5-amino-2-(2,6-dioxopiperidin-3-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione | 458151-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 5-amino-2-(2,6-dioxopiperidin-3-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 5-amino-2-(2,6-dioxopiperidin-3-yl)benzo[de]isoquinoline-1,3-dione
• CAS: 458151-38-7
• 化学式: C₁₇H₁₃N₃O₄
• 分子量: 323.308
• InChiKey: AIQPKXWIKLCGGM-UHFFFAOYSA-N

物化性质

• 熔点：
  >299 °C
• 沸点：
  683.5±50.0 °C(Predicted)
• 密度：
  1.553±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 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：
  110
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(2,6-dioxopiperidin-3-yl)-5-nitro-1H-benzo-[de]isoquinoline-1,3(2H)-dione 在 palladium 10% on activated carbon 、 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以88%的产率得到5-amino-2-(2,6-dioxopiperidin-3-yl)-1H-benzo[de]isoquinoline-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

• [EN] NEW CRBN MODULATORS<br/>[FR] NOUVEAUX MODULATEURS DU CRBN
  申请人：DANA FARBER CANCER INST INC

  公开号：WO2020006262A1

  公开（公告）日：2020-01-02

  Disclosed are degraders, pharmaceutical compositions containing them, and methods of making and using the degraders to treat diseases and disorders characterized by dysregulated or dysfunctional protein activity that can be targeted by cereblon.

  披露了降解剂，含有它们的药物组合物，以及制备和使用这些降解剂来治疗由可被 cereblon 靶向的蛋白质活性失调或功能失常所特征的疾病和紊乱的方法。
• NEW CRBN MODULATORS
  申请人：Dana Farber Cancer Institute, Inc.

  公开号：EP3813834A1

  公开（公告）日：2021-05-05
• 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.