6-(6-amino-1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-hexanoic acid | 172227-58-6

• 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-(6-amino-1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-hexanoic acid
• 英文别名: 6-(6-amino-1,3-dioxobenzo[de]isoquinolin-2-yl)hexanoic acid
• CAS: 172227-58-6
• 化学式: C₁₈H₁₈N₂O₄
• 分子量: 326.352
• InChiKey: SSNOFPOASKJQGN-UHFFFAOYSA-N

物化性质

• 沸点：
  611.4±45.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(6-amino-1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-hexanoic acid 在 吡啶 、 TEA 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 26.5h， 生成 6-[6-isobutyrylamino-1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl]-hexanoic acid p-nitrophenyl ester
  参考文献：
  名称：

  Synthesis and Biophysical Studies on Fluorescently Labeled Oligodeoxyribonucleotides

  摘要：

  Two highly fluorescent compounds, viz. 6-(6-isobutyrylamino-1,3-dioxo-1 H,3H-benzo[de]isoquinolin-2-yl)-hexanoic acid and 6-(6-dimethylamino-1,3-dioxo-1 H,3H-benzo[de]isoqu-inolin-2-yl)-hexanoic acid have been synthesized, characterized, and attached to 12-mer oligodeoxyribonucleotides at their 5'-end using suitable linker molecule. These labeled oligodeoxyribonucleotides have shown appreciable fluorescence even at 0.0019 microM concentrations. Thermal denaturation studies have shown comparatively higher Tm values when oligodeoxyribonucleotides are labeled. These labeled oligodeoxyribonucleotides have been purified on RP-HPLC utilizing their hydrophobicity and on polyacrylamide gel because of their easy detection due to fluorescence.

  DOI：

  10.1080/15257770701426294
• 作为产物：
  描述：

  4-nitro-1,8-naphthalimide-N-caproic acid 在 盐酸 、 tin 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以80%的产率得到6-(6-amino-1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-hexanoic acid
  参考文献：
  名称：

  Dubey, Krishna K.; Singh, Ramendra K.; Misra, Krishna, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 10, p. 876 - 878

  摘要：

  DOI：

文献信息

• 一种四价铂萘酰亚胺配合物、其制备方法及应 用
  申请人：河南大学

  公开号：CN111393483B

  公开（公告）日：2021-09-10

  本发明属于药物化学技术领域，具体涉及一种四价铂萘酰亚胺配合物、其制备方法及应用。本发明所述四价铂萘酰亚胺配合物具有良好的抗肿瘤活性，其抗肿瘤活性比顺铂、奥沙利铂均较好，且与顺铂、卡铂、奥沙利铂等二价铂类相比较稳定性较好。本发明通过利用萘酰亚胺修饰的四价铂对肿瘤细胞具有较好的靶向性，提高了对肿瘤细胞的高选择性，与经典的二价铂药物不同，本发明所述配合物通过靶向肿瘤高多胺微环境调控亚细胞器及细胞核功能逆转耐药，同时解除肿瘤周围T细胞免疫抑制。本发明所述配合物还解决了以往二价铂类抗肿瘤药物的溶解性差、临床配伍较繁琐、化疗药物临床应用中病人免疫力差等问题，脂溶性以及水溶性均较好。
• Synthesis and Photophysical Studies on Naphthalimide Derived Fluorophores as Markers in Drug Delivery
  作者：Nidhi Singh、Ritika Srivastava、Anuradha Singh、Ramendra K. Singh

  DOI：10.1007/s10895-016-1835-y

  日期：2016.7

  Derivatives of 4-amino-1,8-naphthalimide containing a free alkyl chain bearing carboxyl group as linker and different substituents at 4-amino function have been synthesized, characterized and studied for their photophysical properties. Steady state fluorescence studies showed quantum yield varied from 0.45 to 0.65 with Stokes shift in the range of 5824–8558 cm−1. Spectroscopic and physicochemical parameters, like electronic absorption, emission, and extinction coefficient were investigated in order to explore the analytical potential of compounds. Solvatochromic studies demonstrated that all compounds were sensitive towards the polarity of different solvents showing the highest degree of fluorescence in acetonitrile. In addition, the compounds in the presence of ions, viz. Na+, K+ and Mg2+ at concentration of 0.1–2 equivalents, showed a decreasing trend in fluorescence with increasing ionic concentration. TCSPC set – up was used to measure the fluorescence lifetime of compounds, which was found to be bi-exponential with longer and shorter component at their respective amplitudes. The average lifetime of compounds was observed to be 5.76–9.96 ns indicating the possibility of their greater utilization in research and diagnosis.

  研究人员合成了 4-氨基-1,8-萘二甲酰亚胺的衍生物，并对其光物理性质进行了表征和研究，这些衍生物含有一个以羧基为连接基的游离烷基链和 4-氨基官能团上的不同取代基。稳态荧光研究表明，量子产率在 0.45 到 0.65 之间，斯托克斯位移范围为 5824-8558&nbSP;cm-1。为了探索化合物的分析潜力，对其光谱和理化参数（如电子吸收、发射和消光系数）进行了研究。溶解变色研究表明，所有化合物对不同溶剂的极性都很敏感，在乙腈中的荧光程度最高。此外，在离子（即 Na+、K+ 和 Mg2+，浓度为 0.1-2 当量）存在的情况下，化合物的荧光随着离子浓度的增加呈下降趋势。TCSPC 装置用于测量化合物的荧光寿命，结果发现它是双指数型的，在各自的振幅上有较长和较短的分量。化合物的平均寿命为 5.76-9.96ns，这表明它们有可能在研究和诊断中得到更广泛的应用。
• Novel Fluorophores for Labeling of Nucleosides and Oligonucleotides
  作者：Shipra Singh、Ramendra K. Singh

  DOI：10.1080/15257770701547222

  日期：2007.11.26

  Five novel fluorophores have been synthesized and their comparative fluorescence has been studied in different organic solvents and aqueous solutions of inorganic ions. Out of these, two highly sensitive fluorophores have been used to label phosphoramidites and oligodeoxyribonucleotides. The fluorescently labelled amidites and oligodeoxyribonucleotides showed good fluorescence signals.