7-methyl-3-(2-naphthalenylsulfonyl)-1,3-diazaspiro[4.5]decane-2,4-dione | 1361251-50-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-methyl-3-(2-naphthalenylsulfonyl)-1,3-diazaspiro[4.5]decane-2,4-dione
• 英文别名: 7-methyl-3-naphthalen-2-ylsulfonyl-1,3-diazaspiro[4.5]decane-2,4-dione
• CAS: 1361251-50-4
• 化学式: C₁₉H₂₀N₂O₄S
• 分子量: 372.445
• InChiKey: NLHHAZPHPLFWNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  91.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲基环己酮 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 15.0h， 生成 7-methyl-3-(2-naphthalenylsulfonyl)-1,3-diazaspiro[4.5]decane-2,4-dione
  参考文献：
  名称：

  Synthesis, characterization, and hypoglycemic activity of 3-(arylsulfonyl)spiroimidazolidine-2,4-diones

  摘要：

  Spiroimidazolidine-2,4-diones were prepared from methylcyclohexanones by the Bucherer-Bergs reaction. Synthesis of the target 3-(arylsulfonyl)spiroimidazolidine-2,4-diones was achieved by reaction of arylsulfonyl chlorides with corresponding spiroimidazolidine-2,4-diones. The synthesis was confirmed by spectroanalytical techniques and the crystal structure of 3-(4-methoxyphenylsulfonyl)-6-methyl-1,3-diazaspiro[4.5]decane-2,4-dione, and the purity was checked by GC-MS analysis. The in-vivo hypoglycemic potential of 6-methyl-, 7-methyl-, and 8-methyl-3-(4-methylphenylsulfonyl)-1,3-diazaspiro[4.5]decane-2,4-dione was investigated on male albino rats. The screened compounds were found to have excellent hypoglycemic activity. 6-Methyl-3-(4-methylphenylsulfonyl)-1,3-diazaspiro[4.5]decane-2,4-dione was found highly active, reducing the blood glucose level by 60.79% compared with 41.60% by the standard (glipizide) at a dose level of 100 mg/kg of the mice body weight. The 8-methyl isomer was also more potent than the standard, with 48.56% reduction in blood glucose level.

  DOI：

  10.1007/s00706-011-0600-9