9-anthraldehyde | 303019-69-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-anthraldehyde
• 英文别名: 4-(9-Anthrylmethyleneamino)-2,3-dimethyl-1-phenyl-3-pyrazoline-5-one；4-(anthracen-9-ylmethylideneamino)-1,5-dimethyl-2-phenylpyrazol-3-one
• CAS: 303019-69-4
• 化学式: C₂₆H₂₁N₃O
• mdl: MFCD00336446
• 分子量: 391.472
• InChiKey: RNXZNZGMBZVMDC-UHFFFAOYSA-N

物化性质

• 熔点：
  231-232 °C(Solv: methanol (67-56-1); chloroform (67-66-3))
• 沸点：
  580.2±60.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  35.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,10-菲罗啉 、 9-anthraldehyde 、 cobalt(II) chloride 以 乙醇 为溶剂， 反应 8.0h， 以75%的产率得到
  参考文献：
  名称：

  Design and synthesis of novel pyrazolone based coordination compounds: DNA synergy, biological screening, apoptosis, molecular docking and in-silico ADMET profile

  摘要：

  In this research, eight biologically significant novel mixed ligand complexes were prepared from 9-Anthraldehyde, 4-Aminoantipyrine, 1,10-Phenanthroline and metal chlorides. The synthesized compounds were characterized by different physicochemical and multispectral investigation and revealed that the compounds possess octahedral geometry with monomeric nature. The biological potential of compounds was analyzed by biological evaluation studies. DNA synergy techniques revealed that the prepared compounds are bound to the DNA through an intercalated pathway. Moreover, the DNA nuclease activity demonstrates that the synthesized compounds cleaved the pBR 322 DNA with H2O2. The antimicrobial screening of the compounds have performed against certain pathogens and reports explained that the complexes were excellent antipathogenic screeners. The anti-proliferative and free radical scavenging studies of synthesized compounds implied that compounds have an admirable anticancer skill as well as intense scavenger ability due to the presence of heterocyclic secondary ligand. The apoptosis analysis signified that synthesized complexes have outstanding aptitude on breast tumour cell lines and initiated the morphological changes leads to cell death. The ADMET prediction revealed that prepared compounds have greater drug-likeness proficiency. Molecular docking simulations have been analyzed to identify the binding affinity and the mode of interaction of the synthesized compounds with nucleic acid (1BNA) and Fibroblast Growth Factor Receptor (FGFR). (C) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2019.07.059
• 作为产物：
  描述：

  4-氨基安替比林 、 9-蒽甲醛 以 甲醇 为溶剂， 反应 7.0h， 以95%的产率得到9-anthraldehyde
  参考文献：
  名称：

  通过调节配体结构用于pic的皮摩尔检测，探索聚集诱导的发射。

  摘要：

  通过附加到安替比林上的稠环芳族部分中环数的受控变化来调节配体结构，可以通过与101倍荧光增强相关的聚集诱导发射（AIE）检测7.8×10-12 M pyr。在一种情况下，将安替比林单元替换为吡啶以衍生出双甲基蒽基甲基吡啶胺。通过单晶X射线衍射分析已经确认了四个分子的结构。其中，pyr-安替比林共轭物（L）受到pyr触发的光致电子转移（PET）抑制，从而导致水助AIE。

  DOI：

  10.1002/jmr.2771

文献信息

• Physicochemical and Nonlinear Optical Properties of Novel Environmentally Benign Heterocyclic Azomethine Dyes: Experimental and Theoretical Studies
  作者：S. M. Afzal、M. A. N. Razvi、Salman A. Khan、Osman I. Osman、Ahmed H. Bakry、Abdullah M. Asiri

  DOI：10.1371/journal.pone.0161613

  日期：——

  photophysical properties like, extinction coefficient, oscillator strength, stokes shift and transition dipole moment. This reflects physicochemical behaviors of synthesized dyes. In addition, their intramolecular charge transfer and nonlinear optical properties, supported by natural bond orbital technique, were also studied computationally by density functional theory. The negative nonlinear refractive

