2-(2-hydroxyethyl)-6-methoxy-1H-benzo[de]isoquinoline-1,3(2H)-dione | 36780-19-5

• 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: 2-(2-hydroxyethyl)-6-methoxy-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 4-methoxy-N-(2-hydroxyethyl)-1,8-naphthalimide；2-(2-hydroxyethyl)-6-methoxybenzo[de]isoquinoline-1,3-dione
• CAS: 36780-19-5
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: NZMTVWXZWQTBSU-UHFFFAOYSA-N

物化性质

• 沸点：
  507.6±35.0 °C(Predicted)
• 密度：
  1.385±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxyethyl)-6-methoxy-1H-benzo[de]isoquinoline-1,3(2H)-dione 在 sodium azide 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Thiourea Modified Doxorubicin: A Perspective pH-Sensitive Prodrug

  摘要：

  提出了一种合成pH敏感前药的新方法：硫脲药物修饰。由此产生的前药能在肿瘤细胞酸性环境中释放出细胞毒素和生物活性2-硫乙内酰脲。通过FRET模型验证了硫脲在酸性催化下环化成2-硫乙内酰脲的概念。获得了模型叠氮胸苷、细胞毒素阿霉素和2-硫乙内酰脲阿布妥因的双前药，在酸性环境中能释放相应的药物。对前列腺癌细胞进行了所得阿霉素前药的测试，结果显示硫脲修饰的前药在pH 7.6中性环境下比阿霉素（IC50范围为0.01258至0.02559 μM）的细胞毒性低（平均IC50范围为0.5584至0.9885 μM），而在癌细胞的轻度酸性条件下与阿霉素（IC50范围为0.2303至0.8110 μM）的毒性相似（平均IC50范围为0.4970至0.7994 μM）。在PC3肿瘤细胞中，Dox前药的细胞内和核内积累远远高于游离阿霉素。

  DOI：

  10.1021/acs.bioconjchem.8b00885
• 作为产物：
  描述：

  5-溴苊 在 sodium dichromate dihydrate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 2-(2-hydroxyethyl)-6-methoxy-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Thiourea Modified Doxorubicin: A Perspective pH-Sensitive Prodrug

  摘要：

  提出了一种合成pH敏感前药的新方法：硫脲药物修饰。由此产生的前药能在肿瘤细胞酸性环境中释放出细胞毒素和生物活性2-硫乙内酰脲。通过FRET模型验证了硫脲在酸性催化下环化成2-硫乙内酰脲的概念。获得了模型叠氮胸苷、细胞毒素阿霉素和2-硫乙内酰脲阿布妥因的双前药，在酸性环境中能释放相应的药物。对前列腺癌细胞进行了所得阿霉素前药的测试，结果显示硫脲修饰的前药在pH 7.6中性环境下比阿霉素（IC50范围为0.01258至0.02559 μM）的细胞毒性低（平均IC50范围为0.5584至0.9885 μM），而在癌细胞的轻度酸性条件下与阿霉素（IC50范围为0.2303至0.8110 μM）的毒性相似（平均IC50范围为0.4970至0.7994 μM）。在PC3肿瘤细胞中，Dox前药的细胞内和核内积累远远高于游离阿霉素。

  DOI：

  10.1021/acs.bioconjchem.8b00885

文献信息

• Identification of Novel Antifungal Skeleton of Hydroxyethyl Naphthalimides with Synergistic Potential for Chemical and Dynamic Treatments
  作者：Pengli Zhang、Vijai Kumar Reddy Tangadanchu、Chenghe Zhou

  DOI：10.3390/molecules27238453

  日期：——

  The invasion of pathogenic fungi poses nonnegligible threats to the human health and agricultural industry. This work exploited a family of hydroxyethyl naphthalimides as novel antifungal species with synergistic potential of chemical and dynamic treatment to combat the fungal resistance. These prepared naphthalimides showed better antifungal potency than fluconazole towards some tested fungi including Aspergillus fumigatus, Candida tropicalis and Candida parapsilosis 22019. Especially, thioether benzimidazole derivative 7f with excellent anti-Candida tropicalis efficacy (MIC = 4 μg/mL) possessed low cytotoxicity, safe hemolysis level and less susceptibility to induce resistance. Biochemical interactions displayed that 7f could form a supramolecular complex with DNA to block DNA replication, and constitute a biosupermolecule with cytochrome P450 reductase (CPR) from Candida tropicalis to hinder CPR biological function. Additionally, 7f presented strong lipase affinity, which facilitated its permeation into cell membrane. Moreover, 7f with dynamic antifungal potency promoted the production and accumulation of reactive oxygen species (ROS) in cells, which destroyed the antioxidant defence system, led to oxidative stress with lipid peroxidation, loss of glutathione, membrane dysfunction and metabolic inactivation, and eventually caused cell death. The chemical and dynamic antifungal synergistic effect initiated by hydroxyethyl naphthalimides was a reasonable treatment window for prospective development.

