8-aminoindolo[2,1-b]quinazoline-6,12-dione | 483349-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 8-aminoindolo[2,1-b]quinazoline-6,12-dione
• CAS: 483349-71-9
• 化学式: C₁₅H₉N₃O₂
• 分子量: 263.255
• InChiKey: GXWUJSVZVDFGGN-UHFFFAOYSA-N

物化性质

• 沸点：
  561.4±52.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

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：
  75.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-aminoindolo[2,1-b]quinazoline-6,12-dione 在 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成
  参考文献：
  名称：

  Zn(II) 与混合色氨酸衍生物和姜黄素螯合配体的配合物作为新的有前途的抗癌剂

  摘要：

  在本研究中，两种新型姜黄素（H-Cur）-色氨酸金属化合物——[Zn(TA)Cl 2 ]，即Zn (TA)和 [Zn(TA)(Cur)]Cl，即Zn (TAC ) — 使用 5-(bis-pyridin-2-ylmethyl-amino)-pentanoic acid (6,12-dioxo-6,12-dihydro-indolo[2,1- b ]quinazolin-8-yl)合成和研究-酰胺（TA）和H-Cur分别作为靶向和高活性抗癌化疗部分。然后将它们与二-(2-吡啶甲基)胺( PA )Zn( II )络合物[Zn(PA)Cl 2 ]，即Zn (PA)进行比较。与Zn(PA)相比和顺铂， Zn(TA)和Zn(TAC)的 IC 50值表明该化合物对 A549/DDP 癌细胞具有较高的细胞毒性，表明 H-Cur-色氨酸 Zn( II ) 化合物具有用作抗癌药物。我们建议使用具有核靶向和 DNA

  DOI：

  10.1039/d1dt04095b
• 作为产物：
  描述：

  色胺酮 在 盐酸 、 tin(II) chloride dihdyrate 、 硫酸 、 硝酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 8-aminoindolo[2,1-b]quinazoline-6,12-dione
  参考文献：
  名称：

  具有苯磺酰胺取代基的新型色胺酮衍生物：设计、合成和抗炎评价

  摘要：

  在此，设计并合成了两个系列的带有苯磺酰胺取代基的色胺酮衍生物，以发现新型抗炎剂。通过评估所有衍生物对脂多糖（LPS）诱导的RAW264.7细胞中一氧化氮（NO）产生的抑制作用来筛选所有衍生物的抗炎活性。其中，化合物8j表现出最佳的NO抑制活性（IC 50 = 1.25 ± 0.21 μM），且无明显毒性。进一步评估表明， 8j还可以显着降低促炎细胞因子白细胞介素-1β（IL-1β，IC 50 = 8.48 ± 0.23 μM）和肿瘤坏死因子-α（TNF-α，IC 50 = 11.53 ± 0.35 μM）的水平) 并下调 LPS 诱导的 iNOS 和 COX-2 表达。 8j的反向对接表明 p38α 作为分子靶标，它是控制促炎介质转录的 p38 MAPK 信号通路中众所周知的关键角色。细胞热位移测定表明， 8j有效稳定 LPS 处理的 RAW264.7 细胞中的 p38α。 Western

  DOI：

  10.1016/j.ejmech.2022.114956

文献信息

• 色胺酮衍生物及其制备和在防治植物病毒病菌病中的应用
  申请人：南开大学

  公开号：CN113024561B

  公开（公告）日：2022-09-13

  本发明涉及色胺酮类衍生物I‑1～I‑7及其制备方法和在防治植物病毒病菌病中的应用。本发明的色胺酮类衍生物I‑1～I‑7显示出抗植物病毒活性，能很好地抑制烟草花叶病毒，同时该类化合物也表现出广谱的抗植物病菌活性，且对苹果轮纹病菌的抑制活性突出。
• 基于二甲基吡啶胺-锌的高抗癌活性配合物及其衍生物和制备方法
  申请人：广东石油化工学院

  公开号：CN114057778B

  公开（公告）日：2023-05-12

  本发明公开了一种基于二甲基吡啶胺‑锌的高抗癌活性配合物及其衍生物和制备方法，属于医药技术领域。它包括将配体和ZnY2混合并溶于极性溶剂中进行反应，反应得到的固体为所述配合物，所述Y为卤素，所述配体包括配体A。本发明的配合物能够对A549/DDP等癌细胞进行选择性地治疗，其IC50值可达0.14μM±0.03μM，其体外抗肿瘤活性远远大于各配体和经典的金属基抗癌药物顺铂，且对正常HL‑7702细胞的毒性低(IC50>100μM)，既解决了现有的顺铂耐药性癌细胞难以被顺铂类药物治疗的问题，同时也几乎不会对人体造成伤害，具有极大的医疗应用前景。
• 一种8-胺基苯磺酰胺取代的色胺酮类衍生物及其制备和应用
  申请人：安徽瀚海博兴生物技术有限公司

