2-氨基-2,3-二氢-1H-苯并[de]异喹啉-1,3-二酮 | 5690-46-0

• 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
• 中文名称: 2-氨基-2,3-二氢-1H-苯并[de]异喹啉-1,3-二酮
• 中文别名: 2-氨基苯并异喹啉-1,3-二酮
• 英文名称: 2-amino-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: N-amino-1,8-naphthalimide；N-aminonaphthalimide；N-Aminonaphthalimid；2-amino-benzo[de]isoquinolin-1,3-dione；2-aminobenzo[de]isoquinoline-1,3-dione
• CAS: 5690-46-0
• 化学式: C₁₂H₈N₂O₂
• mdl: MFCD00218903
• 分子量: 212.208
• InChiKey: HXJBFRDWVHNPAS-UHFFFAOYSA-N

物化性质

• 熔点：
  265 °C
• 沸点：
  463.0±28.0 °C(Predicted)
• 密度：
  1.470±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-氨基-2,3-二氢-1H-苯并[de]异喹啉-1,3-二酮 在 水 、 溶剂黄146 作用下， 生成 [2,2']bi[benzo[de]isoquinolinyl]-1,3,1',3'-tetraone
  参考文献：
  名称：

  Ostrogovich; Bena Median, Bull. Sect. Sci. Acad. Roum., 1942, vol. 25, p. 90,93,94

  摘要：

  DOI：
• 作为产物：
  描述：

  苊 在 sodium dichromate 、 一水合肼 作用下， 以 氯仿 为溶剂， 生成 2-氨基-2,3-二氢-1H-苯并[de]异喹啉-1,3-二酮
  参考文献：
  名称：

  A novel Schiff-base fluorescent probe based on 1,8-naphthyridine and naphthalimide for Al 3+

  摘要：

  A novel Schiff-base, 7-acetamino-4-methyl-1,8-naphthyridine-2-carbaldehyde-(1',8'-naphthalenedicarbonyl) hydrazone (HL) was designed, synthesized and evaluated as a fluorescent probe. The fluorescence properties of this probe towards various metal ions were investigated by UV-vis and fluorescence spectra in methanol. Test results indicated that the probe had high selectivity towards Al3+ over other commonly coexisting metal ions. Upon addition of Al3+, the fluorescence intensity at 414 nm increased significantly due to the inhibition of the PET process. The binding constant (Ma) of Al3+ binding to HL was calculated to be 5.64 x 10(4) M-1 from a Benesi-Hildebrand plot, and the detection limit(LOD) of HL for sensing Al3+ was calculated to be 0.13 mu M. The binding stoichiometry between HL and Al3+ was determined as 1:1 by the Job's plot. Furthermore, the probe was chemically reversible for Al3+ in methanol by the addition of Na(2)EDTA solution. (C) 2017 Published by Elsevier B.V.

  DOI：

  10.1016/j.ica.2017.05.032

文献信息

• Synthesis of 5-(4-(1H-phenanthro[9,10-d]imidazol-2-yl)benzylidene)thiazolidine-2,4-dione as promising DNA and serum albumin-binding agents and evaluation of antitumor activity
  作者：Iqubal Singh、Richa Rani、Vijay Luxami、Kamaldeep Paul

  DOI：10.1016/j.ejmech.2019.01.053

  日期：2019.3

  compound 8 with DNA have been investigated with absorption, emission and circular dichroism as well as thermal denaturation experiments which indicate intercalation with base pairs of human and calf thymus DNA. The molecular docking and site-selective binding studies also reveal the predominant intercalation of compound 8 in base pairs of DNA. The interaction between thiazolidine based phenanthrene 8 and

