2-(azetidine-1-sulfonyl)-1-phenyl-ethanone | 845281-74-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(azetidine-1-sulfonyl)-1-phenyl-ethanone
• 英文别名: 2-(azetidin-1-ylsulfonyl)-1-phenylethanone
• CAS: 845281-74-5
• 化学式: C₁₁H₁₃NO₃S
• 分子量: 239.295
• InChiKey: OZQYMUQBDMIKHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(azetidine-1-sulfonyl)-1-phenyl-ethanone 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以75%的产率得到1-(2-phenyl-ethynesulfonyl)-azetidine
  参考文献：
  名称：

  Hepatoselectivity of statins: Design and synthesis of 4-sulfamoyl pyrroles as HMG-CoA reductase inhibitors

  摘要：

  4-Sulfamoyl pyrroles were designed as novel hepatoselective HMG-CoA reductase inhibitors (statins) to reduce myalgia, a statin-induced adverse effect. The compounds were prepared via a [3 + 2] cycloaddition of a Munchnone with a sulfonamide-substituted alkyne. We identified compounds with greater selectivity for hepatocytes compared to L6-myocytes than rosuvastatin and atorvastatin. There was an inverse correlation of myocyte potencies and ClogP values. A number of analogs were effective at reducing cholesterol in acute and chronic in vivo models but they lacked sufficient chronic in vivo activity to warrant further development. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.124
• 作为产物：
  描述：

  苯甲酸甲酯 、 1-(甲基磺酰基)吖丁啶 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 2-(azetidine-1-sulfonyl)-1-phenyl-ethanone
  参考文献：
  名称：

  [EN] PYRROLE-BASED HMG-COA REDUCTASE INHIBITORS
  [FR] INHIBITEURS NOUVEAUX DE L'HMG-COA REDUCTASE A BASE DE PYRROLE

  摘要：

  公开号：

  WO2005014539A3

文献信息

• Novel pyrroles and imidazoles
  申请人：Bolton Louis Gary

  公开号：US20060287378A1

  公开（公告）日：2006-12-21

  Novel imidazoles and novel pyrroles are provided. Also provided are pharmaceutical compositions, methods of making and methods of using the compounds.

  本发明提供了新型咪唑和新型吡咯。同时，还提供了制药组合物、制备方法和使用该化合物的方法。
• Novel pyrrole-based HMG-CoA reductase inhibitors
  申请人：Kennedy Michael Robert

  公开号：US20050043364A1

  公开（公告）日：2005-02-24

  50 HMGCo-A reductase inhibitor compounds useful as hypocholesterolemic and hypolipidemic compounds are provided. Also provided are pharmaceutical compositions of the compounds. Methods of making and methods of using the compounds are also provided.
• US7250444B2
  申请人：——

  公开号：US7250444B2

  公开（公告）日：2007-07-31
• Hepatoselectivity of statins: Design and synthesis of 4-sulfamoyl pyrroles as HMG-CoA reductase inhibitors
  作者：William K.C. Park、Robert M. Kennedy、Scott D. Larsen、Steve Miller、Bruce D. Roth、Yuntao Song、Bruce A. Steinbaugh、Kevin Sun、Bradley D. Tait、Mark C. Kowala、Bharat K. Trivedi、Bruce Auerbach、Valerie Askew、Lisa Dillon、Jeffrey C. Hanselman、Zhiwu Lin、Gina H. Lu、Andrew Robertson、Catherine Sekerke

  DOI：10.1016/j.bmcl.2007.11.124

  日期：2008.2

  4-Sulfamoyl pyrroles were designed as novel hepatoselective HMG-CoA reductase inhibitors (statins) to reduce myalgia, a statin-induced adverse effect. The compounds were prepared via a [3 + 2] cycloaddition of a Munchnone with a sulfonamide-substituted alkyne. We identified compounds with greater selectivity for hepatocytes compared to L6-myocytes than rosuvastatin and atorvastatin. There was an inverse correlation of myocyte potencies and ClogP values. A number of analogs were effective at reducing cholesterol in acute and chronic in vivo models but they lacked sufficient chronic in vivo activity to warrant further development. (C) 2007 Elsevier Ltd. All rights reserved.
• [EN] PYRROLE-BASED HMG-COA REDUCTASE INHIBITORS<br/>[FR] INHIBITEURS NOUVEAUX DE L'HMG-COA REDUCTASE A BASE DE PYRROLE
  申请人：WARNER LAMBERT CO

  公开号：WO2005014539A3

  公开（公告）日：2005-05-12