N-(4-(phenylsulfonyl)phenyl)-5-nitrofuran-2-carboxamide

• 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-(phenylsulfonyl)phenyl)-5-nitrofuran-2-carboxamide
• 英文别名: SID 117695372；N-[4-(benzenesulfonyl)phenyl]-5-nitrofuran-2-carboxamide
• 化学式: C₁₇H₁₂N₂O₆S
• 分子量: 372.358
• InChiKey: AJZUUIHIVCVVNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-硝基-2-糠酰氯 、 4-(苯基磺酰基)苯胺 以 乙腈 为溶剂， 反应 0.33h， 以61%的产率得到N-(4-(phenylsulfonyl)phenyl)-5-nitrofuran-2-carboxamide
  参考文献：
  名称：

  Discovery of Sulfonamidebenzamides as Selective Apoptotic CHOP Pathway Activators of the Unfolded Protein Response

  摘要：

  Cellular proteins that fail to fold properly result in inactive or disfunctional proteins that can have toxic functions. The unfolded protein response (UPR) is a two-tiered cellular mechanism initiated by eukaryotic cells that have accumulated misfolded proteins within the endoplasmic reticulum (ER). An adaptive pathway facilitates the clearance of the undesired proteins; however, if overwhelmed, cells trigger apoptosis by upregulating transcription factors such as C/EBP-homologous protein (CHOP). A high throughput screen was performed directed at identifying compounds that selectively upregulate the apoptotic CHOP pathway while avoiding adaptive signaling cascades, resulting in a sulfonamidebenzamide chemotype that was optimized. These efforts produced a potent and selective CHOP inducer (AC(50) = 0.8 mu M; XBP1 > 80 mu M), which was efficacious in both mouse embryonic fibroblast cells and a human oral squamous cell cancer cell line, and demonstrated antiproliferative effects for multiple cancer cell lines in the NCI-60 panel.

  DOI：

  10.1021/ml5003234

文献信息

• COMPOUNDS AND METHODS FOR ACTIVATING THE APOPTOTIC ARM OF THE UNFOLDED PROTEIN RESPONSE
  申请人：University of Kansas

  公开号：US20150203477A1

  公开（公告）日：2015-07-23

  N-substituted sulfonylphenyl-5-nitrofuranyl-2-carboxamide derived compounds, which selectively activate the apoptotic, but not the adaptive arm, of the Unfolded Protein Response are provides as is their use in the treatment of diseases such as diabetes, Alzheimer's, Parkinson's, hemophilia, lysosomal storage diseases and cancer.

  提供了N-取代磺酰基苯基-5-硝基呋喃-2-羧酰胺衍生物化合物，其选择性激活蛋白质错配反应的凋亡分支而非适应性分支，并且可以用于治疗糖尿病、阿尔茨海默病、帕金森病、血友病、溶酶体贮积病和癌症。
• US9732067B2
  申请人：——

  公开号：US9732067B2

  公开（公告）日：2017-08-15