3,5-bis[(4-fluorophenyl)methylidene]thian-4-one | 1620205-31-3

• 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: 3,5-bis[(4-fluorophenyl)methylidene]thian-4-one
• CAS: 1620205-31-3
• 化学式: C₁₉H₁₄F₂OS
• 分子量: 328.382
• InChiKey: UJSTXJAMZWCSHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3,5-bis[(4-fluorophenyl)methylidene]thian-4-one 在 双氧水 、 溶剂黄146 作用下， 以51.9%的产率得到3,5-bis-(4-fluorobenzylidene)-1,1-dioxotetrahydro-1λ6-thiopyran-4-one
  参考文献：
  名称：

  Synthesis and Evaluation of Bisbenzylidenedioxotetrahydrothiopranones as Activators of Endoplasmic Reticulum (ER) Stress Signaling Pathways and Apoptotic Cell Death in Acute Promyelocytic Leukemic Cells

  摘要：

  Curcumin is known to trigger ER-stress induced cell death of acute promyelocytic leukemic (APL) cells by intercepting the degradation of nuclear co-repressor (N-CoR) protein which has a key role in the pathogenesis of APL. Replacing the heptadienedione moiety of curcumin with a monocarbonyl cross-conjugated dienone embedded in a tetrahydrothiopyranone dioxide ring resulted in thiopyranone dioxides that were more resilient to hydrolysis and had greater growth inhibitory activities than curcumin on APL cells. Several members intercepted the degradation of misfolded N-CoR and triggered the signaling cascade in the unfolded protein response (UPR) which led to apoptotic cell death. Microarray analysis showed that genes involved in protein processing pathways that were germane to the activation of the UPR were preferentially up-regulated in treated APL cells, supporting the notion that the UPR was a consequential mechanistic pathway affected by thiopyranone dioxides. The Michael acceptor reactivity of the scaffold may have a role in exacerbating ER stress in APL cells.

  DOI：

  10.1021/jm401352a
• 作为产物：
  描述：

  四氢噻喃-4-酮 、 对氟苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 3,5-bis[(4-fluorophenyl)methylidene]thian-4-one
  参考文献：
  名称：

  Synthesis and Evaluation of Bisbenzylidenedioxotetrahydrothiopranones as Activators of Endoplasmic Reticulum (ER) Stress Signaling Pathways and Apoptotic Cell Death in Acute Promyelocytic Leukemic Cells

  摘要：

  Curcumin is known to trigger ER-stress induced cell death of acute promyelocytic leukemic (APL) cells by intercepting the degradation of nuclear co-repressor (N-CoR) protein which has a key role in the pathogenesis of APL. Replacing the heptadienedione moiety of curcumin with a monocarbonyl cross-conjugated dienone embedded in a tetrahydrothiopyranone dioxide ring resulted in thiopyranone dioxides that were more resilient to hydrolysis and had greater growth inhibitory activities than curcumin on APL cells. Several members intercepted the degradation of misfolded N-CoR and triggered the signaling cascade in the unfolded protein response (UPR) which led to apoptotic cell death. Microarray analysis showed that genes involved in protein processing pathways that were germane to the activation of the UPR were preferentially up-regulated in treated APL cells, supporting the notion that the UPR was a consequential mechanistic pathway affected by thiopyranone dioxides. The Michael acceptor reactivity of the scaffold may have a role in exacerbating ER stress in APL cells.

  DOI：

  10.1021/jm401352a

文献信息

• Three-Component [3 + 3] Heterocyclizations for Flexible Synthesis of Bicyclic Fused Pyridines Under Microwave Irradiation
  作者：Jie Liu、Yuan-Yuan Pan、Li-Yuan Xue、Wen-Juan Hao、Jin-Peng Zhang、Shu-Liang Wang、Bo Jiang

  DOI：10.1002/jhet.2438

  日期：2016.7

  Three‐component [3 + 3] heterocyclizations have been established under microwave irradiation, providing a flexible synthetic approach toward bicyclic fused pyridines. 3,5‐Dibenzylidenedihydro‐2H‐pyran‐4(3H)‐ones were subject with malononitrile and aromatic amines in cosolvent of HOAc and N,N‐dimethylformamide, affording 10 examples of pyrano[4,3‐b]pyridine derivatives in good to excellent yields. Similarly

  在微波辐射下已经建立了三组分[3 + 3]杂环，为双环稠合吡啶提供了灵活的合成方法。3,5-二苄基二氢-2 H-吡喃-4（3 H）-酮与丙二腈和芳香胺在HOAc和N，N-二甲基甲酰胺的共溶剂中共存，提供了10个吡喃并[4,3- b ]吡啶衍生物实例高产到高产。同样，使用硫拴系杂环作为反应伙伴，获得了七个硫吡喃并[4,3- b ]吡啶衍生物的实例。