1-(2-hydroxyphenylazo)-2-naphthol | 4866-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-hydroxyphenylazo)-2-naphthol
• 英文别名: 1-(2-hydroxyphenylazo)-2-hydroxynaphthalene；(2'-hydroxyphenylazo)-2-hydroxynaphthalene；1-[(2-hydroxyl)phenylazo]-2-naphthol；1-(2'-hydroxybenzeneazo)-2-naphthol；1-(2-hydroxyphenylazo)-2-napthol；2-hydroxyphenyl azo-2'-naphthol；1-[(2-hydroxyphenyl)diazenyl]naphthalen-2-ol
• CAS: 4866-98-2
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: QFHZPBSLCHTFBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyphenylazo)-2-naphthol 生成 (14E,14'E)-[8,8']spirobi(benzo[d]naphtho[1,2-h][1,3,6,7,2]dioxadiazasilonine)
  参考文献：
  名称：

  Chavan,S.N. et al., Indian Journal of Chemistry, 1975, vol. 13, p. 808 - 811

  摘要：

  DOI：
• 作为产物：
  描述：

  2-萘酚 在 五氯化磷 作用下， 生成 1-(2-hydroxyphenylazo)-2-naphthol
  参考文献：
  名称：

  Charrier; Ferreri, Gazzetta Chimica Italiana, 1911, vol. 41 II, p. 726

  摘要：

  DOI：

文献信息

• Identification of 1-(3,4-Dihydroxyphenylazo)-2-hydroxynaphthalene as the Product of Oxidation of 1-Phenylazo-2-hydroxynaphthalene (Sudan I, Solvent Yellow 14) by Rat Liver Microsomes
  作者：Marie Stiborová、Befekadu Asfaw、Eva Frei、Heinz H. Schmeiser、Manfred Wiessler

  DOI：10.1135/cccc19942727

  日期：——

  The carcinogenic azo dye 1-phenylazo-2-hydroxynaphthalene (Sudan I, Solvent Yellow 14) is oxidized by rat liver microsomes to a number of azo-containing metabolites. One of the products of hitherto unknown structure has been shown to be identical with 1-(3,4-dihydroxyphenylazo)-2-hydroxynaphthalene. The identification of this product completed the pattern of major products of Sudan I oxidation by microsomal cytochrome P-450.

  致癌的偶氮染料1-苯基偶氮-2-羟基萘（苏丹I，溶剂黄14）被大鼠肝微粒体氧化为多种含偶氮代谢物。迄今为止未知结构的其中一种产物已被证实与1-(3,4-二羟基苯基偶氮)-2-羟基萘相同。该产物的鉴定完成了微粒体细胞色素P-450对苏丹I氧化的主要产物的模式。
• Enhancement of anti-leukemic potential of 2-hydroxyphenyl-azo-2′-naphthol (HPAN) on MOLT-4 cells through conjugation with Cu(ii)
  作者：Tathagata Deb、Priya Kalyan Gopal、Durba Ganguly、Piyal Das、Mausumi Paul、Manju Bikash Saha、Santanu Paul、Saurabh Das

  DOI：10.1039/c3ra44765k

  日期：——

  A Cu(II) complex of 2-hydroxyphenyl-azo-2′-naphthol (HPAN) having the formula CuII(HPAN)2 was characterized by different techniques. When HPAN and CuII(HPAN)2 were incubated for 24 hours with human T-acute lymphoblastic leukemia (MOLT-4) cells, almost no activity was observed for HPAN while the complex was active. When incubated for 48 hours, HPAN showed cell death of ∼35% at a concentration of 40 μM while CuII(HPAN)2 was only slightly better than when incubated for 24 hours. Therefore, irrespective of incubation time, the anti-proliferative activity due to CuII(HPAN)2 was similar. However, increase in incubation time did show increased activity for HPAN. Anti-leukemic potential was confirmed by microscopic analysis of cell viability by trypan blue stain and MTT assay. The BrdU assay further confirmed proliferative effects of aqueous Cu(II)/HPAN and anti-proliferative effects of Cu(II)(HPAN)2. Propidium iodide staining of Cu(II)(HPAN)2-treated MOLT-4 cells confirmed apoptosis. Since amines formed as a consequence of reduction of the azo bond are reported to be cytotoxic, we performed an enzyme assay to understand the relative reduction of the azo bond in both compounds. Results suggest reduction of the azo bond was slightly higher for HPAN. DNA binding of CuII(HPAN)2 using fluorescence spectroscopy was compared with that of HPAN to determine the propensity of biological activity. The results being similar, binding of the compounds with DNA and the ease of reduction of the azo bond were not able to explain why CuII(HPAN)2 was better in preventing cell proliferation. The high anti-proliferative activity of CuII(HPAN)2 was attributed to increased cellular uptake. We designed experiments to support this hypothesis using independent approaches. In one, Cu(II) was identified in cell lysates using ferrocyanide, while, in another, CuII(HPAN)2 was detected using flow cytometry. We chose Cu(II) as the metal ion for this work because of its recognized involvement in cancer. Being essential for angiogenesis, it is found in increased levels in cancer cells. Interaction of Cu(II)(aq) with MOLT-4 cells confirmed this as a part of this study also. Hence, our objective was to see if molecules like HPAN that bind Cu(II) could lead to its role reversal, i.e. from supporting the growth of cancer cells to be able to destroy them as CuII(HPAN)2.

