3-nitro-N-methyl-1,8-naphthalimide | 66266-37-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-nitro-N-methyl-1,8-naphthalimide
• 英文别名: 2-Methyl-5-nitro-benzo[de]isoquinoline-1,3-dione；2-methyl-5-nitrobenzo[de]isoquinoline-1,3-dione
• CAS: 66266-37-3
• 化学式: C₁₃H₈N₂O₄
• 分子量: 256.218
• InChiKey: RJZQKPFOBDQULU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-nitro-N-methyl-1,8-naphthalimide 在 甲酸 、 palladium on activated charcoal 作用下， 以 1,4-二氧六环 为溶剂， 以89 %的产率得到N-methyl-3-amino-1,8-naphthimide
  参考文献：
  名称：

  彩色3-氨基-1,8-萘二甲酰亚胺烷基取代荧光衍生物

  摘要：

  合成了四种氨基官能团取代度不同的 3-氨基-1,8-萘二甲酰亚胺衍生物的光学性质，并在 1:1 (v/v) 甲醇/水和甲醇。通过NMR、IR和HRMS对化合物进行了结构表征。观察到随着乙基取代度的增加，电荷转移吸收带向更长的波长移动。由于近场效应，还观察到发射带向更长的波长移动，发射强度随着乙基取代度的增加而降低。用 365 nm 紫外灯照射染料甲醇溶液和固态，显示出每种化合物不同的发射颜色。在甲醇中观察到比在混合甲醇水溶液中显着更大的斯托克斯位移。 B3LYP/TZVP 理论水平的量子化学计算提供了对优化基态几何结构、前沿分子轨道水平和溶质-溶剂动力学的深入了解，揭示了 3-氨基-1,8-萘二甲酰亚胺和甲醇之间的最强氢键S1激发态。这些染料在 MCF-7 癌细胞中作为荧光染料进行了测试，并观察到在各种细胞器中发出绿色发射。

  DOI：

  10.1016/j.dyepig.2024.112424
• 作为产物：
  描述：

  2-甲基-1H-苯并(去)异喹啉-1,3(2H)-二酮 在 aluminum(III) nitrate nonahydrate 、 乙酸酐 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 3-nitro-N-methyl-1,8-naphthalimide
  参考文献：
  名称：

  叠氮基-抗坏血酸反应的新策略：便捷的化学传感器及其在大蒜切片组织中的成像†

  摘要：

  抗坏血酸（AA）是许多水果和植物中至关重要的营养因子，AA含量异常与多种疾病密切相关。因此，开发用于监测生物系统中AA水平的便利方法非常重要。在这项工作中，我们设计并合成了三种化学传感器，用于通过叠氮-抗坏血酸反应的新策略快速启动AA的检测。的化学传感器是基于在不同的位点（探针叠氮基-1,8-萘二甲酰亚胺部分1，2，和3）。实验结果表明，探针2表现出对AA的高选择性，检测极限为74 nM。它的还原比带有3-取代叠氮化物基团的探针3的还原更容易。此外，探针2首次成功用于大蒜切片组织中AA的成像。

  DOI：

  10.1039/c8nj00589c

文献信息

• Effect of molecular structure and hydrogen bonding on the fluorescence of hydroxy-substituted naphthalimides
  作者：László Biczók、Pierre Valat、Ve´ronique Wintgens

  DOI：10.1039/a904520a

  日期：——

  Fluorescence properties of hydroxy-naphthalimides were studied in methylene chloride in the absence and the presence of hydrogen-bonding additives. The position of the HO-substituent only slightly affects the radiative rate, however, the triplet yield and the rate of the radiationless processes are considerably higher for the 3-hydroxy derivative. Addition of nitrogen-heterocyclic compounds leads not only to hydrogen-bonding in the ground state but also fluorescence quenching. The parallel change throughout the series of the hydrogen-bond acceptors between the proton affinity and the rate constants of dynamic quenching indicates that proton displacement plays a crucial role in the excited hydrogen-bonded complexes. Interaction of hydroxy-naphthalimides with pyridine and benzoxazole results in rapid radiationless deactivation from the singlet excited state, whereas intense emission as well as long fluorescence lifetime characterize imidazole and pyrazole complexes. The dual emission of the imidazole complexes observed in solvents of medium polarity is assigned to two conformers which differ in the extent of the proton shift along the hydrogen-bond.

  在二氯甲烷中，研究了羟基萘二甲酰亚胺在氢键添加剂存在和不存在情况下的荧光性质。HO-取代基的位置仅对辐射速率产生轻微影响，然而，3-羟基衍生物的三重态产率和无辐射过程的速率要高得多。氮杂环化合物的添加不仅会导致基态中的氢键，还会导致荧光淬灭。氢键受体在质子亲和力和动态淬灭速率常数之间的平行变化表明，质子位移在激发氢键复合物中起着至关重要的作用。羟基萘二甲酰亚胺与吡啶和苯并恶唑的相互作用会导致从单线态激发态快速无辐射失活，而咪唑和吡唑复合物则具有强烈的发射和较长的荧光寿命。在中等极性的溶剂中观察到的咪唑复合物的双重发射被归因于两种构象，它们在氢键沿线的质子位移程度方面有所不同。
• Efficient Sonochemical Synthesis of 3‐ and 4‐Electron Withdrawing Ring Substituted <i>N</i>‐Alkyl‐1,8‐naphthalimides from the Related Anhydrides
  作者：Eduardo Rezende Triboni、Pedro Berci Filho、Roberto Gomes de Souza Berlinck、Mario José Politi

  DOI：10.1081/scc-120037911

  日期：2004.12.31

  1,8-N-alkyl-naphthalimides substituted with electron withdrawing groups were readily prepared in high yields using ultrasound in aqueous media.
• 111. Derivatives of naphthalomethylimide
  作者：E. M. Francis、J. L. Simonsen

  DOI：10.1039/jr9350000496

  日期：——
• Naphthalimide Dosing by N-Acetyl Transferase Genotyping
  申请人：Brown Dennis M.

  公开号：US20110003742A1

  公开（公告）日：2011-01-06

  The present invention provides methods for dosing patients with naphthalimides, including amonafide, amonafide salts, and analogs thereof based on N-acetyl transferase genotyping. The invention also provides methods for dosing the amount of granulocyte colony stimulating factor (GCSF) used in combination with naphthalimide to prevent or modulate leukocytopenia.
• COMPOSITIONS AND METHODS TO IMPROVE THE THERAPEUTIC BENEFIT OF SUBOPTIMALLY ADMINISTERED CHEMICAL COMPOUNDS INCLUDING SUBSTITUTED NAPHTHALIMIDES SUCH AS AMONAFIDE FOR THE TREATMENT OF IMMUNOLOGICAL, METABOLIC, INFECTIOUS, AND BENIGN OR NEOPLASTIC HYPERPROLIFERATIVE DISEASE CONDITIONS
  申请人：BROWN Dennis M.

  公开号：US20160067241A1

  公开（公告）日：2016-03-10

  The present invention describes methods and compositions for improving the therapeutic efficacy of therapeutic agents previously limited by suboptimal therapeutic performance by either improving efficacy as monotherapy or reducing side effects. Such methods and compositions are particularly applicable to naphthalimides such as amonafide or analogs, derivatives, or prodrugs thereof.