1-(1-naphthyl)-2,5-pyrrolidinedione | 69971-89-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(1-naphthyl)-2,5-pyrrolidinedione
• 英文别名: N-(1-naphthyl)succinimide；1-naphthalen-1-ylpyrrolidine-2,5-dione
• CAS: 69971-89-7
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: NIJWNEHRVSLYJB-UHFFFAOYSA-N

物化性质

• 熔点：
  147.5-149.5 °C
• 沸点：
  496.9±14.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  1-(1-naphthyl)-2,5-pyrrolidinedione 在 cesiumhydroxide monohydrate 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.5h， 生成 methyl-(2-[4-(1-naphthylamino)-4-oxobutanoylamino]ethyl)carbamoditionic acid sodium salt
  参考文献：
  名称：

  METHOD FOR OBTAINING NOVEL DERIVATIVES OF NAPHTALENE FOR THE IN VIVO DIAGNOSIS OF ALZHEIMER 'S DISEASE

  摘要：

  公开号：

  EP2436666B1
• 作为产物：
  描述：

  4-(naphthalene-1-ylamino)-4-oxo-butanoic acid 在 sodium acetate 、 乙酸酐 作用下， 反应 1.0h， 以38%的产率得到1-(1-naphthyl)-2,5-pyrrolidinedione
  参考文献：
  名称：

  Studies on the Synthesis and Crystal Structure of N-(1-Naphthyl)succinimide

  摘要：

  A modified two-step procedure for synthesis of N-(1-naphthyl)succinimide (NaS) was developed, and its single crystal was prepared for the first time. The molecular and crystal structures were characterized by XRD, FT-IR, (1)H NMR, DSC, etc. It has been found that the melting point (159-160.5 degrees C) of our product is ca 10 degrees C higher than the documented values, while the characteristic infrared absorption band of carbonyl group splits into two peaks (1705cm(-1)/1779cm(-1)) rather than one as reported in the references. These discrepancies were further examined by X-ray crystallographic analysis. Meanwhile, photophysical spectroscopy was found to be powerful to Study the molecular structure and crystal morphology of organic compound.

  DOI：

  10.3987/com-08-11632

文献信息

• Comparison of Copper(II) Acetate Promoted N-Arylation of 5,5-Dimethyl Hydantoin and Other Imides with Triarylbismuthanes and Aryl Boronic Acids
  作者：Helmut Hügel、Colin Rix、Karin Fleck

  DOI：10.1055/s-2006-949638

  日期：2006.9

  This work demonstrates that the copper acetate promoted N-arylation of imides with boronic acids can be employed as a ­major method for the synthesis of N3-aryl hydantoins.

  这项工作表明，使用乙酸铜促进的亚胺与硼酸的N-芳基化反应可以作为合成N3-芳基海因的主要方法。
• Organic Reactions in Ionic Liquids: Ionic Liquid-Promoted Efficient Synthesis of<i>N</i>-Alkyl and<i>N</i>-Arylimides
  作者：Zhen-Chu Chen、Zhang-Gao Le、Yi Hu、Qin-Guo Zheng

  DOI：10.1055/s-2004-822337

  日期：——

  In the ionic liquids [Bmim][PF6] or [Bmim][BF4], a series of succinimide, maleimide and phthalimide derivatives were synthesized from corresponding anhydrides with a variety of primary amines in excellent yield.

  在离子液体[Bmim][PF6]或[Bmim][BF4]中，一系列琥珀酰亚胺、马来酰亚胺和邻苯二甲酰亚胺衍生物从相应的酸酐和多种伯胺高效合成，产率优异。
• The Synthesis and Testing of α-(Hydroxymethyl)pyrroles as DNA Binding Agents
  作者：Derek C. Martyn、Andrew D. Abell

  DOI：10.1071/ch04183

  日期：——

  The α-(hydroxymethyl)pyrroles 16a and 16b were prepared and shown to be cytotoxic against the P388 cancer cell line. Ethyl 5-hydroxymethyl-1H-pyrrole-2-carboxylate 18 was inactive, demonstrating that an α-(hydroxymethyl)pyrrole group alone is not sufficient for activity. Compound 16b has been shown to bind to DNA with reasonable affinity.

