2-(2,6-dioxotetrahydro-2H-pyran-3-yl)-1H-benzo[f]isoindole-1,3(2H)-dione | 458151-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(2,6-dioxotetrahydro-2H-pyran-3-yl)-1H-benzo[f]isoindole-1,3(2H)-dione
• 英文别名: 2-(2,6-Dioxooxan-3-yl)benzo[f]isoindole-1,3-dione
• CAS: 458151-04-7
• 化学式: C₁₇H₁₁NO₅
• 分子量: 309.278
• InChiKey: MCOMQMLKHBBWHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2,6-dioxotetrahydro-2H-pyran-3-yl)-1H-benzo[f]isoindole-1,3(2H)-dione 在 氨 、 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.5h， 以91%的产率得到5-amino-2-(1,3-dioxo-1H-benzo[f]isoindol-2(3H)-yl)-5-oxopentanoic acid
  参考文献：
  名称：

  Discovering a new analogue of thalidomide which may be used as a potent modulator of TNF-α production

  摘要：

  A new series of imide derivatives related to thalidomide were synthesized and evaluated as modulators of TNF-alpha production. These derivatives enhance TNF-a production using human leukemia HL-60 cells induced with 12-O-tetradecanoylphorbol 13-acetate (TPA), while inhibiting TNF-alpha production induced with okadaic acid (OA) in the same cell line. The diphenylmaleimide derivative 2f, was found to be the most active product, producing a strong modulation of the cytokine level. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.03.018
• 作为产物：
  描述：

  2，3-萘二酐 、 L-谷氨酸 在 吡啶 、 乙酸酐 作用下， 反应 0.5h， 以75%的产率得到2-(2,6-dioxotetrahydro-2H-pyran-3-yl)-1H-benzo[f]isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Discovering a new analogue of thalidomide which may be used as a potent modulator of TNF-α production

  摘要：

  A new series of imide derivatives related to thalidomide were synthesized and evaluated as modulators of TNF-alpha production. These derivatives enhance TNF-a production using human leukemia HL-60 cells induced with 12-O-tetradecanoylphorbol 13-acetate (TPA), while inhibiting TNF-alpha production induced with okadaic acid (OA) in the same cell line. The diphenylmaleimide derivative 2f, was found to be the most active product, producing a strong modulation of the cytokine level. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.03.018

文献信息

• Discovering a new analogue of thalidomide which may be used as a potent modulator of TNF-α production
  作者：Miguel Fernández Braña、Nuria Acero、Loreto Añorbe、Dolores Muñoz Mingarro、Francisco Llinares、Gema Domínguez

  DOI：10.1016/j.ejmech.2009.03.018

  日期：2009.9

  A new series of imide derivatives related to thalidomide were synthesized and evaluated as modulators of TNF-alpha production. These derivatives enhance TNF-a production using human leukemia HL-60 cells induced with 12-O-tetradecanoylphorbol 13-acetate (TPA), while inhibiting TNF-alpha production induced with okadaic acid (OA) in the same cell line. The diphenylmaleimide derivative 2f, was found to be the most active product, producing a strong modulation of the cytokine level. (C) 2009 Elsevier Masson SAS. All rights reserved.