  病原真菌的入侵对人类健康和农业造成了不可忽视的威胁。本研究利用羟乙基萘二甲酰亚胺家族作为新型抗真菌剂，通过化学和动态处理的协同潜力来对抗真菌的抗药性。与氟康唑相比，这些制备的萘二甲酰亚胺对一些受试真菌（包括烟曲霉、热带念珠菌和副丝状念珠菌 22019）表现出更好的抗真菌效力。尤其是硫醚苯并咪唑衍生物 7f，具有极佳的抗热带念珠菌效果（MIC = 4 μg/mL），而且细胞毒性低，溶血水平安全，不易产生抗药性。生化相互作用显示，7f 能与 DNA 形成超分子复合物，阻断 DNA 复制，并与热带念珠菌的细胞色素 P450 还原酶（CPR）构成生物超分子，阻碍 CPR 的生物功能。此外，7f 还具有很强的脂肪酶亲和力，有利于其渗透到细胞膜中。此外，具有动态抗真菌效力的 7f 还能促进细胞内活性氧（ROS）的产生和积累，从而破坏细胞的抗氧化防御系统，导致氧化应激引起脂质过氧化、谷胱甘肽损失、膜功能障碍和代谢失活，最终导致细胞死亡。羟乙基萘二甲酰亚胺引发的化学和动态抗真菌协同效应是一个合理的治疗窗口，具有发展前景。
• Photopolymerizable compositions including a polyurethane methacrylate polymer prepared using a polycarbonate diol, articles, and methods
  申请人：3M INNOVATIVE PROPERTIES COMPANY

  公开号：US11225535B2

  公开（公告）日：2022-01-18

  The present disclosure provides a photopolymerizable composition. The photopolymerizable composition includes a) 40-60 parts by weight of a monofunctional (meth)acrylate monomer, per 100 parts of the total photopolymerizable composition; b) a photoinitiator; and c) a polymerization reaction product of components. A cured homopolymer of the monofunctional (meth)acrylate monomer has a glass transition temperature of 125 degrees Celsius or greater. The polymerization reaction product of components includes i) a diisocyanate; ii) a hydroxy functional methacrylate; iii) a polycarbonate diol; and iv) a catalyst. The polymerization reaction product includes a polyurethane methacrylate polymer. Often, the polycarbonate diol has a number average molecular weight of greater than 1,000 grams per mole (g/mol) or a weighted average of all polycarbonate diols present in the components has a Mn of greater than 1,000 g/mol; alternatively, the polyurethane methacrylate polymer has a weight average molecular weight of 8,000 g/mol or greater. An article is also provided including the photopolymerizable composition reaction product. Further, the present disclosure provides articles and methods of making articles. Methods are additionally provided, including receiving, by a manufacturing device having one or more processors, a digital object comprising data specifying an article; and generating, with the manufacturing device by an additive manufacturing process, the article based on the digital object. A system is also provided, including a display that displays a 3D model of an article; and one or more processors that, in response to the 3D model selected by a user, cause a 3D printer to create a physical object of an article.

  本公开提供了一种可光聚合组合物。这种可光聚合组合物包括 a) 按重量计，每 100 份可光聚合组合物中含 40-60 份单官能团（甲基）丙烯酸酯单体；b) 光引发剂；以及 c) 各组分的聚合反应产物。单官能团（甲基）丙烯酸酯单体的固化均聚物的玻璃化温度为 125 摄氏度或更高。组分的聚合反应产物包括 i) 二异氰酸酯；ii) 羟基官能甲基丙烯酸酯；iii) 聚碳酸酯二元醇；和 iv) 催化剂。聚合反应产物包括聚氨酯甲基丙烯酸酯聚合物。通常，聚碳酸酯二元醇的数均分子量大于 1,000 克/摩尔（g/mol），或存在于组分中的所有聚碳酸酯二元醇的加权平均分子量大于 1,000 克/摩尔；或者，聚氨酯甲基丙烯酸酯聚合物的重量平均分子量大于或等于 8,000 克/摩尔。还提供了一种包括可光聚合组合物反应产物的物品。此外，本公开还提供了物品和制作物品的方法。另外还提供了方法，包括由具有一个或多个处理器的制造设备接收数字对象，该数字对象包括指定物品的数据；以及由制造设备通过增材制造工艺基于数字对象生成物品。还提供了一种系统，包括显示物品三维模型的显示器；以及一个或多个处理器，这些处理器响应用户选择的三维模型，使三维打印机创建物品的物理对象。
• Design, synthesis and pH sensing properties of novel 1,8-naphtalimide-based bichromophoric system
  作者：Nevena V. Marinova、Nikolai I. Georgiev、Vladimir B. Bojinov