  制备的 α-（羟甲基）吡咯 16a 和 16b 对 P388 癌细胞系具有细胞毒性。5- 羟甲基-1H-吡咯-2-羧酸乙酯 18 没有活性，这表明仅有α-（羟甲基）吡咯基团不足以产生活性。化合物 16b 以合理的亲和力与 DNA 结合。
• Method for Obtaining Novel Derivatives of Naphthalene for the In Vivo Diagnosis of Alzheimer's Disease
  申请人：Carrazana Marquiza Sablón

  公开号：US20120321560A1

  公开（公告）日：2012-12-20

  This invention relates to a chemistry branch, particularly to the field of compounds' organic synthesis that belongs to the aromatic bicyclic or naphthalene category, used in the detection of amyloid sheets. These new naphthalene derivatives have a general formula: Wherein R represents mutually independent groups. In I: R 1 :-alkylenyl-C(O)NH-alkylenyl-R 3 , -alkylenyl-C(O)O—R 4 , R 3 :—COOH, —OH, —SH, —NH 2 , -alkyl-NH-alkyl-N-dithiocarbamate alkaline earth metal salts, R 4 : H, succinimidyl group, R 2 : —H,-alkyl. In II: R 1 : -alkyl, -alkylenyl-halide-alkylenyl-hydroxyl-alkylenyl-O-aryl, —O-alkylsulfonate alkylenyl, R 2 : -halide-alkylenyl-O-aryl, -alkylenyl-O-alkylsulfonate, -alkylenyl-halide-, —CH(O), —HC═C(CN) 2 , —HC═CHNO 2 , -alkylenyl-NH 2 , -alkylenyl-NH-alkyl, -alkylenyl-alkyl-N-dithiocarbamate alkaline salts. The terms “alkyl” and “alkylenyl” refer to linear or branched aliphatic chains, preferably from 1 to 4 carbon atoms and the term halide to fluorine, bromine or iodine. These compounds are neutral, lipophilic and have low molecular weight and therefore they cross the blood brain barrier and attach to the amyloid sheets. The present invention provides procedures for obtaining naphthalene derivatives with good yields, which can be practical, economical and adapted to a larger-scale manufacturing. We are unaware whether the compounds presented in this invention have been previously reported.

  这项发明涉及化学领域，特别是属于芳香双环或萘类别的化合物有机合成领域，用于检测淀粉样蛋白片。这些新的萘衍生物具有一般公式：其中R代表相互独立的基团。在I中：R1：-烷基-C（O）NH-烷基-R3，-烷基-C（O）O—R4，R3：—COOH，—OH，—SH，—NH2，-烷基-NH-烷基-N-二硫代氨基甲酸盐，R4：H，琥珀酰亚胺基团，R2：—H，-烷基。在II中：R1：-烷基，-烷基卤代-烷基羟基-烷基-O-芳基，—O-烷基磺酸酯烷基，R2：-卤代-烷基-O-芳基，-烷基-O-烷基磺酸酯，-烷基卤代-，—CH（O），—HC═C（CN）2，—HC═CHNO2，-烷基-NH2，-烷基-NH-烷基，-烷基-烷基-N-二硫代氨基盐。术语“烷基”和“烷基烯基”指直链或支链脂肪链，最好是1到4个碳原子，卤代指氟、溴或碘。这些化合物是中性的、亲脂性的，具有低分子量，因此它们可以穿过血脑屏障并附着在淀粉样蛋白片上。本发明提供了获得萘衍生物的程序，其产率高，可以实用、经济，并适用于大规模生产。我们不知道本发明中提出的化合物是否已经被先前报道。
• A new naphthalene derivative with anti-amyloidogenic activity as potential therapeutic agent for Alzheimer's disease
  作者：Suchitil Rivera-Marrero、Alberto Bencomo-Martínez、Erika Orta Salazar、Marquiza Sablón-Carrazana、Laura García-Pupo、Florencia Zoppolo、Florencia Arredondo、Rosina Dapueto、María Daniela Santi、Ingrid Kreimerman、Tania Pardo、Laura Reyes、Lídice Galán、Samila León-Chaviano、Luis A. Espinosa-Rodríguez、Roberto Menéndez-Soto del Valle、Eduardo Savio、Sofía Díaz Cintra、Chryslaine Rodríguez-Tanty

  DOI：10.1016/j.bmc.2020.115700

  日期：2020.10

  The aggregation of β-amyloid peptides is associated to neurodegeneration in Alzheimer’s disease (AD) patients. Consequently, the inhibition of both oligomerization and fibrillation of β-amyloid peptides is considered a plausible therapeutic approach for AD. Herein, the synthesis of new naphthalene derivatives and their evaluation as anti-β-amyloidogenic agents are presented. Molecular dynamic simulations

  β-淀粉样肽的聚集与阿尔茨海默氏病（AD）患者的神经退行性疾病有关。因此，抑制β-淀粉样肽的低聚和原纤维化被认为是AD的合理治疗方法。在此，提出了新的萘衍生物的合成及其作为抗β淀粉样生成剂的评价。分子动力学模拟预测了化合物，Aβ1-42肽和原纤维之间热力学稳定的复合物的形成。在人小胶质细胞中，这些化合物抑制Aβ1-42肽的聚集。铅化合物8在小鼠脑离体测定中显示出对淀粉样斑块的高亲和力，并具有足够的log Poct / PBS值。化合物8还改善了3xTg-AD雌性小鼠大脑的认知功能并降低了海马β-淀粉样蛋白负担。总之，我们的结果表明8可能是AD的新型治疗剂。