4-[4-(1-benzyloxy-(R)-ethyl)-6-chloro-[1,3,5]triazin-2-yl]piperazine-1-sulfonic acid dimethylamide | 654071-76-8

• 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-[4-(1-benzyloxy-(R)-ethyl)-6-chloro-[1,3,5]triazin-2-yl]piperazine-1-sulfonic acid dimethylamide
• CAS: 654071-76-8
• 化学式: C₁₈H₂₅ClN₆O₃S
• 分子量: 440.954
• InChiKey: SRSDQPMJSPJJHR-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.73
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  91.76
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-[4-(1-benzyloxy-(R)-ethyl)-6-chloro-[1,3,5]triazin-2-yl]piperazine-1-sulfonic acid dimethylamide 在 palladium on activated charcoal 盐酸 、 ammonium formate 作用下， 以 乙醚 、 异丙醇 为溶剂， 反应 2.0h， 生成 4-[4-((R)-1-Hydroxy-ethyl)-[1,3,5]triazin-2-yl]-piperazine-1-sulfonic acid dimethylamide
  参考文献：
  名称：

  Design and synthesis of a novel family of triazine-based inhibitors of sorbitol dehydrogenase with oral activity: 1-?4-[3R,5S-dimethyl-4-(4-methyl-[1,3,5]triazin-2-yl)-piperazin-1-yl]-[1,3,5]triazin-2-yl?-(R) ethanol

  摘要：

  Two new templates, (R) 2-hydroxyethyl-pyridine and (R) 2-hydroxyethyl-triazine, were used to design novel sorbitol dehydrogenase inhibitors (SDIs). The design concept included spawning of these templates to function as effective ligands to the catalytic zinc within the enzyme through incorporation of optimally substituted piperazino-triazine side chains so as to accommodate the active site in the enzyme for efficient binding. This strategy resulted in orally active SDIs, which penetrate key tissues, for example, sciatic nerve of chronically diabetic rats. The latter template led to the design of the title inhibitor, 33, which normalized the elevated sciatic nerve fructose by 96% at an oral dose of 10 mg/kg. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00490-5
• 作为产物：
  描述：

  6-(1-benzyloxy-(R)-ethyl)-1H-[1,3,5]triazine-2,4-dione 在 碳酸氢钠 、 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4-[4-(1-benzyloxy-(R)-ethyl)-6-chloro-[1,3,5]triazin-2-yl]piperazine-1-sulfonic acid dimethylamide
  参考文献：
  名称：

  Design and synthesis of a novel family of triazine-based inhibitors of sorbitol dehydrogenase with oral activity: 1-?4-[3R,5S-dimethyl-4-(4-methyl-[1,3,5]triazin-2-yl)-piperazin-1-yl]-[1,3,5]triazin-2-yl?-(R) ethanol

  摘要：

  Two new templates, (R) 2-hydroxyethyl-pyridine and (R) 2-hydroxyethyl-triazine, were used to design novel sorbitol dehydrogenase inhibitors (SDIs). The design concept included spawning of these templates to function as effective ligands to the catalytic zinc within the enzyme through incorporation of optimally substituted piperazino-triazine side chains so as to accommodate the active site in the enzyme for efficient binding. This strategy resulted in orally active SDIs, which penetrate key tissues, for example, sciatic nerve of chronically diabetic rats. The latter template led to the design of the title inhibitor, 33, which normalized the elevated sciatic nerve fructose by 96% at an oral dose of 10 mg/kg. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00490-5