6-bromo-2-octyl-1H-benzo[de]isoquinoline-1,3(2H)-dione

• 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-bromo-2-octyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: N-octyl-4-bromo-1,8-naphthalimide；4-bromo-N-octyl-1,8-naphthalimide；6-bromo-2-octylbenzo[de]isoquinoline-1,3-dione
• 化学式: C₂₀H₂₂BrNO₂
• 分子量: 388.304
• InChiKey: YRFMRQKBCBLXMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-bromo-2-octyl-1H-benzo[de]isoquinoline-1,3(2H)-dione 在 四丁基溴化铵 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 氯仿 、 乙二醇甲醚 为溶剂， 反应 72.0h， 生成 6-((2-(1,4,8,11-tetraazacyclotetradecan-1-yl)ethyl)amino)-2-octyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Antiproliferative and apoptosis-inducing activities of novel naphthalimide–cyclam conjugates through dual topoisomerase (topo) I/II inhibition

  摘要：

  A novel series of naphthalimide-cyclam conjugates were designed and synthesized. Among them, compounds 4c, 4d, 8c and 8d which bearing long lipophilic alkyl chains, displayed comparable or more potent cytotoxic activities against human tumor cell lines than amonafide. Furthermore, the four compounds were proved to possess strong inhibition against both topoisomerase I and II. The representative compound 8c exhibited moderate DNA intercalation activity. Molecular modeling studies identified the possible interaction of compound 8c with the molecular target by forming topoisomerase/DNA/drug ternary complex. Finally, derivatives with long lipophilic alkyl chains could efficiently induce apoptosis. (C) 2015 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2015.07.011
• 作为产物：
  描述：

  1,8-萘二甲酸酐 在 溴 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 6-bromo-2-octyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  吲哚离子官能化的萘二甲酰亚胺化学计量仪在水性介质中检测氰化物

  摘要：

  摘要合成并表征了基于萘二甲酰亚胺平台的吲哚离子官能化比色法和荧光化学计量仪（L）。这样可以选择性地检测水性介质中的氰化物（CN-），且检测限较低（约0.5μM），这比WHO设定的1.9μM值低约四倍。在40％的乙腈水溶液中进行了UV-vis和PL研究，该介质在可见光区域显示出显着变化，从而可以用肉眼比色法检测CN。质谱和1 H NMR光谱用于表征相应的氰化物加合物，其在建立传感机制期间也得到了时变密度泛函理论（TD-DFT）的证实。

  DOI：

  10.1016/j.ica.2018.08.040

文献信息

• Electron transfer dynamics and excited state branching in a charge-transfer platinum(<scp>ii</scp>) donor–bridge-acceptor assembly
  作者：Paul A. Scattergood、Milan Delor、Igor V. Sazanovich、Oleg V. Bouganov、Sergei A. Tikhomirov、Alexander S. Stasheuski、Anthony W. Parker、Gregory M. Greetham、Michael Towrie、E. Stephen Davies、Anthony J. H. M. Meijer、Julia A. Weinstein

  DOI：10.1039/c4dt01682c

  日期：——

  A linear asymmetric Pt(II) trans-acetylide donor–bridge-acceptor triad designed for efficient charge separation, NAPPt(PBu3)2Ph–CH2–PTZ (1), containing strong electron acceptor and donor groups, 4-ethynyl-N-octyl-1,8-naphthalimide (NAP) and phenothiazine (PTZ) respectively, has been synthesised and its photoinduced charge transfer processes characterised in detail. Excitation with 400 nm, ∼50 fs laser pulse initially populates a charge transfer manifold stemming from electron transfer from the Pt-acetylide centre to the NAP acceptor and triggers a cascade of charge and energy transfer events. A combination of ultrafast time-resolved infrared (TRIR) and transient absorption (TA) spectroscopies, supported by UV-Vis/IR spectroelectrochemistry, emission spectroscopy and DFT calculations reveals a self-consistent photophysical picture of the excited state evolution from femto- to milliseconds. The characteristic features of the NAP-anion and PTZ-cation are clearly observed in both the TRIR and TA spectra, confirming the occurrence of electron transfer and allowing the rate constants of individual ET-steps to be obtained. Intriguingly, 1 has three separate ultrafast electron transfer pathways from a non-thermalised charge transfer manifold directly observed by TRIR on timescales ranging from 0.2 to 14 ps: charge recombination to form either the intraligand triplet 3NAP with 57% yield, or the ground state, and forward electron transfer to form the full charge-separated state 3CSS (3[PTZ+–NAP−]) with 10% yield as determined by target analysis. The 3CSS decays by charge-recombination to the ground state with ∼1 ns lifetime. The lowest excited state is 3NAP, which possesses a long lifetime of 190 μs and efficiently sensitises singlet oxygen. Overall, molecular donor–bridge-acceptor triad 1 demonstrates excited state branching over 3 different pathways, including formation of a long-distant (18 Å) full charge-separated excited state from a directly observed vibrationally hot precursor state.