  一种 2-hydroxyphenyl-azo-2â²-naphthol (HPAN) 的 Cu(II) 复合物通过不同的技术进行了表征，其化学式为 CuII(HPAN)2。将 HPAN 和 CuII(HPAN)2 与人类 T 型急性淋巴细胞白血病（MOLT-4）细胞培养 24 小时后，几乎观察不到 HPAN 的活性，而复合物却具有活性。培养 48 小时后，当浓度为 40 ¼M 时，HPAN 的细胞死亡率为 35%，而 CuII(HPAN)2 的活性仅略高于培养 24 小时的结果。因此，无论培养时间长短，CuII（HPAN）2 的抗增殖活性都是相似的。然而，孵育时间的延长确实增加了 HPAN 的活性。通过胰蓝染色和 MTT 试验对细胞存活率进行显微分析，证实了抗白血病的潜力。BrdU测定进一步证实了Cu(II)/HPAN水溶液的增殖作用和Cu(II)(HPAN)2的抗增殖作用。Cu(II)(HPAN)2 处理过的 MOLT-4 细胞的碘化丙啶染色证实了细胞凋亡。据报道，偶氮键还原形成的胺具有细胞毒性，因此我们进行了酶测定，以了解这两种化合物中偶氮键的相对还原情况。结果表明，HPAN 的偶氮键还原程度略高。我们利用荧光光谱比较了 CuII(HPAN)2 与 HPAN 的 DNA 结合情况，以确定生物活性的倾向。结果相似，化合物与 DNA 的结合以及偶氮键还原的难易程度并不能解释为什么 CuII(HPAN)2 能更好地防止细胞增殖。CuII(HPAN)2 的高抗增殖活性归因于细胞摄取量的增加。我们设计了不同的实验来支持这一假设。其中一个实验使用亚铁氰化钾鉴定细胞裂解物中的 Cu(II)，而另一个实验则使用流式细胞仪检测 CuII(HPAN)2。我们选择 Cu(II)作为这项研究的金属离子，是因为它被公认与癌症有关。Cu(II)对血管生成至关重要，因此在癌细胞中的含量会增加。Cu(II)(aq) 与 MOLT-4 细胞的相互作用也证实了这一点。因此，我们的目标是研究 HPAN 等与 Cu(II) 结合的分子是否会导致 Cu(II) 的作用发生逆转，即从支持癌细胞生长转变为能够像 CuII(HPAN)2 一样摧毁癌细胞。
• Single-crystal-to-single-crystal transformation in hydrogen-bond-induced high-spin pseudopolymorphs from protonated cation salts with a π-extended spin crossover Fe(III) complex anion
  作者：Suguru Murata、Kazuyuki Takahashi、Takahiro Sakurai、Hitoshi Ohta

  DOI：10.1016/j.poly.2017.03.046

  日期：2017.11

  Abstract Novel pseudopolymorphic Hdabco compounds with an Fe(III) complex anion, (Hdabco)[Fe(aznp)2]·CH2Cl2 1 and (Hdabco)[Fe(aznp)2]·0.5H2O 2 [dabco = 1,4-diazabicyclo[2.2.2]octane, H2aznp = (2′-hydroxyphenylazo)-2-hydroxynaphthalene], were prepared and characterized. The magnetic susceptibility for 1 and 2 revealed that both complexes were in a high-spin (HS) state in the whole temperature range

