N-[2-(2-thienyl)ethyl]-5-dimethylamino-1-naphthalenesulfon-amide | 1377924-27-0

• 英文名称: N-[2-(2-thienyl)ethyl]-5-dimethylamino-1-naphthalenesulfon-amide
• CAS: 1377924-27-0
• 化学式: C₁₈H₂₀N₂O₂S₂
• 分子量: 360.501
• InChiKey: IIWYBLLOEXPYHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.41
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-[2-(2-thienyl)ethyl]-5-dimethylamino-1-naphthalenesulfon-amide 在 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-[2-(2-thienyl)ethyl]-N-[(5-dimethylamino-1 naphthalenyl)sulfonyl]glycine
  参考文献：
  名称：

  Progresses in the pursuit of aldose reductase inhibitors: The structure-based lead optimization step

  摘要：

  Aldose reductase (ALR2) is a crucial enzyme in the development of the major complications of diabetes mellitus. Very recently it has been demonstrated that the ARL2 inhibitor, fidarestat, significantly prevents inflammatory signals (TNF-alpha, LPS) that cause cancer (colon, breast, prostate and lung), metastasis, asthma, and other inflammatory diseases. Currently, fidarestat is in phase Ill clinical trial for diabetic neuropathy and was found to be safe. Thus the finding of novel, potent ARL2 inhibitors is today more than in the past in great demand as they can pave the way for a novel therapeutic approach for a number of diseases besides the diabetes. Herein, starting from the virtual screening-derived ALR2 inhibitor S12728 (1), a rational receptor-based lead optimization has been undertaken. The design and synthetic efforts here reported led to the discovery of several new compounds endowed with low micromolar/submicromolar activities. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.045
• 作为产物：
  描述：

  噻吩乙胺 、 丹酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到N-[2-(2-thienyl)ethyl]-5-dimethylamino-1-naphthalenesulfon-amide
  参考文献：
  名称：

  Progresses in the pursuit of aldose reductase inhibitors: The structure-based lead optimization step

  摘要：

  Aldose reductase (ALR2) is a crucial enzyme in the development of the major complications of diabetes mellitus. Very recently it has been demonstrated that the ARL2 inhibitor, fidarestat, significantly prevents inflammatory signals (TNF-alpha, LPS) that cause cancer (colon, breast, prostate and lung), metastasis, asthma, and other inflammatory diseases. Currently, fidarestat is in phase Ill clinical trial for diabetic neuropathy and was found to be safe. Thus the finding of novel, potent ARL2 inhibitors is today more than in the past in great demand as they can pave the way for a novel therapeutic approach for a number of diseases besides the diabetes. Herein, starting from the virtual screening-derived ALR2 inhibitor S12728 (1), a rational receptor-based lead optimization has been undertaken. The design and synthetic efforts here reported led to the discovery of several new compounds endowed with low micromolar/submicromolar activities. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.045