  设计了一种用于高效电荷分离的线性非对称Pt(II)反式乙炔供体-桥-受体三联体,含强电子受体和供体基团的NAPPt(PBu3)2Ph-CH2-PTZ(1)(4-乙炔基-N-辛基-1,8-萘酰亚胺(NAP)和吩噻嗪(PTZ)),已合成并详细表征了其光诱导电荷转移过程。用400nm、~50fs激光脉冲激发,首先在Pt-乙炔中心和NAP受体间发生电子转移,形成电荷转移系,并触发一系列级联的电荷和能量转移事件。在UV-Vis/IR光谱电化学、发射光谱和DFT计算的支持下,结合超快时间分辨红外(TRIR)光谱和瞬态吸收(TA)光谱,揭示了从飞秒到毫秒量级自洽的光物理图像,即激发态的演变过程。在TRIR和TA光谱中清楚地观察到NAP阴离子和PTZ阳离子的特征,证实了电子转移的发生,并得到了单个电子转移步骤的速率常数。有趣的是,1在0.2~14ps的时间尺度上,通过TRIR直接观察到非热化电荷转移系的三个独立的超快电子转移通道:电荷复合,分别形成萘酰亚胺三重激发态3NAP,得率57%,或形成基态;以及正向电荷转移,形成完全电荷分离态3CSS,得率10%,根据目标分析得出。3CSS通过电荷复合回到基态,寿命约为1ns。最低激发态为3NAP,具有190μs的长寿命,能高效地敏化单线态氧。总体而言,分子供体-桥-受体三联体1展示了在三种不同的途径上的激发态分支,包括从直接观察到的振动性热的先驱态形成长距离(18Å)的完全电荷分离激发态。
• 萘酰亚胺类衍生物及其制备方法和应用
  申请人：西南大学

  公开号：CN107501178B

  公开（公告）日：2020-07-28

  本发明公开了一类具有通式I～IV结构的萘酰亚胺类衍生物及其可药用盐，这些化合物对革兰阳性菌、革兰阴性菌和真菌都有一定的抑制活性，可用于制备抗细菌和/或抗真菌药物。其制备原料商业化程度高、便宜易得，制备路线短、方法简便。
• A novel ternary memory property achieved through rational introduction of end-capping naphthalimide acceptors
  作者：Qijian Zhang、Jinghui He、Hua Li、Najun Li、Qingfeng Xu、Dongyun Chen、Jianmei Lu

  DOI：10.1039/c7tc01796k

  日期：——

  Small molecule-based multilevel rewritable memory devices have gained attention because they possess super-high storage density, can sustain the stored data without power supply and erase/rewrite electrically; however, formation of these memory devices is extremely hard to achieve.

  基于小分子的多级可重写存储器设备受到关注，因为它们具有超高的存储密度，可以在没有电源供应的情况下维持存储的数据，并可以通过电气方式进行擦除/重写；然而，这些存储器设备的形成非常难以实现。
• Towards Highly-Efficient Phototriggered Data Storage by Utilizing a Diketopyrrolopyrrole-Based Photoelectronic Small Molecule
  作者：Yang Li、Hua Li、Jinghui He、Qingfeng Xu、Najun Li、Dongyun Chen、Jianmei Lu

  DOI：10.1002/asia.201600692

  日期：2016.7.20

  A cooperative photoelectrical strategy is proposed for effectively modulating the performance of a multilevel data‐storage device. By taking advantage of organic photoelectronic molecules as storage media, the fabricated device exhibited enhanced working parameters under the action of both optical and electrical inputs. In cooperation with UV light, the operating voltages of the memory device were

  为了有效地调节多级数据存储设备的性能，提出了一种协同光电策略。通过利用有机光电子分子作为存储介质，所制造的装置在光和电输入的作用下表现出增强的工作参数。与紫外线合作，降低了存储设备的工作电压，这有利于降低能耗。此外，开/关电流比更可调，并有助于高分辨率多层存储。与以前专注于调整存储介质的方法相比，本研究提供了一种通过多个物理通道优化有机设备的简便方法。更重要的是，
• Activation of Cell-Penetrating Peptides with Ionpair−π Interactions and Fluorophiles
  作者：Nicolas Chuard、Kaori Fujisawa、Paola Morelli、Jacques Saarbach、Nicolas Winssinger、Pierangelo Metrangolo、Giuseppe Resnati、Naomi Sakai、Stefan Matile

  DOI：10.1021/jacs.6b06253

  日期：2016.9.7

  In this report, we elaborate on two new concepts to activate arginine-rich cell-penetrating peptides (CPPs). Early on, we have argued that repulsion-driven ion-pairing interactions with anionic lipids account for their ability to move across hydrophobic cell membranes and that hydrophobic anions such as pyrenebutyrate can accelerate this process to kinetically outcompete endosomal capture. The original

  在本报告中，我们详细阐述了激活富含精氨酸的细胞穿透肽 (CPP) 的两个新概念。早些时候，我们认为排斥驱动的离子对与阴离子脂质的相互作用是它们穿过疏水性细胞膜的能力，并且疏水性阴离子如丁酸芘可以加速这一过程，从而在动力学上战胜内体捕获。最初解释芘丁酸酯的高活性可能源于 CPP 和活化剂之间的离子对-π 相互作用，这意味着用极化推拉芳烃取代 π-碱性芘应该提供更强大的 CPP 活化剂。为了详细说明这一假设，我们准备了一小部分阴离子两亲物，它们可以通过离子对-π 相互作用识别阳离子。与理论预测一致，我们发现平行但非反平行的离子对-π 相互作用在模型膜和细胞中提供了可操作的 CPP 激活剂。使用全氟化脂肪酸探索了芘丁酸酯的高活性可能源于膜中的自组装的替代建议。它们的亲氟性有望促进膜中的自组装，而它们的高酸度应防止响应自组装的电荷中和，即产生排斥驱动的离子对相互作用。与这些预期一致，我们发现全氟脂肪酸是