o-dodecyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide | 1296884-94-0

• 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: o-dodecyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide
• 英文别名: ortho-Dodecyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide；2-dodecyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide
• CAS: 1296884-94-0
• 化学式: C₂₀H₃₁N₃O₂S₂
• 分子量: 409.617
• InChiKey: HTPZUHITNABZOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-十二烷基酚 在 吡啶 、 甲酸 、 双氧水 、 sodium hydride 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 o-dodecyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide
  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。
• US8420678B2
  申请人：——

  公开号：US8420678B2

  公开（公告）日：2013-04-16
• US8962663B2
  申请人：——

  公开号：US8962663B2

  公开（公告）日：2015-02-24
• US9320734B2
  申请人：——

  公开号：US9320734B2

  公开（公告）日：2016-04-26