5-氯-N-[2-(4-氯苯基)乙基]-2-甲氧基苯甲酰胺 | 87262-54-2

• 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: 5-氯-N-[2-(4-氯苯基)乙基]-2-甲氧基苯甲酰胺
• 英文名称: Benzamide, 5-chloro-N-[2-(4-chlorophenyl)ethyl]-2-methoxy-
• 英文别名: 5-chloro-N-[2-(4-chlorophenyl)ethyl]-2-methoxybenzamide
• CAS: 87262-54-2
• 化学式: C₁₆H₁₅Cl₂NO₂
• 分子量: 324.207
• InChiKey: PGKRZFXOEXBTSY-UHFFFAOYSA-N

物化性质

• 沸点：
  463.8±45.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯苯乙胺 、 5-氯-2-甲氧基苯甲酰氯 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以70%的产率得到5-氯-N-[2-(4-氯苯基)乙基]-2-甲氧基苯甲酰胺
  参考文献：
  名称：

  Receptor binding sites of hypoglycemic sulfonylureas and related [(acylamino)alkyl]benzoic acids

  摘要：

  The blood glucose level lowering activity of [(acylamino)ethyl]benzoic acids, such as p-[2-(5-chloro-2-methoxy-benzamido)ethyl]benzoic acid (HB699, 2), is discussed in terms of binding at putative insulin-releasing receptor sites of pancreatic beta cells. The hypoglycemic potencies found for synthetic analogues of 2 indicate that high hypoglycemic activity is only found when a carboxyl group or a group that is readily oxidized to carboxyl in vivo, such as methyl, is attached to the aromatic ring of the phenethyl group. It is proposed that this carboxyl group is able to bind at the same receptor site as the SO2NHCONH group of the sulfonylurea drugs, such as tolbutamide (3). The role of the benzamide group in 2 was attributed to protein binding.

  DOI：

  10.1021/jm00367a016

文献信息

• Receptor binding sites of hypoglycemic sulfonylureas and related [(acylamino)alkyl]benzoic acids
  作者：George R. Brown、Alan J. Foubister

  DOI：10.1021/jm00367a016

  日期：1984.1

  The blood glucose level lowering activity of [(acylamino)ethyl]benzoic acids, such as p-[2-(5-chloro-2-methoxy-benzamido)ethyl]benzoic acid (HB699, 2), is discussed in terms of binding at putative insulin-releasing receptor sites of pancreatic beta cells. The hypoglycemic potencies found for synthetic analogues of 2 indicate that high hypoglycemic activity is only found when a carboxyl group or a group that is readily oxidized to carboxyl in vivo, such as methyl, is attached to the aromatic ring of the phenethyl group. It is proposed that this carboxyl group is able to bind at the same receptor site as the SO2NHCONH group of the sulfonylurea drugs, such as tolbutamide (3). The role of the benzamide group in 2 was attributed to protein binding.