9-fluoropyrido[2',3':4,5]pyrimido[1,2-α]indole-5,11-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 9-fluoropyrido[2',3':4,5]pyrimido[1,2-α]indole-5,11-dione
• 英文别名: 4-aza-8-fluorotryptanthrin；2-Fluoro-4b,9,10-triaza-benzo[b]fluorene-5,11-dione；14-fluoro-2,4,10-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1,3(8),4,6,11(16),12,14-heptaene-9,17-dione
• 化学式: C₁₄H₆FN₃O₂
• 分子量: 267.219
• InChiKey: AKHMUNBSKUODAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基烟酸 、 5-氟靛红 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N-甲基吗啉 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 9-fluoropyrido[2',3':4,5]pyrimido[1,2-α]indole-5,11-dione
  参考文献：
  名称：

  作为新型抗植物病原体细菌剂的有效杀菌剂的发现和作用机制

  摘要：

  色胺菊酯及其衍生物是天然生物碱，具有广泛的生物活性。本研究采用抗植物病原体的缩合环化反应制备了4个系列的含4-aza/3-aza/2-aza/1-aza色胺菊酯的氮杂色胺酮衍生物，开发了一种新型天然产物型细菌农药。化合物4Aza-8对轴突黄单胞菌pv的致病菌表现出显着的生长抑制作用。柑橘( Xac ),米黄单胞菌pv。Oryzae ( Xoo ) 和Pseudomonas syringae pv。猕猴桃( Psa) 最终校正后的 EC 50值分别为 0.312、1.91 和 18.0 μg/mL，大大优于色胺酮 (Tryp)。此外，4Aza-8在体内对柑橘溃疡病也显示出有效的治疗和保护活性。对Xac 的进一步机制研究表明化合物4Aza-8能够影响Xac的生长曲线和生物膜的形成，导致细菌形态严重收缩，增加活性氧水平，并诱导细菌细胞凋亡。对差异蛋白谱的定量分析发现，主要差异主要集中在细菌分泌系

  DOI：

  10.1021/acs.jafc.3c01120

文献信息

• Antimalarial and antiproliferative pharmacophore models, novel tryptanthrin compounds having increased solubility, and methods of making and using thereof
  申请人：——

  公开号：US20040033934A1

  公开（公告）日：2004-02-19

  Disclosed herein is a pharmacophore model for antimalarial activity and methods of making and using thereof. The pharmacophore comprises two hydrogen bond acceptor (lipid) functions and two hydrophobic (aromatic) functions. The pharmacophore model was made using a test set of tryptanthrin compounds which exhibit antimalarial activity. Also disclosed are tryptanthrin compounds having greater solubility and bioactivity as compared to prior art tryptanthrin compounds and methods of making and using thereof. Also disclosed are methods of treating malaria in a subject.

  本文揭示了一种抗疟药物活性的药效团模型及其制备和使用方法。该药效团包括两个氢键受体（脂肪）功能和两个疏水（芳香）功能。该药效团模型是使用一组具有抗疟活性的色胺类化合物试验集制备的。还揭示了具有比先前技术的色胺类化合物更高溶解度和生物活性的色胺类化合物及其制备和使用方法。还揭示了治疗受体内疟疾的方法。
• Use of tryptanthrin compounds for immune potentiation
  申请人：Chiron Corporation

  公开号：US20040241192A1

  公开（公告）日：2004-12-02

  The invention provides immunostimulatory compositions and methods of administration thereof. Also provided are methods of administering a tryptanthrin compound in an effective amount to enhance the immune response of a subject to an antigen. Also provided are methods of administering an effective amount of a tryptanthrin to stimulate the immune response in a subject for the treatment of cancer. Further provided are methods of administering a tryptanthrin compounds as an immunotherapeutic in the treatment of infectious diseases.

