2-[[4-(1-adamantyl)phenoxy]methyl]-N-[(3-methylfuran-2-yl)methyl]-3H-benzimidazole-5-carboxamide | 1415560-86-9

• 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: 2-[[4-(1-adamantyl)phenoxy]methyl]-N-[(3-methylfuran-2-yl)methyl]-3H-benzimidazole-5-carboxamide
• CAS: 1415560-86-9
• 化学式: C₃₁H₃₃N₃O₃
• 分子量: 495.621
• InChiKey: MQJHFLHSZQENPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  80.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4-二氨基苯甲酸甲酯 在 盐酸 、 溶剂黄146 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 2-[[4-(1-adamantyl)phenoxy]methyl]-N-[(3-methylfuran-2-yl)methyl]-3H-benzimidazole-5-carboxamide
  参考文献：
  名称：

  Discovery of a novel series of benzimidazole derivatives as diacylglycerol acyltransferase inhibitors

  摘要：

  A novel series of benzimidazole derivatives was prepared and evaluated for their diacylglycerol acyltransferase (DGAT) inhibitory activity using microsome from rat liver. Among the newly synthesized compounds, furfurylamine containing benzimidazole carboxamide 10j showed the most potent DGAT inhibitory effect (IC50 = 4.4 mu M) and inhibited triglyceride formation in HepG2 cells. Furthermore, compound 10j reduced body weight gain of Institute of Cancer Research mice on a high-fat diet and decreased levels of total triglyceride, total cholesterol, and LDL-cholesterol in the blood accompanied with a significant increase in HDL-cholesterol level. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.046

文献信息

• Discovery of a novel series of benzimidazole derivatives as diacylglycerol acyltransferase inhibitors
  作者：Kyeong Lee、Ja-Il Goo、Hwa Young Jung、Minkyoung Kim、Shanthaveerappa K. Boovanahalli、Hye Ran Park、Mun-Ock Kim、Dong-Hyun Kim、Hyun Sun Lee、Yongseok Choi

  DOI：10.1016/j.bmcl.2012.10.046

  日期：2012.12

  A novel series of benzimidazole derivatives was prepared and evaluated for their diacylglycerol acyltransferase (DGAT) inhibitory activity using microsome from rat liver. Among the newly synthesized compounds, furfurylamine containing benzimidazole carboxamide 10j showed the most potent DGAT inhibitory effect (IC50 = 4.4 mu M) and inhibited triglyceride formation in HepG2 cells. Furthermore, compound 10j reduced body weight gain of Institute of Cancer Research mice on a high-fat diet and decreased levels of total triglyceride, total cholesterol, and LDL-cholesterol in the blood accompanied with a significant increase in HDL-cholesterol level. (C) 2012 Elsevier Ltd. All rights reserved.