  DOI：10.1016/j.jphotochem.2011.05.012

  日期：2011.7

  In this work we report on the design, synthesis and sensor properties of a novel bichromophoric sensor system based on 1,8-naphthalimide fluorophores. The synthesized dyad was configured as a fluorescent wavelength-shifting energy transfer chromophore. The novel donor-acceptor system contains blue emitting 4-methoxy-1,8-naphthalimide donor dye, capable of both absorbing light and efficiently transferring the energy to yellow-green emitting 4-N-methylpiperazinyl-1,8-naphthalimide acceptor. The energy-transfer efficiency in the dyad system was calculated to be more than 99%. The acceptor unit in the donor-acceptor system was also designed as a PET based sensor according to the "fluorophore-spacer-receptor" model. The fluorescence behaviour of the bichromophoric system was investigated as a function of pH. The fluorescence enhancement of the novel dyad in acidic media was more than 29 times indicating the high ability of the system to act as an efficient pH chemosensor. (C) 2011 Elsevier B.V. All rights reserved.
• PHOTOPOLYMERIZABLE COMPOSITIONS INCLUDING A POLYURETHANE METHACRYLATE POLYMER PREPARED USING A POLYCARBONATE DIOL, ARTICLES, AND METHODS
  申请人：3M INNOVATIVE PROPERTIES COMPANY

  公开号：US20210095056A1

  公开（公告）日：2021-04-01

  The present disclosure provides a photopolymerizable composition. The photopolymerizable composition includes a) 40-60 parts by weight of a monofunctional (meth)acrylate monomer, per 100 parts of the total photopolymerizable composition; b) a photoinitiator; and c) a polymerization reaction product of components. A cured homopolymer of the monofunctional (meth)acrylate monomer has a glass transition temperature of 125 degrees Celsius or greater. The polymerization reaction product of components includes i) a diisocyanate; ii) a hydroxy functional methacrylate; iii) a polycarbonate diol; and iv) a catalyst. The polymerization reaction product includes a polyurethane methacrylate polymer. Often, the polycarbonate diol has a number average molecular weight of greater than 1,000 grams per mole (g/mol) or a weighted average of all polycarbonate diols present in the components has a Mn of greater than 1,000 g/mol; alternatively, the polyurethane methacrylate polymer has a weight average molecular weight of 8,000 g/mol or greater. An article is also provided including the photopolymerizable composition reaction product. Further, the present disclosure provides articles and methods of making articles. Methods are additionally provided, including receiving, by a manufacturing device having one or more processors, a digital object comprising data specifying an article; and generating, with the manufacturing device by an additive manufacturing process, the article based on the digital object. A system is also provided, including a display that displays a 3D model of an article; and one or more processors that, in response to the 3D model selected by a user, cause a 3D printer to create a physical object of an article.
• ORTHODONTIC ARTICLES PREPARED USING A POLYCARBONATE DIOL, AND METHODS OF MAKING SAME
  申请人：3M INNOVATIVE PROPERTIES COMPANY

  公开号：US20210163664A1

  公开（公告）日：2021-06-03

  The present disclosure provides an orthodontic article including the reaction product of the photopolymerizable composition. The photopolymerizable composition includes i) a monofunctional (meth)acrylate monomer whose cured homopolymer has a glass transition temperature of 90 degrees Celsius or greater; ii) a photoinitiator; and iii) a polymerization reaction product of components. The components include 1) an isocyanate; 2) a (meth)acrylate mono-ol; 3) a polycarbonate diol; and 4) a catalyst. Further, the present disclosure provides a method of making an orthodontic article. The method includes obtaining a photopolymerizable composition and selectively curing the photopolymerizable composition to form an orthodontic article. Further, methods are provided, including receiving, by a manufacturing device having one or more processors, a digital object comprising data specifying an orthodontic article; and generating, with the manufacturing device by an additive manufacturing process, the orthodontic article based on the digital object. A system is also provided, including a display that displays a 3D model of an orthodontic article; and one or more processors that, in response to the 3D model selected by a user, cause a 3D printer to create a physical object of an orthodontic article.