ethyl {2-[(1-naphthylsulfonyl)amino]-1,3-thiazol-4-yl}acetate | 1262723-80-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl {2-[(1-naphthylsulfonyl)amino]-1,3-thiazol-4-yl}acetate
• 英文别名: ethyl 2-[2-(naphthalen-1-ylsulfonylamino)-1,3-thiazol-4-yl]acetate
• CAS: 1262723-80-7；376637-51-3
• 化学式: C₁₇H₁₆N₂O₄S₂
• 分子量: 376.457
• InChiKey: OBFRWCVXUAAEQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl {2-[(1-naphthylsulfonyl)amino]-1,3-thiazol-4-yl}acetate 在 水 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 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
• 作为产物：
  描述：

  2-氨基-4-噻唑乙酸乙酯 、 1-萘磺酰氯 在 crude product 作用下， 生成 ethyl {2-[(1-naphthylsulfonyl)amino]-1,3-thiazol-4-yl}acetate
  参考文献：
  名称：

  INHIBITORS OF 11-BETA-HYDROXY STERIOD DEHYDROGENASE TYPE 1

  摘要：

  本发明涉及公式（II）的化合物，以及包含这些化合物的制药组合物，它们的制备过程，以及这些化合物在医学上的使用和用于制备对人类11-β-羟基类固醇脱氢酶1型酶起作用的药物。

  公开号：

  US20100113435A1

文献信息

• [EN] INHIBITORS OF 11-BETA-HYDROXY STEROID DEHYDROGENASE TYPE 1<br/>[FR] INHIBITEURS DE 11-BETA-HYDROXY-STEROIDE-DESHYDROGENASE DE TYPE 1
  申请人：BIOVITRUM AB

  公开号：WO2001090090A1

  公开（公告）日：2001-11-29

  The present invention relates to compounds with the formula (II) and also to pharmaceutical compositions comprising the compounds, to processes for their preparation, as well as to the use of thecompounds in medicine and for the preparation of a medicament which acts on the human 11-β-hydroxysteroid dehydrogenase type 1 enzyme.

  本发明涉及式（II）的化合物，以及包含该化合物的药物组合物，以及其制备过程，以及化合物在医学上的应用以及用于制备对人类11-β-羟基类固醇脱氢酶1型酶有作用的药物。
• Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1
  申请人：——

  公开号：US20040224996A1

  公开（公告）日：2004-11-11

  The present invention relates to compounds with the formula (II) and also to pharmaceutical compositions comprising the compounds, to processes for their preparation, as well as to the use of the compounds in medicine and for the preparation of a medicament which acts on the human 11-&bgr;-hydroxysteroid dehydrogenase type 1 enzyme. 1

  本发明涉及式（II）的化合物，以及包含该化合物的制药组合物，其制备过程，以及在医学上使用该化合物以及用于制备对人体11-β-羟基类固醇脱氢酶1型酶起作用的药物。
• INHIBITORS OF 11-BETA-HYDROXY STERIOD DEHYDROGENASE TYPE 1
  申请人：BARF Tjeerd

  公开号：US20100113435A1

  公开（公告）日：2010-05-06

  The present invention relates to compounds with the formula (II) and also to pharmaceutical compositions comprising the compounds, to processes for their preparation, as well as to the use of the compounds in medicine and for the preparation of a medicament which acts on the human 11-β-hydroxysteroid dehydrogenase type 1 enzyme.

  本发明涉及公式（II）的化合物，以及包含这些化合物的制药组合物，它们的制备过程，以及这些化合物在医学上的使用和用于制备对人类11-β-羟基类固醇脱氢酶1型酶起作用的药物。
• INHIBITORS OF 11-BETA-HYDROXY STEROID DEHYDROGENASE TYPE 1
  申请人：BIOVITRUM AB

  公开号：EP1283831A1

  公开（公告）日：2003-02-19
• US7618961B2
  申请人：——

  公开号：US7618961B2

  公开（公告）日：2009-11-17