(Z)-1-((3αR,7αR)-5-oxo-7α-phenyl-4,5-dihydrobenzofuran-3(2H,3αH,7αH)-ylidene)ethyl acetate | 1375111-58-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (Z)-1-((3αR,7αR)-5-oxo-7α-phenyl-4,5-dihydrobenzofuran-3(2H,3αH,7αH)-ylidene)ethyl acetate
• 英文别名: [(1Z)-1-[(3aR,7aR)-5-oxo-7a-phenyl-3a,4-dihydro-1-benzofuran-3-ylidene]ethyl] acetate
• CAS: 1375111-58-2
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: DPTONBAWVXDDME-QYWGPIJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(but-2-yn-1-yloxy)-[1,1'-biphenyl]-4(1H)-one 、 溶剂黄146 在 palladium diacetate 、 (1R,9R,1'R,9'R)-10,10,10',10'-tetramethyl[5,5']bi[6-azatricyclo[7.1.1.0(2,7)]undecyl]-2(7),3,5,2',4',6'-hexaene 作用下， 反应 16.0h， 生成 (Z)-1-((3αS,7αS)-5-oxo-7α-phenyl-4,5-dihydrobenzofuran-3(2H,3αH,7αH)-ylidene)ethyl acetate 、 (Z)-1-((3αR,7αR)-5-oxo-7α-phenyl-4,5-dihydrobenzofuran-3(2H,3αH,7αH)-ylidene)ethyl acetate
  参考文献：
  名称：

  Bicyclic Cyclohexenones as Inhibitors of NF-κB Signaling

  摘要：

  A series of structurally simplified cryptocaryone analogues were synthesized by a facile Pd-catalyzed acetoxylation of alkyne-tethered cyclohexadienones and evaluated as inhibitors of NF-kappa B signaling. Compounds 10 and 11 were found to possess low micromolar inhibitory properties toward induced NF-kappa B activity by blocking p50/p65 nuclear protein through a covalent inhibition mechanism. Both compounds were: able to inhibit NF-kappa B-induced IL-8 expression and exhibited antiproliferative activity against two model cancer cell lines. These analogues constitute a promising new scaffolc. for the development of novel NF-kappa B inhibitors and anticancer agents.

  DOI：

  10.1021/ml300034a

文献信息

• CN117003717
  申请人：——

  公开号：——

  公开（公告）日：——
• Bicyclic Cyclohexenones as Inhibitors of NF-κB Signaling
  作者：Joseph K. Hexum、Rodolfo Tello-Aburto、Nicholas B. Struntz、Andrew M. Harned、Daniel A. Harki

  DOI：10.1021/ml300034a

  日期：2012.6.14

  A series of structurally simplified cryptocaryone analogues were synthesized by a facile Pd-catalyzed acetoxylation of alkyne-tethered cyclohexadienones and evaluated as inhibitors of NF-kappa B signaling. Compounds 10 and 11 were found to possess low micromolar inhibitory properties toward induced NF-kappa B activity by blocking p50/p65 nuclear protein through a covalent inhibition mechanism. Both compounds were: able to inhibit NF-kappa B-induced IL-8 expression and exhibited antiproliferative activity against two model cancer cell lines. These analogues constitute a promising new scaffolc. for the development of novel NF-kappa B inhibitors and anticancer agents.