1-(2-thianthrenyl)-2,4-dimethoxybenzene | 1271737-07-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二硫类化合物
• 英文名称: 1-(2-thianthrenyl)-2,4-dimethoxybenzene
• 英文别名: 2-(2,4-Dimethoxyphenyl)thianthrene
• CAS: 1271737-07-5
• 化学式: C₂₀H₁₆O₂S₂
• 分子量: 352.478
• InChiKey: HAUBOFLGYNIQCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-thianthrenyl)-2,4-dimethoxybenzene 在 sodium phosphate dibasic dodecahydrate 、 potassium nitrososulfonate 、 三溴化硼 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 38.0h， 生成 5-(2-thianthrenyl)-2-hydroxy-2,5-cyclohexadiene-1,4-dione
  参考文献：
  名称：

  Structure-based design, synthesis and preliminary anti-inflammatory activity of bolinaquinone analogues

  摘要：

  As a part of our drug discovery efforts we developed a series of simplified derivatives of bolinaquinone (BLQ), a hydroxyquinone marine metabolite, showing potent anti-inflammatory activity. Thirteen new hydroxyquinone derivatives closely related to BLQ were synthesized and tested on mouse macrophagelike RAW 264.7 cell line in order to investigate their ability to modulate the production of Prostaglandin E-2 (PGE(2)). This optimization process led to the identification of three strictly correlated compounds with comparable and higher inhibitory potency than BLQ on PGE2 production. To evaluate the affinity of BLQ and its analogues for h5PLA(2), surface plasmon resonance (SPR) experiments were performed. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.028
• 作为产物：
  描述：

  2,4-二甲氧基碘苯 、 噻蒽-2-硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 0.42h， 以77%的产率得到1-(2-thianthrenyl)-2,4-dimethoxybenzene
  参考文献：
  名称：

  Structure-based design, synthesis and preliminary anti-inflammatory activity of bolinaquinone analogues

  摘要：

  As a part of our drug discovery efforts we developed a series of simplified derivatives of bolinaquinone (BLQ), a hydroxyquinone marine metabolite, showing potent anti-inflammatory activity. Thirteen new hydroxyquinone derivatives closely related to BLQ were synthesized and tested on mouse macrophagelike RAW 264.7 cell line in order to investigate their ability to modulate the production of Prostaglandin E-2 (PGE(2)). This optimization process led to the identification of three strictly correlated compounds with comparable and higher inhibitory potency than BLQ on PGE2 production. To evaluate the affinity of BLQ and its analogues for h5PLA(2), surface plasmon resonance (SPR) experiments were performed. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.028

文献信息

• Structure-based design, synthesis and preliminary anti-inflammatory activity of bolinaquinone analogues
  作者：Carmen Petronzi、Rosanna Filosa、Antonella Peduto、Maria Chiara Monti、Luigi Margarucci、Antonio Massa、Simona Francesca Ercolino、Valentina Bizzarro、Luca Parente、Raffaele Riccio、Paolo de Caprariis

  DOI：10.1016/j.ejmech.2010.11.028

  日期：2011.2

  As a part of our drug discovery efforts we developed a series of simplified derivatives of bolinaquinone (BLQ), a hydroxyquinone marine metabolite, showing potent anti-inflammatory activity. Thirteen new hydroxyquinone derivatives closely related to BLQ were synthesized and tested on mouse macrophagelike RAW 264.7 cell line in order to investigate their ability to modulate the production of Prostaglandin E-2 (PGE(2)). This optimization process led to the identification of three strictly correlated compounds with comparable and higher inhibitory potency than BLQ on PGE2 production. To evaluate the affinity of BLQ and its analogues for h5PLA(2), surface plasmon resonance (SPR) experiments were performed. (C) 2010 Elsevier Masson SAS. All rights reserved.