2-(naphthalen-1-ylamino)naphthalene-1,4-dione | 110051-02-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(naphthalen-1-ylamino)naphthalene-1,4-dione
• 英文别名: 2-(Naphthalen-1-ylamino)naphthalene-1,4-dione
• CAS: 110051-02-0
• 化学式: C₂₀H₁₃NO₂
• 分子量: 299.329
• InChiKey: GLCHQFOBIDMGAW-UHFFFAOYSA-N

物化性质

• 沸点：
  509.9±50.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(naphthalen-1-ylamino)naphthalene-1,4-dione 、 N-allyl-2-bromo-N-(4-bromophenyl)-2,2-difluoroacetamide 在 五甲基二乙烯三胺 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以62%的产率得到2-((1-(4-bromophenyl)-4,4-difluoro-5-oxopyrrolidin-3-yl)methyl)-3-(naphthalen-1-ylamino)naphthalene-1,4-dione
  参考文献：
  名称：

  光诱导的EDA配合物可以使未活化的烯烃与2-Amino-1,4-萘醌进行自由基串联环化/芳基化

  摘要：

  已经开发了在没有外部光催化剂的情况下在2-氨基-1、4-萘醌和N-烯丙基-2-溴-2,2-二氟乙酰胺之间的可见光诱导的自由基串联环化/芳基化。该转化可以在室温下进行，并以中等至优异的产率得到各种C-3-官能化的2-氨基-1,4-萘醌衍生物。此外，机理研究表明，反应是由电子供体-受体（EDA）配合物的形成驱动的。

  DOI：

  10.1021/acs.orglett.1c00268
• 作为产物：
  描述：

  萘酚 在 2,2-difluoro-5,11-diiodo-6,10-dimethyl-8-phenyl-4,12-bis(2-phenylethenyl)-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene 、 copper diacetate 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 3.5h， 生成 2-(naphthalen-1-ylamino)naphthalene-1,4-dione
  参考文献：
  名称：

  Bodipy Derivatives as Organic Triplet Photosensitizers for Aerobic Photoorganocatalytic Oxidative Coupling of Amines and Photooxidation of Dihydroxylnaphthalenes

  摘要：

  We used iodo-Bodipy derivatives that show strong absorption of visible light and long-lived triplet excited states as organic catalysts for photoredox catalytic organic reactions. Conventionally most of the photocatalysts are based on the off-the-shelf compounds, usually showing weak absorption in the visible region and short triplet excited state lifetimes. Herein, the organic catalysts are used for two photocatalyzed reactions mediated by singlet oxygen (O-1(2)), that is, the aerobic oxidative coupling of amines and the photooxidation of dihydroxylnaphthalenes, which is coupled to the subsequent addition of amines to the naphthoquinones, via C-H functionalization of 1,4-naphthoquinone, to produce N-aryl-2-amino-1,4-naphthoquinones (one-pot reaction), which are anticancer and antibiotic reagents. The photoreactions were substantially accelerated with these new iodo-Bodipy organic photocatalysts compared to that catalyzed with the conventional Ru(II)/Ir(III) complexes, which show weak absorption in the visible region and short-lived triplet excited states. Our results will inspire the design and application of new organic triplet photosensitizers that show strong absorption of visible light and longlived triplet excited state and the application of these catalysts in photoredox catalytic organic reactions.

  DOI：

  10.1021/jo400769u

文献信息

• Exploration of Benzo[b]carbazole-6,11-diones as anticancer agents: Synthesis and studies of hTopoIIα inhibition and apoptotic effects
  作者：Shailendra Sisodiya、Subarno Paul、Hiteshkumar Chaudhary、Preeti Grewal、Gulshan Kumar、Divine P Daniel、Biswajit Das、Deepika Nayak、Sankar K. Guchhait、Chanakya N. Kundu、Uttam C. Banerjee

  DOI：10.1016/j.bmcl.2021.128274

  日期：2021.10

  cells (MCF 10A). Some of the active compounds were evaluated for clonogenic cell survival and apoptotic effects in cancer cells (DAPI nuclear staining, Comet assay, Annexin-V-FITC/PI dual staining, flow cytometry, and western blot analysis with relevant proteins). All compounds were tested for hTopoIIα inhibitory activity. The investigated series compounds showed important properties like significant

  两个系列的（杂）芳基氨基萘醌和苯并稠合咔唑醌被考虑用于研究，理由是相关的结构基序存在于许多药物、临床试验药物、天然产物和 hTopoIIα 抑制剂中。通过脱氢C N 和Pd催化C反应共合成42种化合物C 键形成转换。这些化合物针对多种癌细胞进行了筛选，包括高度转移的癌细胞（MCF-7、MDA-MB-231、H-357 和 HEK293T）和正常细胞（MCF 10A）。评估了一些活性化合物在癌细胞中的克隆形成细胞存活和细胞凋亡效应（DAPI 核染色、彗星试验、膜联蛋白-V-FITC/PI 双染色、流式细胞术和相关蛋白质的蛋白质印迹分析）。测试所有化合物的 hTopoIIα 抑制活性。研究的系列化合物显示出重要的特性，例如在 S 期细胞周期停滞的癌细胞中显着的细胞凋亡抗增殖和下调 NF-κβ 信号级联，对正常细胞的细胞毒性相对较小，与抗癌药物依托泊苷相比，抑制 hTopoIIα 的效率更高.
• <i>t</i>-BuOK mediated oxidative coupling amination of 1,4-naphthoquinone and related 3-indolylnaphthoquinones with amines
  作者：Yu Dong、Ting Mei、Qi-Qi Luo、Qiang Feng、Bo Chang、Fan Yang、Hong-wei Zhou、Zhi-Chuan Shi、Ji-Yu Wang、Bing He

