6-(N,N-dimethylamino)-2-[2-(2-hydroxyethoxy)ethyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione | 1051372-99-6

• 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-(N,N-dimethylamino)-2-[2-(2-hydroxyethoxy)ethyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 6-(dimethylamino)-2-[2-(2-hydroxyethoxy)ethyl]benzo[de]isoquinoline-1,3-dione
• CAS: 1051372-99-6
• 化学式: C₁₈H₂₀N₂O₄
• 分子量: 328.368
• InChiKey: LSYLDUKVTLDQMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(N,N-dimethylamino)-2-[2-(2-hydroxyethoxy)ethyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione 、 吲哚美辛 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以70%的产率得到2-{2-[6-(dimethylamino)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl]ethoxy}ethyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
  参考文献：
  名称：

  Novel naphthalimide–indomethacin hybrids as potential antitumor agents: effects of linkers on hypoxic/oxic cytotoxicity and apoptosis-inducing activity

  摘要：

  A series of novel naphthalimide-indomethacin hybrids with different linkers were designed and synthesized. Their antitumor activity was evaluated against HeLa, A549, P388, HL-60, MCF-7, HCT-8, and A375 cancer cell lines in vitro. Preliminary results showed that the hybrids had moderate cytotoxic activity with 50% inhibition concentration (IC50) values of similar to 10(-5) M, and could effectively induce apoptosis in HeLa cells. More importantly, the amide derivatives had better cytotoxic and proapoptotic activity than their ester counterparts, whereas the ester derivatives had hypoxic preferred cytotoxicity and might be used as promising candidates of prodrug in hypoxic tumor cells. This work provides a novel class of naphthalimide-indomethacin hybrids with unique antitumor activity for further optimization.

  DOI：

  10.1007/s00706-010-0337-x
• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 在 copper(ll) sulfate pentahydrate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 6-(N,N-dimethylamino)-2-[2-(2-hydroxyethoxy)ethyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Novel naphthalimide–indomethacin hybrids as potential antitumor agents: effects of linkers on hypoxic/oxic cytotoxicity and apoptosis-inducing activity

  摘要：

  A series of novel naphthalimide-indomethacin hybrids with different linkers were designed and synthesized. Their antitumor activity was evaluated against HeLa, A549, P388, HL-60, MCF-7, HCT-8, and A375 cancer cell lines in vitro. Preliminary results showed that the hybrids had moderate cytotoxic activity with 50% inhibition concentration (IC50) values of similar to 10(-5) M, and could effectively induce apoptosis in HeLa cells. More importantly, the amide derivatives had better cytotoxic and proapoptotic activity than their ester counterparts, whereas the ester derivatives had hypoxic preferred cytotoxicity and might be used as promising candidates of prodrug in hypoxic tumor cells. This work provides a novel class of naphthalimide-indomethacin hybrids with unique antitumor activity for further optimization.

  DOI：

  10.1007/s00706-010-0337-x

文献信息

• Quaternary Piperazine-Substituted Rhodamines with Enhanced Brightness for Super-Resolution Imaging
  作者：Zhiwei Ye、Wei Yang、Chao Wang、Ying Zheng、Weijie Chi、Xiaogang Liu、Zhenlong Huang、Xiaoyuan Li、Yi Xiao

  DOI：10.1021/jacs.9b04893

  日期：2019.9.18

  rhodamine dyes exhibit suboptimal brightness due to the formation of twisted intramolecular charge transfer (TICT) upon photoexcitation. Herein, we have developed a new class of quaternary piperazine substituted rhodamines with outstanding quantum yields (Φ = 0.93) and superior brightness (ε×Φ = 8.1 × 104 L∙mol-1∙cm-1), by utilizing the electronic inductive effect to prevent TICT. We have also successfully

