4-(naphthalene-1-ylamino)-4-oxo-butanoic acid | 37642-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(naphthalene-1-ylamino)-4-oxo-butanoic acid
• 英文别名: 4-(naphthalen-1-ylamino)-4-oxobutanoic acid；4-(1-Naphthylamino)-4-oxobutanoic acid
• CAS: 37642-93-6
• 化学式: C₁₄H₁₃NO₃
• mdl: MFCD00224189
• 分子量: 243.262
• InChiKey: FXJMMPAVUBUMAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924299090

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 4-(naphthalene-1-ylamino)-4-oxo-butanoic acid
  参考文献：
  名称：

  Pellizzari; Matteucci, Justus Liebigs Annalen der Chemie, 1888, vol. 248, p. 159

  摘要：

  DOI：

文献信息

• Design, synthesis and anticancer activity of naphthoquinone derivatives
  作者：Xiao-bao Shen、Yang Wang、Xuan-zhen Han、Liang-quan Sheng、Fu-fang Wu、Xinhua Liu

  DOI：10.1080/14756366.2020.1740693

  日期：2020.1.1

  were designed and synthesised. With the help of reverse targets searching, anti-cancer activity was preliminarily evaluated, most of them are effective against some tumour cells, especially compound 12: 1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl-4-oxo-4-((4-phenoxyphenyl)amino) butanoate whose IC50 against SGC-7901 was 4.1 ± 2.6 μM. Meanwhile the anticancer mechanism

  摘要 基于萘醌部分的分子对接和药效团分析，总共设计和合成了23种化合物。借助反向靶标搜索，初步评估了其抗癌活性，其中大多数对某些肿瘤细胞有效，尤其是化合物12：1-（5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen -2-基）-4-甲基戊-3-烯-1-基-4-氧代-4-（（4-苯氧基苯基）氨基）丁酸酯，其对SGC-7901的IC 50为4.1±2.6μM。同时通过AnnexinV / PI染色，免疫荧光，Western印迹分析和分子对接研究了化合物12的抗癌机理。结果表明该化合物可能通过调节PI3K信号通路诱导细胞凋亡和细胞自噬。
• 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。
• Synthesis and binding study of certain 6-arylalkanamides as molecular probes for cannabinoid receptor subtypes
  作者：Azza T. Taher、Hanan H. Kadry、Marco Allarà、Vincenzo Di Marzo、Ashraf H. Abadi、Khaled A. Abouzid

  DOI：10.3109/14756366.2011.645241

  日期：2013.6.1

  and psychomimetic actions, however, their potential for abuse have dampened enthusiasm for their therapeutic development. In an effort to refine a semi-rigid structural framework for CB(2) receptors binding, we designed novel compounds based on aromatic moiety and flexible linker with various amides mimicking the outlook of the endogenous anandamide which could provide as CB(2) receptor ligand. In this

  四氢大麻酚和其他混合大麻素（CB）受体CB（1）/ CB（2）受体激动剂已被广泛确立以引发抗伤害作用和拟精神行为，但是，其滥用的潜力已削弱了其治疗发展的热情。为了努力完善CB（2）受体结合的半刚性结构框架，我们设计了基于芳香族部分和柔性接头的新型化合物，以及各种酰胺，这些酰胺模仿了内源性anandamide的前景，可以作为CB（2）受体配体提供。在这个方向上，我们开发并合成了带有不同头基的新型芳基或亚芳基己酸酰胺和芳基链烷酸二酰胺。测试了这些新化合物对人重组CB受体CB（1）和CB（2）和脂肪酸酰胺水解酶的亲和力。虽然，
• METHOD FOR OBTAINING NOVEL DERIVATIVES OF NAPHTHALENE FOR THE IN VIVO DIAGNOSIS OF ALZHEIMER'S DISEASE
  申请人：Sablon Carrazana Marquiza

  公开号：US20150217005A1

  公开（公告）日：2015-08-06

  This invention relates to a chemistry branch, particularly to the field of compounds' organic synthesis that belong 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.

  本发明涉及化学分支，特别是属于芳香族双环或萘类化合物有机合成领域，用于淀粉样板的检测。这些新的萘衍生物具有下列一般式：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-二硫代氨基酸盐。术语“烷基”和“烷基烷基”指线性或支链脂肪链，最好是1到4个碳原子，卤素一词指氟、溴或碘。这些化合物是中性、亲脂性和分子量低，因此它们可以穿过血脑屏障并附着在淀粉样板上。本发明提供了获得萘衍生物的程序，其收率良好，可以实用、经济并适用于更大规模的制造。