  DOI：10.1039/d1ra00193k

  日期：——

  3-indolylnaphthoquinones with amines, such as various (hetero)aromatic amine and aliphatic amine via t-BuOK-mediated oxidative coupling at room temperature has been developed. This reaction provides efficient access to the biologically important and synthetically useful 2-amino-1,4-naphthoquinones and 2-amino-3-indolylnaphthoquinones with good yields under mild conditions. The present protocol is simple

  1,4-萘醌和相关的 3-吲哚基萘醌与胺（例如各种（杂）芳香胺和脂肪胺）在室温下通过 t -BuOK 介导的氧化偶联进行无过渡金属胺化。该反应可以在温和条件下以良好的收率有效地获得具有重要生物学意义和合成用途的2-氨基-1,4-萘醌和2-氨基-3-吲哚基萘醌。本方案简单实用，具有良好的官能团耐受性。此外，将所得2-氨基-3-吲哚基萘醌进一步转化合成多环N-杂环。
• 2-Phenylaminonaphthoquinones and related compounds: Synthesis, trypanocidal and cytotoxic activities
  作者：Ivan Sieveking、Pablo Thomas、Juan C. Estévez、Natalia Quiñones、Mauricio A. Cuéllar、Juan Villena、Christian Espinosa-Bustos、Angélica Fierro、Ricardo A. Tapia、Juan D. Maya、Rodrigo López-Muñoz、Bruce K. Cassels、Ramon J. Estévez、Cristian O. Salas

  DOI：10.1016/j.bmc.2014.07.030

  日期：2014.9

  A series of new 2-aminonaphthoquinones and related compounds were synthesized and evaluated in vitro as trypanocidal and cytotoxic agents. Some tested compounds inhibited epimastigote growth and trypomastigote viability. Several compounds showed similar or higher activity and selectivity as compared with current trypanocidal drug, nifurtimox. Compound 4l exhibit higher selectivity than nifurtimox against

  合成了一系列新的2-氨基萘醌和相关化合物，并在体外评估了其为锥虫和细胞毒剂。一些经过测试的化合物抑制了前鞭毛体的生长和锥鞭毛体的生存能力。与目前的锥虫杀灭药硝呋替莫相比，几种化合物显示出相似或更高的活性和选择性。与Vero细胞相比，化合物4l对尼古丁对克鲁斯锥虫的选择性更高。测试了一些合成的醌类对癌细胞和正常成纤维细胞的影响，表明萘醌部分的某些化学修饰可诱导并显着提高细胞毒性的选择性指数（4g和10）。此处给出的结果表明，2-氨基萘醌衍生物的抗T. cruzi活性可以通过用吡啶部分取代苯环来提高。有趣的是，C-3上存在氯原子和高度亲脂性烷基或芳环是新近观察到的元素，应导致发现更具选择性的细胞毒性和锥虫性化合物。
• A One-Pot Approach to 2-(N-Substituted Amino)-1,4-naphthoquinones with Use of Nitro Compounds and 1,4-Naphthoquinones in Water
  作者：Ji-Yu Wang、Xu-Ling Chen、Yu Dong、Shuai He、Rui Zhang、Hua Zhang、Lei Tang、Xiao-Mei Zhang

  DOI：10.1055/s-0037-1610689

  日期：2019.3

  A one-pot synthesis of 2-(N-substituted amino)-1,4-naphthoquinones from 1,4-naphthoquinones and nitro compounds in water has been developed. This method features mild reaction conditions and provides aromatic nitro compounds with various functional groups such as halogens, methylthio, ester, amide, even allyl, propargyl, and heterocycles, as well as aliphatic nitro compounds that are well tolerated

  已开发出从 1,4-萘醌和硝基化合物在水中一锅法合成 2-(N-取代氨基)-1,4-萘醌。该方法的特点是反应条件温和，提供具有各种官能团的芳香硝基化合物，如卤素、甲硫基、酯、酰胺，甚至烯丙基、炔丙基和杂环，以及耐受性良好的脂肪族硝基化合物。该方法可以扩大规模，我们将获得的 2-(N-取代氨基)-1,4-萘醌进一步转化以合成咔唑醌衍生物。
• [EN] COMPOSITIONS AND METHODS FOR TREATING NEUROLOGICAL DISEASES OR INJURY<br/>[FR] COMPOSITIONS ET MÉTHODES DE TRAITEMENT DE MALADIES OU DE LÉSIONS NEUROLOGIQUES
  申请人：MUSC FOUND FOR RES DEV

  公开号：WO2014074976A1

  公开（公告）日：2014-05-15

  Provided are compounds for the treatment of neurological diseases or injuries, including neurodegenerative diseases, stroke, trauma, epilepsy, acute and chronic kidney injuries, diabetes mellitus, and/or seizures. In some embodiments, derivatives of vitamin K are provided.

  提供了用于治疗神经系统疾病或损伤的化合物，包括神经退行性疾病、中风、创伤、癫痫、急性和慢性肾脏损伤、糖尿病和/或癫痫。在某些实施例中，提供了维生素K的衍生物。