1-aminoanthraquinone | 1422011-37-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-aminoanthraquinone
• 英文别名: 1-Aminoanthracene-9,10(4aH,9aH)-dione；1-amino-4a,9a-dihydroanthracene-9,10-dione
• CAS: 1422011-37-7
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: VGZDTJXEKDJBNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-aminoanthraquinone 在 吡啶 、 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Novel aromatic–polyamine conjugates as cholinesterase inhibitors with notable selectivity toward butyrylcholinesterase

  摘要：

  Three types of aromatic-polyamine conjugates (6a-6s) were designed, synthesized and evaluated as potential inhibitors for cholinesterases (ChEs). The results showed that anthraquinone-polyamine conjugates (AQPCs) exhibited the most potent acetylcholinesterase (AChE) inhibitory activity with IC50 values from 1.50 to 11.13 mu M. Anthracene-polyamine conjugates (APCs) showed a surprising selectivity (from 76- to 3125-fold) and were most potent at inhibiting butyrylcholinesterase (BChE), with IC50 values from 0.016 to 0.657 mu M. A Lineweaver-Burk plot and molecular modeling studies indicated that the representative compounds, 6l and 6k, targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of ChEs. Furthermore, APCs did not affect HepG2 cell viability at the concentration of 100 mu M. Consequently, these polyamine conjugates could be thoroughly and systematically studied for the treatment of AD. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.045

文献信息

• A One-Pot Method for the Iodination of Aryl Amines via Stable Aryl Diazonium Silica Sulfates Under Solvent-Free Conditions
  作者：Amin Zarei、Abdol Hajipour、Leila Khazdooz

  DOI：10.1055/s-0028-1087981

  日期：——

  A convenient and rapid one-pot method for the synthesis of iodoarenes is developed which involves the sequential diazotization-iodination of aromatic amines with sodium nitrite, silica sulfuric acid and potassium iodide under solvent-free conditions at room temperature. Various aromatic amines possessing electron-withdrawing groups or electron-donating groups are converted into the corresponding aryl iodides in good yields.

  开发了一种便捷而快速的一锅法合成碘代芳烃的方法，该方法在室温下无溶剂条件下，通过芳香胺与亚硝酸钠、硅硫酸和碘化钾的顺序重氮化-碘化反应进行。多种具有吸电子基团或给电子基团的芳香胺均能以良好产率转化为相应的芳基碘化物。
• [EN] DISPERSE AZO DYES, A PROCESS FOR THE PREPARATION THEREOF AND THE USE THEREOF<br/>[FR] COLORANTS AZOÏQUES DISPERSÉS, LEUR PROCÉDÉ DE PRÉPARATION ET LEUR UTILISATION
  申请人：HUNTSMAN ADV MAT SWITZERLAND

  公开号：WO2021144304A1

  公开（公告）日：2021-07-22

  The present invention relates to azo dyes of formula (1), wherein D is a radical of formula (2) or (3), R1 and R2 independently denote hydrogen; C6–C10aryl which is unsubstituted or substituted by cyano, carboxy, hydroxy, halogen, C1–C6alkyl, or C1–C6alkoxy; C1–C12alkyl which may be interrupted one or more times by -O-, -S-, -NR4-, -CO-, -COO- or –OOC-, and is unsubstituted or substituted by cyano, carboxy, hydroxy, C6–C10aryl, or C6–C10aryloxy, which C6–C10aryl or C6–C10aryloxy is unsubstituted or substituted by cyano, carboxy, hydroxy, halogen, C1–C6alkyl, or C1–C6alkoxy; R3 and R4 are each independently of the other hydrogen, halogen, nitro, cyano, trifluoromethyl, carboxy, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylcarbonyl, C6–C10arylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylsulfonyl, C1-C6alkylsulfonylamino or C1-C4alkanoylamino; and R5 is halogen, nitro, cyano, trifluoromethyl, carboxy, C1-C6alkyl, C1-C6alkoxy, C1- C6alkylcarbonyl, C6–C10arylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylsulfonyl, C1-C6alkylsulfonylamino or C1-C4alkanoylamino; and R6, R7, R8 and R9 independently of each other are hydrogen, hydroxy, halogen, cyano, nitro or C1-C4alkanoylamino, and the radicals X independently denote N or C-H, with the proviso that at least one radical X denotes C-H, which are distinguished by their good lightfastness properties.

  本发明涉及式（1）的偶氮染料，其中D是式（2）或（3）的基团，R1和R2独立地表示氢；C6-C10芳基，其未取代或取代为氰基，羧基，羟基，卤素，C1-C6烷基或C1-C6烷氧基；C1-C12烷基，可被-O-，-S-，-NR4-，-CO-，-COO-或-OOC-中的一个或多个中断，并且未取代或取代为氰基，羧基，羟基，C6-C10芳基或C6-C10芳氧基，其中C6-C10芳基或C6-C10芳氧基未取代或取代为氰基，羧基，羟基，卤素，C1-C6烷基或C1-C6烷氧基；R3和R4各自独立地表示氢，卤素，硝基，氰基，三氟甲基，羧基，C1-C6烷基，C1-C6烷氧基，C1-C6烷基羰基，C6-C10芳基羰基，C1-C6烷氧基羰基，C1-C6烷基磺酰基，C1-C6烷基磺酰胺基或C1-C4烷酰胺基；R5表示卤素，硝基，氰基，三氟甲基，羧基，C1-C6烷基，C1-C6烷氧基，C1-C6烷基羰基，C6-C10芳基羰基，C1-C6烷氧基羰基，C1-C6烷基磺酰基，C1-C6烷基磺酰胺基或C1-C4烷酰胺基；R6，R7，R8和R9各自独立地表示氢，羟基，卤素，氰基，硝基或C1-C4烷酰胺基，基团X独立地表示N或C-H，但至少有一个基团X表示C-H，这些染料具有良好的耐光性能。