  公开号：CN114874220B

  公开（公告）日：2023-04-21

  本发明涉及一种8‑胺基苯磺酰胺取代的色胺酮类衍生物及其制备和应用。该化合物结构式如式A所示：其中，R为4‑溴、4‑氟、3‑氟、2‑氟、4‑异丙基、4‑叔丁基、氢、2‑(三氟甲氧基)、4‑(三氟甲氧基)、3,4‑二(三氟甲氧基)、2,4‑二(三氟甲氧基)、4‑乙酰氨基中的任意一种。该化合物可选择性的抑制乙酰胆碱酯酶的活性，并具有选择性螯合金属离子、抗Aβ1‑42自聚集等能力，有潜力发展成为治疗阿尔兹海默症的药物。
• Design, Synthesis, and Structure–Activity Relationship Studies of Tryptanthrins As Antitubercular Agents
  作者：Jae-Min Hwang、Taegwon Oh、Takushi Kaneko、Anna M. Upton、Scott G. Franzblau、Zhenkun Ma、Sang-Nae Cho、Pilho Kim

  DOI：10.1021/np3007167

  日期：2013.3.22

  The natural product tryptanthrin (la) represents a potential lead for new tuberculosis (TB) drugs since tryptanthrin and its synthetic analogues possess potent in vitro activity against Mycobacterium tuberculosis (Mtb). However, in spite of their in vitro activity, none of these agents have been shown to be efficacious in vivo against animal models of TB. Described herein are syntheses of new tryptanthrin analogues together with a systematic investigation of their in vitro antitubercular activity and ADME properties followed by pharmacokinetic characterization in rodents for the most promising compounds. Those with the best potency and oral bioavailability were progressed to evaluations of efficacy against acute murine TB. The work aimed to prove the concept that this compound class can limit growth of Mtb during infection as well as to establish the SAR for in vitro activity against Mtb and the range of in vitro ADME parameters for this class of natural products. Novel C-11-deoxy (5b) and A-ring-saturated (6) tryptanthrin analogues were discovered that maintained activity against Mtb and showed improved solubility compared to tryptanthrin as well as evidence of oral bioavailability in rodents. However, neither 5b nor 6 demonstrated efficacy against acute murine TB following administration at doses up to 400 mg/kg daily for 4 weeks. Although 5b and 6 failed to inhibit replication or kill Mtb in vivo, they illuminate a path to new structural variations of the tryptanthrin scaffold that may maximize the potential of this class of compounds against TB.
• Discovery of Tryptanthrins as Novel Antiviral and Anti-Phytopathogenic-Fungus Agents
  作者：Yanan Hao、Jincheng Guo、Ziwen Wang、Yuxiu Liu、Yongqiang Li、Dejun Ma、Qingmin Wang

  DOI：10.1021/acs.jafc.0c02101

  日期：2020.5.20

  Plant diseases seriously affect the yield and quality of crops and are difficult to control. Tryptanthrin and its derivatives (tryptanthrins) were synthesized and evaluated for their antiviral activities and fungicidal activities. We found that tryptanthrins have good antiviral activities against tobacco mosaic virus (TMV) for the first time. Most of the tryptanthrins showed higher anti-TMV activities than that of ribavirin (inhibitory rates of 40, 37, and 38% at 500 mu g/mL for inactivation, curative, and protection activities in vivo, respectively). Compound 3n (inhibitory rates of 52, 49, and 54% at 500 mu g/mL for inactivation, curative, and protection activities in vivo, respectively) and compound 14 (inhibitory rates of 51, 48, and 53% at 500 mu g/mL for inactivation, curative, and protection activities in vivo, respectively) emerged as new antiviral lead compounds with excellent antiviral activities. Compound 16 was selected for further antiviral mechanism research, which revealed that compound 16 could inhibit virus assembly by decomposing 20S coat protein (CP) disk. Molecular docking results showed that compounds 3n and 14, which have higher antiviral activities in vivo than that of compound 16, do show stronger interaction with TMV CP. Further fungicidal activity tests showed that tryptanthrins displayed broad-spectrum fungicidal activities, especially for compound 16. These compounds showed good selectivity to Physalospora piricola. In the current study, a small molecular library of tryptanthrin was constructed and the bioactivity spectrum of these compounds was broadened, which lays a foundation for their application in plant protection.