N-[(4-bromonaphthalen-1-yl)sulfonyl]glycine | 905774-43-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[(4-bromonaphthalen-1-yl)sulfonyl]glycine
• 英文别名: 2-[(4-bromonaphthalen-1-yl)sulfonylamino]acetic acid
• CAS: 905774-43-8
• 化学式: C₁₂H₁₀BrNO₄S
• 分子量: 344.186
• InChiKey: JLDCMFXGZPSNPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(4-bromonaphthalen-1-yl)sulfonyl]glycine 在 吡啶 、 水 、 乙酸酐 、 氯乙酸 作用下， 反应 27.0h， 生成 1-[(4-bromo-1-naphthalenyl)sulfonyl]-2,4-imidazolidinedione
  参考文献：
  名称：

  Naphthalenylsulfonyl-hydantoins as aldose reductase inhibitors

  摘要：

  Accumulation of intracellular sorbitol, formed from glucose by aldose reductase, is believed to play an important role in the development of certain chronic complications of diabetes mellitus. Several 1-(naphthalenylsulfonyl)hydantoins inhibit aldose reductase isolated from bovine lens in vitro, and decrease galactitol formation in sciatic nerves of galactosemic rats in vivo. The 5-bromo analogue (entry 12, table I) was found to be the most orally active aldose reductase inhibitor of this series with an ED50 value of 8.1 mg/kg po. The 1-(naphthalenylsulfonyl)-2-thiohydantoin analogues with the exception of entry 11 (table I) which showed good in vivo activity, were either inactive or had only marginal activity.

  DOI：

  10.1016/0223-5234(91)90096-6
• 作为产物：
  描述：

  4-溴-1-萘磺酰氯 、 聚甘氨酸 在 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 N-[(4-bromonaphthalen-1-yl)sulfonyl]glycine
  参考文献：
  名称：

  Naphthalenylsulfonyl-hydantoins as aldose reductase inhibitors

  摘要：

  Accumulation of intracellular sorbitol, formed from glucose by aldose reductase, is believed to play an important role in the development of certain chronic complications of diabetes mellitus. Several 1-(naphthalenylsulfonyl)hydantoins inhibit aldose reductase isolated from bovine lens in vitro, and decrease galactitol formation in sciatic nerves of galactosemic rats in vivo. The 5-bromo analogue (entry 12, table I) was found to be the most orally active aldose reductase inhibitor of this series with an ED50 value of 8.1 mg/kg po. The 1-(naphthalenylsulfonyl)-2-thiohydantoin analogues with the exception of entry 11 (table I) which showed good in vivo activity, were either inactive or had only marginal activity.

  DOI：

  10.1016/0223-5234(91)90096-6

文献信息

• Naphthalenylsulfonyl-hydantoins as aldose reductase inhibitors
  作者：MS Malamas、K Sestanj、J Millen

  DOI：10.1016/0223-5234(91)90096-6

  日期：1991.6

  Accumulation of intracellular sorbitol, formed from glucose by aldose reductase, is believed to play an important role in the development of certain chronic complications of diabetes mellitus. Several 1-(naphthalenylsulfonyl)hydantoins inhibit aldose reductase isolated from bovine lens in vitro, and decrease galactitol formation in sciatic nerves of galactosemic rats in vivo. The 5-bromo analogue (entry 12, table I) was found to be the most orally active aldose reductase inhibitor of this series with an ED50 value of 8.1 mg/kg po. The 1-(naphthalenylsulfonyl)-2-thiohydantoin analogues with the exception of entry 11 (table I) which showed good in vivo activity, were either inactive or had only marginal activity.