  合成了一系列在C2-位具有不同芳基的菲[9,10- d ]咪唑/恶唑和ena [1,2- d ]咪唑。这些化合物在体外评估了针对一组60种人类癌细胞系的抗肿瘤活性。化合物8对白血病，结肠癌，黑色素瘤，肾癌和乳腺癌细胞系的细胞毒性高于其他评估的细胞组，并且对正常细胞系Hek293的毒性低。化合物8的结合性能已经通过吸收，发射和圆二色性以及热变性实验研究了DNA与DNA的结合，该实验表明与人和小牛胸腺DNA的碱基对插入。分子对接和位点选择性结合研究还揭示了化合物8在DNA碱基对中的主要嵌入。还研究了基于噻唑烷的菲8与转运蛋白的血清白蛋白（HSA和BSA）之间的相互作用，该相互作用通过静态机制显示出荧光的猝灭。从范霍夫（Van't Hoff）关系获得的热力学参数表明了氢键/疏水相互作用对于结合现象的普遍性。
• Synthesis of Novel 2-Amino-benzo[de]isoquinolin-1,3-dione Derivatives
  作者：R. Al-Salahi、M. Marzouk

  DOI：10.14233/ajchem.2014.16848

  日期：——

  From a pioneer bioactive amino-benzoisoquinoline i.e. 2-amino-1H-benzo[de]isoquinolin-1,3-dione, a new series of Schiffs bases were prepared by the reaction of the active 2-amino group with a variety of aryl(hetero)aldehydes, isothiocyanides and acid anhydrides. The success of all reactions has been followed up by characterization of the synthesized target molecules through IR, Mass spectra and NMR analyses. The structural modifications were designed aiming at synthesis of valuable bioactive agents.

  从一个先驱生物活性氨基苯并异喹啉，即2-氨基-1H-苯并[de]异喹啉-1,3-二酮，通过其活性2-氨基基团与多种芳基（杂）醛、异硫氰酸酯和酸酐反应，制备了一系列新的席夫碱类化合物。通过对合成目标分子的IR、质谱和NMR分析，跟踪了所有反应的成功。结构修饰的设计旨在合成有价值的生物活性剂。
• <i>N</i> ‐Amino‐1,8‐Naphthalimide is a Regenerated Protecting Group for Selective Synthesis of Mono‐N‐Substituted Hydrazines and Hydrazides
  作者：Mesram Manoj Kumar、Parikibanda Venkataramana、Parikibanda Yadagiri Swamy、Yadaiah Chityala

  DOI：10.1002/chem.202102593

  日期：2021.12.15

  N-Amino-1,8-naphthalimide was used as a protecting group and a reagent to selective synthesis of various mono-N-substituted hydrazines and hydrazides. In all these reactions, the protecting reagent N-amino-1,8-naphthalimide was easily regenerated in good yields by the hydrazinolysis. All these transformations showed good functional-group tolerance and can be used for large scale C−N cross-coupling

  N-氨基-1,8-萘二甲酰亚胺用作保护基团和试剂，用于选择性合成各种单-N-取代的肼和酰肼。在所有这些反应中，保护试剂N-氨基-1,8-萘二甲酰亚胺很容易通过肼解以良好的产率再生。所有这些转化都显示出良好的官能团耐受性，可用于大规模的 CN 交叉偶联反应。
• 酰亚胺位或4-位取代的1，8-萘酰亚胺衍生物 作为PARP抑制剂的用途
  申请人：华侨大学

  公开号：CN103948595B

  公开（公告）日：2017-01-04

  本发明属于医药化学领域，公开了酰亚胺位或4‑位取代的1，8‑萘酰亚胺衍生物作为PARP抑制剂的用途，具体涉及通式（I）所示的1，8‑萘酰亚胺衍生物，通式（I）所示化合物药理或生理上可接受的盐，以及包含通式（I）所示化合物的药物组合物作为PARP抑制剂的用途。其中R1和R2具有所定义的含义。
• Carbonyl substituted pyrazoline compounds, their preparation and use as CB1 receptor modulators
  申请人：LABORATORIOS DEL DR. ESTEVE, S.A.

  公开号：EP1743888A1

  公开（公告）日：2007-01-17

  The present invention relates to substituted pyrazoline compounds, methods for their preparation, medicaments comprising these compounds as well as their use for the preparation of a medicament for the treatment of humans and animals.

  本发明涉及取代吡唑啉化合物，其制备方法，包含这些化合物的药物以及它们用于制备用于治疗人类和动物的药物的用途。