novel HDAC inhibitors through cell based screening and their evaluation as potential anticancer agents

  摘要：

  A series of benzimidazole based HDAC inhibitors have been rationally designed, synthesized and screened. The SAR of this new chemotype is described. The lead compound, 11e, showed strong activity in several cellular assays and demonstrated in vivo efficacy in mouse xenograft pancreatic cancer models. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.001

文献信息

• Reaction of 1,3-dicarbonyl compounds with<i>o</i>-phenylenediamine or 3,3′-diaminobenzidine in water or under solvent-free conditions via microwave irradiation
  作者：Zhong-Xia Wang、Hua-Li Qin

  DOI：10.1002/jhet.5570420540

  日期：2005.7

  Reaction of ophenylenediamine with β-diketones or β-ketoesters in water formed 2-substituted benzimi-dazoles. Reaction of 3,3′-diaminobenzidine gave similar results. Under microwave irradiation conditions solvent-free reaction of o-phenylenediamine with β-ketoesters afforded l,5-benzodiazepin-2-one derivatives. An exception is the reaction of o-phenylenediamine with ethyl acetoacetate under microwave

  邻苯二胺与β-二酮或β-酮酸酯在水中的反应形成2-取代的苯并咪唑。3，3′-二氨基联苯胺的反应得到相似的结果。在微波辐射条件下，邻苯二胺与β-酮酸酯的无溶剂反应得到1，5-苯并二氮杂-2-酮衍生物。例外是邻苯二胺与乙酰乙酸乙酯在微波辐射下反应，得到2-甲基苯并咪唑。