9-(3,4-diaminophenyl)acridine | 35586-87-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-(3,4-diaminophenyl)acridine
• 英文别名: 4-acridin-9-yl-benzene-1,2-diamine；9-(3',4'-Diaminophenyl)-acridin；4-acridin-9-ylbenzene-1,2-diamine
• CAS: 35586-87-9
• 化学式: C₁₉H₁₅N₃
• 分子量: 285.348
• InChiKey: FDNJYHQGSCSGAU-UHFFFAOYSA-N

物化性质

• 熔点：
  280-282 °C
• 沸点：
  503.9±45.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-(3,4-diaminophenyl)acridine 在 sodium acetate 、 乙酸酐 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 1-[4-Acridin-9-yl-2-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione
  参考文献：
  名称：

  活性部位匹配的荧光探针，用于快速，直接检测活细胞中含硫磺酰的肽/蛋白质

  摘要：

  含硫磺酰的肽/蛋白质（VSPPs）在人类病理中起着至关重要的作用。能够在体内检测细胞内VSPP的荧光探针将成为探索某些疾病机理的有用工具。在这项研究中，通过调节荧光染料中两个马来酰亚胺基团的空间间隔，使其与人类硫氧还蛋白的保守氨基酸序列（–CGPC–）中包含的两个活性半胱氨酸残基的空间间隔相匹配，两个活性部位匹配的荧光探针，o ‐Dm‐Ac和m‐Dm-Ac，用于实时成像活细胞中的VSPP。结果，这两种探针可以快速响应小肽模型和还原的蛋白质，例如WCGPCK（W-6），WCGGPCK（W-7）和WCGGGPCK（W-8），还原的牛血清白蛋白（rBSA），和还原的硫氧还蛋白（rTrx）。此外，o -Dm-Ac与上述肽和蛋白质，尤其是W-7和rTrx，具有更高的结合敏感性。此外，o -Dm-Ac已成功用于在体外和活细胞中快速直接检测VSPP。因此，提出了一种新颖的探针设计策略，并将合成的探针成功地用于原位靶蛋白成像。

  DOI：

  10.1002/chem.201405349
• 作为产物：
  描述：

  吖啶 在 盐酸 、 sulfur 作用下， 以 乙醇 为溶剂， 生成 9-(3,4-diaminophenyl)acridine
  参考文献：
  名称：

  具有维生素B6和光活性a啶部分的铜（II）配合物的靶向光细胞毒性。

  摘要：

  铜（II）吡ido醛席夫碱络合物[Cu（L1 / L2）（B）] ClO4（1-4），其中HL1为4-（（（（2-（1H-咪唑-4-基）乙基）亚氨基）甲基）-5-（羟甲基）-2-甲基吡啶-3-醇（在1和2中），HL2是2-（（（2-（1H-咪唑-4-基）乙基）亚氨基）甲基）苯酚（在3中，4），B是11-（9-ac啶基）双吡啶[3,2-a：2'，3'-c]吩嗪（1和3中的acdppz），二吡啶基[3,2-a：2'，3合成，表征了'-c]吩嗪（2）和1,10-菲咯啉（4），并研究了它们在可见光下的光细胞毒性，细胞内定位，细胞摄取和DNA光裂解活性。配合物4通过X射线晶体学表征。具有acdppz作为光敏剂的配合物1和3在HeLa和MCF7细胞的可见光下显示出显着的光细胞毒性，IC50值<0.6μM，而在黑暗中则相对无毒。该复合物在明暗条件下均对非致瘤性HPL1D细胞无毒。从共聚焦显微镜下可以看出

  DOI：

  10.1016/j.ejmech.2016.07.003

文献信息

• The synthesis and evaluation of o-phenylenediamine derivatives as fluorescent probes for nitric oxide detection
  作者：M. John Plater、Iain Greig、Miep H. Helfrich、Stuart H. Ralston

  DOI：10.1039/b105953j

  日期：2001.10.11

  A series of molecular probes for the determination of nitric oxide (NO) have been prepared. Each probe consists of an anthracene, coumarin or acridine fluorophore coupled to an electron rich o-phenylenediamine group. The o-phenylenediamine group can be substituted with methyl or methoxy groups to enhance its electron rich nature. The fluorophore fluorescence is quenched by photoelectron transfer (PET) from the aromatic amine to the lowest unoccupied orbital of the excited state fluorophore. Reaction with nitrosating species converts the o-phenylenediamine group into an electron deficient benzotriazole derivative. This group has a higher oxidation potential and does not quench the fluorophore fluorescence by photoelectron transfer so that these products are highly fluorescent. Some benzotriazole derivatives were made preparatively by alternative synthetic routes. The formation of fluorescent probes was evaluated by treatment of the precursors with nitrous fumes and S-nitroso-N-acetylpenicillamine (SNAP).

