4-{6-acetamido-2-[(3,5-dimethyl-4-methoxypyridin-2-yl)sulfinyl]-1H-benzimidazol-5-yl}piperazine-1-carboxylic acid ethyl ester | 1319671-37-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-{6-acetamido-2-[(3,5-dimethyl-4-methoxypyridin-2-yl)sulfinyl]-1H-benzimidazol-5-yl}piperazine-1-carboxylic acid ethyl ester
• 英文别名: ethyl 4-[6-acetamido-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1H-benzimidazol-5-yl]piperazine-1-carboxylate
• CAS: 1319671-37-8
• 化学式: C₂₅H₃₂N₆O₅S
• 分子量: 528.632
• InChiKey: NQQAYYOVDJHJJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 potassium carbonate 、 potassium hydrogencarbonate 、 三乙胺 、 间氯过氧苯甲酸 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 8.25h， 生成 4-{6-acetamido-2-[(3,5-dimethyl-4-methoxypyridin-2-yl)sulfinyl]-1H-benzimidazol-5-yl}piperazine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  A reverse method for diversity introduction of benzimidazole to synthesize H+/K+-ATP enzyme inhibitors

  摘要：

  A series of 2-[(2-pyridylmethyl)sulfinyl]benzimidazole derivatives were synthesized via a solution phase synthetic route using a reversal method of diversity introduction. Using this synthetic strategy, we obtained two key intermediates (4-A and 4-B) simultaneously, which allows us to introduce diversity points onto the benzimidazole part of the final product under reliable reaction conditions to identify potent H+/K+-ATP enzyme inhibitors. Compound 141 (IC50 = 1.6 x 10 (5) M) was comparable with H+/K+-ATP enzyme inhibitor in vitro. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.080

文献信息

• A reverse method for diversity introduction of benzimidazole to synthesize H+/K+-ATP enzyme inhibitors
  作者：Yu Yan、Zijie Liu、Jianjun Zhang、Ruiming Xu、Xiao Hu、Gang Liu

  DOI：10.1016/j.bmcl.2011.05.080

  日期：2011.7

  A series of 2-[(2-pyridylmethyl)sulfinyl]benzimidazole derivatives were synthesized via a solution phase synthetic route using a reversal method of diversity introduction. Using this synthetic strategy, we obtained two key intermediates (4-A and 4-B) simultaneously, which allows us to introduce diversity points onto the benzimidazole part of the final product under reliable reaction conditions to identify potent H+/K+-ATP enzyme inhibitors. Compound 141 (IC50 = 1.6 x 10 (5) M) was comparable with H+/K+-ATP enzyme inhibitor in vitro. (C) 2011 Elsevier Ltd. All rights reserved.