  荧光团的亮度不足是超分辨率显微镜发展的主要瓶颈。尽管被广泛使用，但由于在光激发时形成扭曲的分子内电荷转移 (TICT)，许多罗丹明染料表现出次优的亮度。在此，我们利用电子感应效应开发了一类具有优异量子产率 (Φ = 0.93) 和优异亮度 (ε×Φ = 8.1 × 104 L∙mol-1∙cm-1) 的新型季哌嗪取代罗丹明以防止 TICT。我们还成功地将这些罗丹明用于固定细胞微管、细胞膜和活 HeLa 细胞溶酶体的超分辨率成像。最后，我们证明了这种策略可推广到其他荧光团家族，从而大大提高了量子产率。
• ENVIRONMENTALLY SENSITIVE FLUOROPHORES
  申请人：Imperiali Barbara

  公开号：US20100168428A1

  公开（公告）日：2010-07-01

  The present invention generally relates to environment-sensitive fluorophores, including environment-sensitive fluorophores for reporting protein/protein and peptide/protein interactions. In one aspect, the present invention is directed to compounds and salts thereof, compositions and methods useful in determining biological interactions. In some cases, the compounds of the present invention are environment-sensitive fluorophores that have spectroscopic behavior that may depend on factors such as the physicochemical properties of the surrounding environment. The compounds of the present invention can be used, in certain embodiments, to monitor ions, small molecules, and biological processes such as protein folding, protein-protein interactions and phosphorylation events.
• US8440835B2
  申请人：——

  公开号：US8440835B2

  公开（公告）日：2013-05-14
• [EN] ENVIRONMENTALLY SENSITIVE FLUOROPHORES<br/>[FR] FLUOROPHORES SENSIBLES À L'ENVIRONNEMENT
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2008106104A2

  公开（公告）日：2008-09-04

  [EN] The present invention generally relates to environment-sensitive fluorophores, including environment-sensitive fluorophores for reporting protein/protein and peptide/protein interactions. In one aspect, the present invention is directed to compounds and salts thereof, compositions and methods useful in determining biological interactions. In some cases, the compounds of the present invention are environment- sensitive fluorophores that have spectroscopic behavior that may depend on factors such as the physicochemical properties of the surrounding environment. The compounds of the present invention can be used, in certain embodiments, to monitor ions, small molecules, and biological processes such as protein folding, protein-protein interactions and phosphorylation events.
  [FR] L'invention concerne des fluorophores sensibles à l'environnement, y compris des fluorophores sensibles à l'environnement pour signaler des interactions protéine/protéine et peptide/protéine. Selon un aspect, la présente invention concerne des compositions et des sels de ceux-ci, des compositions et des procédés utiles pour déterminer des interactions biologiques. Dans certains cas, les composés de la présente invention sont des fluorophores sensibles à l'environnement qui ont un comportement spectroscopique qui peut dépendre de facteurs tels que les propriétés physico-chimiques de l'environnement environnant. Les composés de la présente invention peuvent être utilisés, selon certains modes de réalisation, pour surveiller des ions, de petites molécules, et des processus biologiques tels qu'un repliement de protéines, des interactions protéine/protéine et des événements de phosphorylation.
• Novel naphthalimide–indomethacin hybrids as potential antitumor agents: effects of linkers on hypoxic/oxic cytotoxicity and apoptosis-inducing activity
  作者：Aibin Wu、Yufang Xu、Xuhong Qian

  DOI：10.1007/s00706-010-0337-x

  日期：2010.8

  A series of novel naphthalimide-indomethacin hybrids with different linkers were designed and synthesized. Their antitumor activity was evaluated against HeLa, A549, P388, HL-60, MCF-7, HCT-8, and A375 cancer cell lines in vitro. Preliminary results showed that the hybrids had moderate cytotoxic activity with 50% inhibition concentration (IC50) values of similar to 10(-5) M, and could effectively induce apoptosis in HeLa cells. More importantly, the amide derivatives had better cytotoxic and proapoptotic activity than their ester counterparts, whereas the ester derivatives had hypoxic preferred cytotoxicity and might be used as promising candidates of prodrug in hypoxic tumor cells. This work provides a novel class of naphthalimide-indomethacin hybrids with unique antitumor activity for further optimization.