  摘要具有Fe（III）配位阴离子（Hdabco）[Fe（aznp）2]·CH2Cl2 1和（Hdabco）[Fe（aznp）2]·0.5H2O 2的新型假多晶Hdabco化合物[dabco = 1,4-二氮杂双环制备并表征了[2.2.2]辛烷，H2aznp =（2'-羟基苯基偶氮）-2-羟基萘]。1和2的磁化率表明，两种配合物在整个温度范围内均处于高自旋（HS）状态，并且在40 K以下显示弱的铁磁相互作用。晶体结构分析表明，强的N–H⋯O氢键相互作用Hdabco阳离子与[Fe（aznp）2]阴离子之间的相互作用可能会导致配位结构发生扭曲，从而形成HS络合物，而[Fe（aznp）2]阴离子中π配体之间的π堆积相互作用以及Hdabco阳离子和[Fe（aznp）2]阴离子之间额外的C–H⋯N氢键相互作用构成了分子间相互作用的骨架结构，一维渠道。化合物1的热重分析表明水分子的吸附发生在二氯甲烷分子
• Synthesis, structure and biological evaluation of mixed ligand oxidovanadium(<scp>iv</scp>) complexes incorporating 2-(arylazo)phenolates
  作者：Sudhir Lima、Atanu Banerjee、Monalisa Mohanty、Gurunath Sahu、Chahat Kausar、Samir Kumar Patra、Eugenio Garribba、Werner Kaminsky、Rupam Dinda

  DOI：10.1039/c9nj01910c

  日期：——

  [VO(acac)2] was used as a metal precursor to synthesize a series of mixed ligand oxidovanadium(IV) complexes [VIVO(L1–4)(LNN)] (1–5) with tridentate ONO donor arylazo ligands (H2L1–4) (where H2L1 = 1-(2-hydroxyphenyl)diazenyl)naphthane-2-ol, H2L2 = 1-(2-hydroxy-4-methylphenyl)diazenyl)naphthane-2-ol, H2L3 = 1-(2-hydroxy-4-nitrophenyl)diazenyl)naphthane-2-ol and H2L4 = 1-(2-hydroxy-4-bromophenyl)di

  [VO（acac）2 ]用作金属前体与三齿ONO供体芳基偶氮合成一系列混合配体氧化钒（IV）络合物[V IV O（L 1-4）（L NN）]（1-5）配体（H 2 L 1-4）（其中H 2 L 1 = 1-（2-羟基苯基）二氮烯基）萘-2-醇，H 2 L 2 = 1-（2-羟基-4-甲基苯基）二氮烯基）萘烷-2-ol，H 2 L 3 = 1-（2-羟基-4-硝基苯基）二氮烯基）萘-2-醇和H 2 L 4＝ 1-（2-羟基-4-溴苯基）二氮烯基）萘-2-醇）以及辅助配体（L NN），即2,2'-联吡啶（bipy）或1,10-菲咯啉（phen）共配体。所有配合物均通过光谱，ESI-MS和X射线晶体学技术表征，显示出扭曲的八面体几何形状。分子结构显示在六配位的V IV N 3 O 3几何形状中存在钒基。该物质表现出在-1.29和-1.37 V之间的准可逆单电子转移E c 1/2值，而不可逆的单电子氧化峰在0
• Synthesis of New Metal Complex Derivatives Based on Azo, Naphthol and Pyrazole Moieties for Color Filter Pigments
  作者：Chang-Hun Seok、Jae-Yun Jaung、Jongwook Park

  DOI：10.1080/15421406.2010.495682

  日期：2010.10.8

  and Co based metal complex derivatives for new violet and red color filters were first synthesized by using naphthol and pyrazole groups as well as azo moiety. The UV-visible maximum values of Co(HPANT)2 and Cr(HPANT)2, the naphthol derivatives, were 560 and 561 nm respectively in solution state where both were violet colored solids. Co(HPAPMP)2 and Cr(HPAPMP)2, the pyrazole derivatives also showed

  首先通过使用萘酚和吡唑基团以及偶氮部分合成了四种用于新型紫色和红色滤色器的 Cr 和 Co 基金属络合物衍生物。萘酚衍生物 Co(HPANT)2 和 Cr(HPANT)2 的紫外可见最大值分别为 560 和 561 nm，在溶液状态下，两者都是紫色固体。Co(HPAPMP)2 和 Cr(HPAPMP)2，吡唑衍生物在溶液状态下也分别显示出 465 和 510 nm 的紫外可见最大值，表明为棕色和红色固体。与商业颜料相比，基于更高的摩尔消光系数值，所有这些化合物都表现出更好的清晰颜色。