  该发明提供了免疫刺激性组合物及其给药方法。还提供了一种给予色胺酸酸衍生物有效量的方法，以增强受体对抗原的免疫反应。还提供了一种给予有效量色胺酸酸衍生物的方法，以刺激受体的免疫反应，用于治疗癌症。此外，还提供了一种给予色胺酸酸衍生物作为免疫治疗剂治疗传染病的方法。
• USE OF TRYPTANTHRIN COMPOUNDS FOR IMMUNE POTENTIATION
  申请人：VALIANTE Nicholas M.

  公开号：US20120244182A1

  公开（公告）日：2012-09-27

  The invention provides immunostimulatory compositions and methods of administration thereof. Also provided are methods of administering a tryptanthrin compound in an effective amount to enhance the immune response of a subject to an antigen. Also provided are methods of administering an effective amount of a tryptanthrin to stimulate the immune response in a subject for the treatment of cancer. Further provided are methods of administering a tryptanthrin compounds as an immunotherapeutic in the treatment of infectious diseases.

  本发明提供了免疫刺激组合物及其给药方法。还提供了一种给予吲哚丹宁化合物有效量的方法，以增强受体对抗原的免疫反应。还提供了一种给予有效量的吲哚丹宁化合物的方法，以刺激受体对癌症的免疫反应。此外，还提供了将吲哚丹宁化合物作为免疫治疗剂治疗传染病的方法。
• NITROGEN HETEROCYCLIC TRYPTAMINE KETONE DERIVATIVE AND APPLICATION AS IDO1 AND/OR TDO INHIBITOR
  申请人：Peking University

  公开号：EP3421472A1

  公开（公告）日：2019-01-02

  This invention discloses the use of aza-tryptanthrin derivatives as an IDO1 and/or TDO inhibitors, and the derivatives are represented by the general Formula (I). The compounds represented by the Formula (I) have inhibitory effects on indoleamine-2,3-dioxygenase 1 (IDO1) and/or tryptophan-2,3-dioxygenase (TDO), and can be used for treating diseases having the pathological features of IDO1 and/or TDO-mediated tryptophan metabolism, including but not limited to tumors, autoimmune disease, infectious diseases, Alzheimer's disease, depression, anxiety.

  本发明公开了氮杂色蒽衍生物作为IDO1和/或TDO抑制剂的用途，其衍生物由通式（I）表示。由式（I）表示的化合物对吲哚胺-2,3-二氧合酶1（IDO1）和/或色氨酸-2,3-二氧合酶（TDO）具有抑制作用，可用于治疗具有IDO1和/或TDO介导的色氨酸代谢病理特征的疾病，包括但不限于肿瘤、自身免疫性疾病、传染性疾病、阿尔茨海默病、抑郁症、焦虑症等。
• Use of aza-tryptanthrin derivatives as inhibitors of IDO1 and/or TDO
  申请人：Peking University

  公开号：US10669273B2

  公开（公告）日：2020-06-02

  This invention discloses the use of aza-tryptanthrin derivatives as an IDO1 and/or TDO inhibitors, and the derivatives are represented by the general Formula (I). The compounds represented by the Formula (I) have inhibitory effects on indoleamine-2,3-dioxygenase 1 (IDO1) and/or tryptophan-2,3-dioxygenase (TDO), and can be used for treating diseases having the pathological features of IDO1 and/or TDO-mediated tryptophan metabolism, including but not limited to tumors, autoimmune disease, infectious diseases, Alzheimer's disease, depression, anxiety.

  本发明公开了氮杂色蒽衍生物作为IDO1和/或TDO抑制剂的用途，其衍生物由通式（I）表示。由式（I）表示的化合物对吲哚胺-2,3-二氧合酶1（IDO1）和/或色氨酸-2,3-二氧合酶（TDO）具有抑制作用，可用于治疗具有IDO1和/或TDO介导的色氨酸代谢病理特征的疾病，包括但不限于肿瘤、自身免疫性疾病、传染性疾病、阿尔茨海默病、抑郁症、焦虑症等。