6-((2-aminoethyl)amino)-2-(2-hydroxyethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione | 1279101-88-0

• 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
• 英文名称: 6-((2-aminoethyl)amino)-2-(2-hydroxyethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
• CAS: 1279101-88-0
• 化学式: C₁₆H₁₇N₃O₃
• 分子量: 299.329
• InChiKey: JBRASDYWJBAJLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  95.66
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-((2-aminoethyl)amino)-2-(2-hydroxyethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 在 吡啶 作用下， 以 丙酮 为溶剂， 反应 5.0h， 生成 2-[6-[2-(Benzoylcarbamothioylamino)ethylamino]-1,3-dioxobenzo[de]isoquinolin-2-yl]ethyl 2-methylprop-2-enoate
  参考文献：
  名称：

  Thermoresponsive Core Cross-Linked Micelles for Selective Ratiometric Fluorescent Detection of Hg²⁺ Ions

  摘要：

  We report on the fabrication of core cross-linked (CCL) micelles possessing thermoresponsive cores and their application as sensitive and selective ratiometric Hg2+ probes with thermo-tunable detection efficiency. Well-defined double hydrophilic block copolymer (DHBC) bearing naphthalimide-based Hg2+ -reactive moieties (NUMA, 4), PEO-b-P(NIPAM-co-NAS-co-NUMA), was synthesized via reversible addition - fragmentation chain transfer (RAFT) polymerization, where PEO, NIPAM, and NAS represent poly(ethylene oxide), N-isopropylacrylamide, and N-acryloxysuccinimide. At 25 degrees C, PEO-b-P(NIPAM-co-NAS-co-NUMA) unimers in aqueous solution can act as ratiometric Hg2+ probes with a detection limit of similar to 10.1 nM. After core cross-linking of the micellar nanoparticles formed at elevated temperatures, structurally stable CCL micelles with well-solvated PEO coronas and thermoresponsive cores embedded with Hg2+-reactive NUMA moieties were obtained. Upon Hg2+ addition, the aqueous dispersion of CCL micelles exhibit a colorimetric transition from yellowish to colorless and a fluorometric emission transition from green to bright blue. Moreover, Hg2+ detection limits of CCL micelles were considerably enhanced to 3.0 and 1.8 nM at 25 and 40 degrees C, when the thermoresponsive cores are at their swollen and collapsed state, respectively. The high selectivity of CCL micelles to Hg2+ over other common cations was also demonstrated. Furthermore, in vitro studies revealed that CCL micelles can effectively enter into living cells and sensitively respond to the presence of Hg2+ ions via the change of fluorescence emission color. This work represents the first example of DHBC-based CCL micelle acting as highly selective and sensitive ratiometric metal ion probes. The structural stability, water dispersibility, biocompatibility, and most importantly the thermo-tunable detection sensitivity of this novel type of CCL micelle-based sensing systems augur well for their future applications as multifunctional nanocarriers for drug delivery, sensing, imaging, and diagnosis.

  DOI：

  10.1021/la104911r
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以60%的产率得到6-((2-aminoethyl)amino)-2-(2-hydroxyethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  面向具有线粒体靶向的双SPECT /光学生物成像，99mTc（i）放射性标记的1,8-萘二甲酰亚胺共轭物。

  摘要：

  合成并表征了一系列六个不同的1,8-萘二甲酰亚胺共轭二聚烯丙基胺配体（L1-6）。所述配体在萘甲酰亚胺荧光团和二甘醇胺螯合剂之间具有一系列不同的接头单元，这可以调节整体的亲脂性。合成了一系列相应的Re（i）配合物，形式为fac- [Re（CO）3（L1-6）] BF4。配体和Re（i）配合物的吸收和发光特性主要由取代的荧光团的分子内电荷转移特性决定（通常约425 nm的吸收和约520 nm的发射）。光物理评估表明，某些变体是中等亮度的。使用fac- [99mTc（CO）3（H2O）3] +成功进行了使用水溶性配体变异体（L5）的放射性标记实验，并对其进行了优化。共聚焦荧光显微镜显示，fac- [Re（CO）3（L5）] +定位于MCF-7细胞的线粒体。在幼稚小鼠上进行的SPECT / CT成像实验表明，fac- [99mTc（CO）3（L5）] +在体内具有相对较高的稳定性，但未显示任何心

  DOI：

  10.1039/c9dt04024b

文献信息

• Engineered Artesunate-Naphthalimide Hybrid Dual Drug for Synergistic Multimodal Therapy against Experimental Murine Lymphoma
  作者：Debapriya RoyMahapatra、Ranjeet Singh、Ugir Hossain Sk、Partha Pratim Manna

  DOI：10.1021/acs.molpharmaceut.3c00632

  日期：2024.3.4

  overall increase the prognosis rate. A new series of substituted naphthalimide moieties conjugated via ester and amide linkages with artesunate were designed, synthesized, and characterized. In addition to the conjugates, to further achieve a theranostic molecule, FITC was incorporated via a multistep synthesis process. DNA binding studies of these selected derivatives by ultraviolet–visible (UV–vis), fluorescence

  淋巴瘤可以用化疗方案有效治疗，但化疗方案会因耐药性增加而产生不良副作用，因此迫切需要替代的小分子抑制剂来克服淋巴瘤治疗中出现的耐药性并总体提高预后率。设计、合成并表征了一系列通过酯键和酰胺键与青蒿琥酯缀合的新的取代萘酰亚胺部分。除了缀合物之外，为了进一步实现治疗诊断分子，还通过多步合成过程掺入了 FITC。通过紫外可见 (UV-vis)、荧光光谱、嵌入染料（EtBr、吖啶橙）-DNA 竞争性测定和小沟结合染料 Hoechst 33342-DNA 竞争性测定对这些选定衍生物进行 DNA 结合研究表明，合成的新分子由于其萘甲酰亚胺部分而插入 DNA 的两条链之间，而其对应物青蒿酯与 DNA 的小沟结合。萘甲酰亚胺-青蒿琥酯缀合物抑制淋巴瘤的生长并诱导细胞凋亡，包括快速掺入和细胞活力降低。该改造药物对 BALB/c 小鼠体内产生的实体 DL 肿瘤具有显着的杀瘤作用，且呈剂量依赖性。与未经治疗的同