  蒽-9-甲醛与不同杂环胺在微波辐射下反应制备了新型杂环偶氮甲胺染料。偶氮甲碱染料的结构通过元素分析，质谱和几种光谱学技术得到证实。我们研究了偶氮甲胺染料在各种溶剂中的吸光度和荧光光谱。发现它们是良好的吸收体和发射体。我们还报告了光物理性质，如消光系数，振荡器强度，斯托克斯位移和跃迁偶极矩。这反映了合成染料的物理化学行为。此外，还通过密度泛函理论对它们的分子内电荷转移和非线性光学性质进行了自然键轨道技术的支持。使用闭孔和开孔Z扫描技术以及连续波氦氖激光，测量了这些染料的负非线性折射率和非线性吸收系数。发现它们随溶液浓度线性变化。
• Fe3+-selective fluorescent probe based on aminoantipyrine in aqueous solution
  作者：Yanmei Zhou、Hua Zhou、Junli Zhang、Lin Zhang、Jingyang Niu

  DOI：10.1016/j.saa.2012.08.025

  日期：2012.12

  A novel and simple Schiff base composed with 9-anthraldehyde and 4-aminoantipyrine was synthesized and characterized as a fluorescent probe. In the presence of Fe3+, the fluorescent intensity has a dramatic enhancement over other examined metal ions in aqueous solution. The method of Job's plot indicated the formation of 1:1 complex between probe and Fe3+, and the possible binding mode of the system was also proposed. Moreover, other examined metal ions had no effect on the detection of Fe3+. (C) 2012 Elsevier B.V. All rights reserved.
• Exploring aggregation‐induced emission through tuning of ligand structure for picomolar detection of pyrene
  作者：Milan Ghosh、Sabyasachi Ta、Sisir Lohar、Sudipta Das、Paula Brandão、Vitor Felix、Debasis Das

  DOI：10.1002/jmr.2771

  日期：2019.5

  Tuning of ligand structures through controlled variation of ring number in fused-ring aromatic moiety appended to antipyrine allows detection of 7.8 × 10-12 M pyrene via aggregation-induced emission (AIE) associated with 101-fold fluorescence enhancement. In one case, antipyrine unit is replaced by pyridine to derive bis-methylanthracenyl picolyl amine. The structures of four molecules have been confirmed

  通过附加到安替比林上的稠环芳族部分中环数的受控变化来调节配体结构，可以通过与101倍荧光增强相关的聚集诱导发射（AIE）检测7.8×10-12 M pyr。在一种情况下，将安替比林单元替换为吡啶以衍生出双甲基蒽基甲基吡啶胺。通过单晶X射线衍射分析已经确认了四个分子的结构。其中，pyr-安替比林共轭物（L）受到pyr触发的光致电子转移（PET）抑制，从而导致水助AIE。
• Design and synthesis of novel pyrazolone based coordination compounds: DNA synergy, biological screening, apoptosis, molecular docking and in-silico ADMET profile
  作者：S. Syed Ali Fathima、M. Mohamed Sahul Meeran、E.R. Nagarajan

  DOI：10.1016/j.molstruc.2019.07.059

  日期：2019.12

  In this research, eight biologically significant novel mixed ligand complexes were prepared from 9-Anthraldehyde, 4-Aminoantipyrine, 1,10-Phenanthroline and metal chlorides. The synthesized compounds were characterized by different physicochemical and multispectral investigation and revealed that the compounds possess octahedral geometry with monomeric nature. The biological potential of compounds was analyzed by biological evaluation studies. DNA synergy techniques revealed that the prepared compounds are bound to the DNA through an intercalated pathway. Moreover, the DNA nuclease activity demonstrates that the synthesized compounds cleaved the pBR 322 DNA with H2O2. The antimicrobial screening of the compounds have performed against certain pathogens and reports explained that the complexes were excellent antipathogenic screeners. The anti-proliferative and free radical scavenging studies of synthesized compounds implied that compounds have an admirable anticancer skill as well as intense scavenger ability due to the presence of heterocyclic secondary ligand. The apoptosis analysis signified that synthesized complexes have outstanding aptitude on breast tumour cell lines and initiated the morphological changes leads to cell death. The ADMET prediction revealed that prepared compounds have greater drug-likeness proficiency. Molecular docking simulations have been analyzed to identify the binding affinity and the mode of interaction of the synthesized compounds with nucleic acid (1BNA) and Fibroblast Growth Factor Receptor (FGFR). (C) 2019 Elsevier B.V. All rights reserved.