| 1577214-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• CAS: 1577214-97-1
• 化学式: C₂₀H₂₀N₂O₅S₂
• 分子量: 432.521
• InChiKey: QIAYCMVCCVOVMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  102.43
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  、 二乙胺 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N,N-diethyl-2-{2-[(1-naphthylsulfonyl)amino]-1,3-thiazol-4-yl}acetamide
  参考文献：
  名称：

  Synthesis of 2-{2-[(α/β-naphthalen-1-ylsulfonyl)amino]-1,3-thiazol-4-yl} acetamides with 11β-hydroxysteroid dehydrogenase inhibition and in combo antidiabetic activities

  摘要：

  Compounds 1-10 were designed using a bioisosteric approach and were prepared using a short synthetic route. The in vitro inhibitory activity of the compounds against 11 beta-hydroxysteroid dehydrogenase type 1 (11 beta-HSD1) was evaluated. Compounds 5 (alpha-series) and 10 (beta-series) had a moderate inhibitory enzyme activity (55.26% and 67.03% inhibition at 10 mu M, respectively) and were as active as BVT.14225 (positive control). Both compounds have a piperidine ring in their structure, but the most active (10) was selected to establish its in vivo antidiabetic effect using a non insulin-dependent diabetes mellitus rat model. The antidiabetic activity of compound 10 was determined at 50 mg/kg single dose in an acute model, and also by short term sub-chronic administration for 5 days. The results indicated a significant decrease of plasma glucose levels, similar than BVT.14225. Additionally, a molecular docking of the most active compounds of each series into the ligand binding pocket of one subunit of human 11 beta-HSD1 was performed. In this model the oxygen atom of the sulfonamide make hydrogen bond interactions with the catalytic residues Ser170 and Ala172. We also observed important pi-pi interactions between the naphthyl group and Tyr177. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.042
• 作为产物：
  描述：

  2-氨基-4-噻唑乙酸乙酯 在 4-二甲氨基吡啶 、 水 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 173.25h， 生成
  参考文献：
  名称：

  Synthesis of 2-{2-[(α/β-naphthalen-1-ylsulfonyl)amino]-1,3-thiazol-4-yl} acetamides with 11β-hydroxysteroid dehydrogenase inhibition and in combo antidiabetic activities

  摘要：

  Compounds 1-10 were designed using a bioisosteric approach and were prepared using a short synthetic route. The in vitro inhibitory activity of the compounds against 11 beta-hydroxysteroid dehydrogenase type 1 (11 beta-HSD1) was evaluated. Compounds 5 (alpha-series) and 10 (beta-series) had a moderate inhibitory enzyme activity (55.26% and 67.03% inhibition at 10 mu M, respectively) and were as active as BVT.14225 (positive control). Both compounds have a piperidine ring in their structure, but the most active (10) was selected to establish its in vivo antidiabetic effect using a non insulin-dependent diabetes mellitus rat model. The antidiabetic activity of compound 10 was determined at 50 mg/kg single dose in an acute model, and also by short term sub-chronic administration for 5 days. The results indicated a significant decrease of plasma glucose levels, similar than BVT.14225. Additionally, a molecular docking of the most active compounds of each series into the ligand binding pocket of one subunit of human 11 beta-HSD1 was performed. In this model the oxygen atom of the sulfonamide make hydrogen bond interactions with the catalytic residues Ser170 and Ala172. We also observed important pi-pi interactions between the naphthyl group and Tyr177. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.042