  制备了一系列用于测定一氧化氮（NO）的分子探针。每个探针由与富电子邻苯二胺基团偶联的蒽、香豆素或吖啶荧光团组成。邻苯二胺基团可以被甲基或甲氧基取代以增强其富电子性质。通过从芳香胺到激发态荧光团的最低未占据轨道的光电子转移（PET），荧光团荧光被淬灭。与亚硝化物质的反应将邻苯二胺基团转化为缺电子苯并三唑衍生物。该基团具有较高的氧化电位，并且不会通过光电子转移猝灭荧光团的荧光，因此这些产品具有高荧光性。一些苯并三唑衍生物是通过替代合成路线制备的。通过用亚硝酸处理前体来评估荧光探针的形成 烟雾和 S-亚硝基-N-乙酰青霉胺 (SNAP)。
• Synthesis, structure, DNA binding and photocleavage activity of a ruthenium(II) complex with 11-(9-acridinyl)dipyrido[3,2-a:2′,3′-c]phenazine ligand
  作者：Mariappan Mariappan、Masahiko Suenaga、Abhik Mukhopadhyay、Pallepogu Raghavaiah、Bhaskar G. Maiya

  DOI：10.1016/j.ica.2011.06.042

  日期：2011.10

  In our search for new DNA intercalating ligands, a novel bifunctional intercalator 11-(9-acridinyl)dipyrido[3,2-a:2 ',3 '-c]phenazine, acdppz (has two potentially effective intercalators via dipyridophenazine(dppz) and acridine which are linked together via C-C bond) and its corresponding Ru(II) polypyridyl complex [Ru(phen)(2)(acdppz)](2+) (where phen = 1,10-phenanthroline) have been synthesized and characterized. The electrochemical behaviors of the ligand and its complex have been thoroughly examined. The structure of acdppz and [Ru(phen)(2)(acdppz)](2+) were determined by X-ray crystallography. From the crystal structure of the complex, we found that the dppz moiety is not coplanar with the acridine ring, having a dihedral angle of 64.79 in the acdppz. The selected bond lengths and angles for the crystal structure of [Ru(phen)(2)(acdppz)](2+) were compared to the geometry-optimized molecular structure of [Ru(phen)(2)(acdppz)](2+) derived by Gaussian. The interaction of [Ru(phen)(2)(acdppz)](2+) with calfthymus (CT) DNA was investigated by absorption and viscometry titration, thermal denaturation studies. The above measurements indicated that the complex binds less strongly with the CT DNA due to the intercalation by the ruthenium bound acdppz with an intrinsic binding constant of 2.6 x 10(5) M-1. Molecular-modeling studies also support an intercalative mode of binding of the complex to the model duplex d(CGCAATTGCG)(2) possibly from the major groove with a slight preference for GC rich region. Additionally, the title complex promotes the cleavage of plasmid pBR322 DNA upon irradiation under aerobic conditions. (C) 2011 Elsevier B. V. All rights reserved.
• Synthesis, structure, DNA binding and photonuclease activity of a nickel(II) complex with a N,N′-Bis(salicylidene)-9-(3,4-diaminophenyl)acridine ligand
  作者：Mariappan Mariappan、Masahiko Suenaga、Abhik Mukhopadhyay、Bhaskar G. Maiya

  DOI：10.1016/j.ica.2012.04.016

  日期：2012.7
• DIAGNOSTIC DEVICES WITH MODIFIABLE HYDROPHOBIC SURFACES
  申请人：Siemens Healthcare Diagnostics Inc.

  公开号：US20170246627A1

  公开（公告）日：2017-08-31

  A diagnostic device 10 for screening for a target analyte in a sample is provided. The diagnostic device 10 comprises a substrate 12 and a hydrophobic material 20 disposed on the substrate. The hydrophobic material 20 is selected to be converted from the hydrophobic material 20 to a hydrophilic material 22 upon contact with a conversion component within or derived from a sample introduced to the device 10.
• [EN] DIAGNOSTIC DEVICES WITH MODIFIABLE HYDROPHOBIC SURFACES<br/>[FR] DISPOSITIFS DE DIAGNOSTIC À SURFACES HYDROPHOBES MODIFIABLES
  申请人：SIEMENS HEALTHCARE DIAGNOSTICS

  公开号：WO2016036658A1

  公开（公告）日：2016-03-10

  A diagnostic device 10 for screening for a target analyte in a sample is provided. The diagnostic device 10 comprises a substrate 12 and a hydrophobic material 20 disposed on the substrate. The hydrophobic material 20 is selected to be converted from the hydrophobic material 20 to a hydrophilic material 22 upon contact with a conversion component within or derived from a sample introduced to the device 10.