N-(4-(N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)acetamide | 432539-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-(N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)acetamide
• 英文别名: N-[4-(5-tert-Butyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-acetamide；N-[4-[(5-tert-butyl-1,3,4-thiadiazol-2-yl)sulfamoyl]phenyl]acetamide
• CAS: 432539-49-6
• 化学式: C₁₄H₁₈N₄O₃S₂
• 分子量: 354.454
• InChiKey: QUQBPXUDNLUFHV-UHFFFAOYSA-N

物化性质

• 密度：
  1.394±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(4-(N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)acetamide 在 吡啶 、 盐酸 作用下， 以 水 为溶剂， 反应 1.5h， 生成 N-(4-(N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)decanamide
  参考文献：
  名称：

  Development of sulfonamide AKT PH domain inhibitors

  摘要：

  Disruption of the phosphatidylinositol 3-kinase/AKT signaling pathway can lead to apoptosis in cancer cells. Previously we identified a lead sulfonamide that selectively bound to the pleckstrin homology (PH) domain of AKT and induced apoptosis when present at low micromolar concentrations. To examine the effects of structural modification, a set of sulfonamides related to the lead compound was designed, synthesized, and tested for binding to the expressed PH domain of AKT using a surface plasmon resonance-based competitive binding assay. Cellular activity was determined by means of an assay for pAKT production and a cell killing assay using BxPC-3 cells. The most active compounds in the set are lipophilic and possess an aliphatic chain of the proper length. Results were interpreted with the aid of computational modeling. This paper represents the first structure-activity relationship (SAR) study of a large family of AKT PH domain inhibitors. Information obtained will be used in the design of the next generation of inhibitors of AKT PH domain function. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.049
• 作为产物：
  描述：

  2-氨基-5-叔-丁基-1,3,4-噻二唑 、 对乙酰胺基苯磺酰氯 在 吡啶 作用下， 反应 1.0h， 以84%的产率得到N-(4-(N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)acetamide
  参考文献：
  名称：

  Development of sulfonamide AKT PH domain inhibitors

  摘要：

  Disruption of the phosphatidylinositol 3-kinase/AKT signaling pathway can lead to apoptosis in cancer cells. Previously we identified a lead sulfonamide that selectively bound to the pleckstrin homology (PH) domain of AKT and induced apoptosis when present at low micromolar concentrations. To examine the effects of structural modification, a set of sulfonamides related to the lead compound was designed, synthesized, and tested for binding to the expressed PH domain of AKT using a surface plasmon resonance-based competitive binding assay. Cellular activity was determined by means of an assay for pAKT production and a cell killing assay using BxPC-3 cells. The most active compounds in the set are lipophilic and possess an aliphatic chain of the proper length. Results were interpreted with the aid of computational modeling. This paper represents the first structure-activity relationship (SAR) study of a large family of AKT PH domain inhibitors. Information obtained will be used in the design of the next generation of inhibitors of AKT PH domain function. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.049

文献信息

• PHARMACEUTICAL COMPOSITIONS AND FORMULATIONS INCLUDING INHIBITORS OF THE PLECKSTRIN HOMOLOGY DOMAIN AND METHODS FOR USING SAME
  申请人：Kirkpatrick D. Lynn

  公开号：US20120189670A1

  公开（公告）日：2012-07-26

  Pleckstrin homology domain binding compounds, pharmaceutical compositions including such compounds, and methods for their use are described herein.

  本文描述了与Pleckstrin同源结构域结合的化合物，包括这些化合物的药物组合物，以及其使用方法。
• SMALL MOLECULE INHIBITORS OF THE PLECKSTRIN HOMOLOGY DOMAIN AND METHODS FOR USING SAME
  申请人：Mahadevan Daruka

  公开号：US20110144066A1

  公开（公告）日：2011-06-16

  Pleckstrin homology domain binding compounds, pharmaceutical compositions including such compounds, and methods for their use are described herein.

  本文描述了Pleckstrin homology domain结合化合物、包括这些化合物的制药组合物以及它们的使用方法。
• Small molecule inhibitors of the pleckstrin homology domain and methods for using same
  申请人：Mahadevan Daruka

  公开号：US08420678B2

  公开（公告）日：2013-04-16

  Pleckstrin homology domain binding compounds, pharmaceutical compositions including such compounds, and methods for their use are described herein.

  本文描述了与Pleckstrin同源结构域结合的化合物、包括此类化合物的制药组合物以及使用它们的方法。
• Small molecule inhibitors of the pleckstrin homology domain and method for using same
  申请人：The Board of Regents of the University of Texas System

  公开号：EP2428504A1

  公开（公告）日：2012-03-14

  Pleckstrin homology domain binding compounds, pharmaceutical compositions including such compounds, and methods for their use are described herein

  本文描述了 Pleckstrin 同源结构域结合化合物、包括此类化合物的药物组合物及其使用方法
• [EN] SMALL MOLECULE INHIBITORS OF THE PLECKSTRIN HOMOLOGY DOMAIN AND METHODS FOR USING SAME<br/>[FR] INHIBITEURS DE PETITES MOLÉCULES DU DOMAINE D'HOMOLOGIE DE LA PLECKSTRINE, ET LEURS MÉTHODES D'UTILISATION
  申请人：UNIV TEXAS

  公开号：WO2009129267A3

  公开（公告）日：2010-02-04