4-(2-pyridylazo)phenol | 7687-22-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(2-pyridylazo)phenol
• 英文别名: 4-[2-(Pyridin-2-yl)hydrazinylidene]cyclohexa-2,5-dien-1-one；4-(pyridin-2-yldiazenyl)phenol
• CAS: 7687-22-1
• 化学式: C₁₁H₉N₃O
• 分子量: 199.212
• InChiKey: YFRFEGAIERVYOL-UHFFFAOYSA-N

物化性质

• 沸点：
  398.9±22.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-pyridylazo)phenol 生成 4-(Pyridin-2-yl-hydrazono)-cyclohexa-2,5-dienone
  参考文献：
  名称：

  Pilipenko, A. T.; Savranskii, L. I.; Sheptun, V. L., Doklady Chemistry, 1987, vol. 293, p. 176 - 179

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯吡啶 在 硫酸 、 一水合肼 作用下， 以 水 为溶剂， 反应 8.5h， 生成 4-(2-pyridylazo)phenol
  参考文献：
  名称：

  Cytotoxicity of η-areneruthenium-based molecules to glioblastoma cells and their recognition by multidrug ABC transporters

  摘要：

  A new series of amphiphilic eta(6)-areneruthenium(II) compounds containing phenylazo ligands (group I: compounds la, 1b, 2a and 2b) and phenyloxadiazole ligands (group II: compounds 3a, 3b, 4a and 4b) were synthesized and characterized for their anti-glioblastoma activity. The effects of the amphiphilic eta(6)-areneruthenium(II) complexes on the viability of three human glioblastoma cell lines, U251, U87MG and T98G, were evaluated. The azo-derivative ruthenium complexes (group I) showed high cytotoxicity to all cell lines, whilst most oxadiazole-derivative complexes (group II) were less cytotoxic, except for compound 4a. The cationic complexes 2a, 2b and 4b were more cytotoxic than the neutral complexes. Compounds 2a and 2b caused a significant reduction in the percentage of cells in the G0/G1 phase, with concomitant increases in the G2/M phase and fragmented DNA in the T98G cell line. The eta(6)-areneruthenium(11) compounds were also tested in cell lines that overexpress the multidrug ABC transporters P-gp, MRP1 and ABCG2. Compounds 2b and 4a were substrates for the P-gp protein, with resistance indexes of 8.6 and 1.9, respectively. Compound 2b was also a substrate for ABCG2 and MRP1 proteins, with lower resistance indexes (1.8 and 1.6, respectively). The contribution of multidrug ABC transporters to the cytotoxicity of compound 2b in T98G cells was evidenced, since verapamil (a characteristic inhibitor of MRP1) increased the cytotoxicity of compound 2b at concentrations up to 20 mu mol L-1, whilst GP120918 and Ko143 (specific inhibitors of P-gp and ABCG2, respectively) had no significant effect. In addition, we showed that compound 2b interacts with glutathione (GSH), which could explain its cellular efflux by MRP1. Our results showed that the amphiphilic eta(6)-areneruthenium(II) complexes are promising anti-glioblastoma compounds, especially compound 2b, which was cytotoxic for all three cell lines, although it is transported by the three main multidrug ABC transporters. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.026

文献信息

• OSMIUM (II) ARENE AZO ANTI-CANCER COMPLEXES
  申请人：Fu Ying

  公开号：US20130040925A1

  公开（公告）日：2013-02-14

  The present invention relates to the use of certain osmium containing complexes such as cytotoxic agents particularly for the treatment of cancer. There is also provided novel osmium containing complexes, as well as pharmaceutical formulations comprising such complexes.

  本发明涉及使用某些含有钌的配合物，如细胞毒性药物，特别用于治疗癌症。还提供了新型含有钌的配合物，以及包括这些配合物的药物配方。
• Phenylazo-pyridine and Phenylazo-pyrazole Chlorido Ruthenium(II) Arene Complexes:  Arene Loss, Aquation, and Cancer Cell Cytotoxicity
  作者：Sarah J. Dougan、Michael Melchart、Abraha Habtemariam、Simon Parsons、Peter J. Sadler

  DOI：10.1021/ic061460h

  日期：2006.12.1

  decomposition of the complexes via hydrolysis and/or arene loss (t(1/2) = 9-21 h for azopyridine complexes, 310 K). The pKa* of the coordinated water in [(eta6-p-cym)Ru(azpyz-NMe2)OH2]2+ (13A) is 4.60, consistent with the increased acidity of the ruthenium center upon coordination to the azo ligand. None of the azpy complexes were cytotoxic toward A2780 human ovarian or A549 human lung cancer cells, but several

  钌（II）eta6-芳烃配合物，其中含有对苯异丙基（p-cym），四氢萘（thn），苯（bz）或联苯（bip）作为芳烃，苯基偶氮吡啶衍生物（C5H4NN：NC6H5R; R = H（azpy ），已合成作为N，N-螯合配体和氯化物作为配体的OH（azpy-OH），NMe2（azpy-NMe2））或苯基偶氮吡唑衍生物（NHC3H2NN：NC6H5NMe2（azpyz-NMe2））（1-16） 。由于在可见光区域发生的金属到配体的电荷转移Ru 4d6-pi *和配体内pi-> pi *的跃迁（eta = 5000-63 700 M-1 cm-1），所有络合物都显着着色。在[（eta6-p-cym）Ru（azpy）Cl] PF6（1）的晶体结构中，[（eta6-p-cym）Ru（azpy-NMe2Cl）Cl] PF6（5）和[（eta6- bip）Ru（azpy）Cl] PF6（4），相对较长的
• Ligand-centred redox activation of inert organoiridium anticancer catalysts
  作者：Wen-Ying Zhang、Samya Banerjee、George M. Hughes、Hannah E. Bridgewater、Ji-Inn Song、Ben G. Breeze、Guy J. Clarkson、James P. C. Coverdale、Carlos Sanchez-Cano、Fortuna Ponte、Emilia Sicilia、Peter J. Sadler

  DOI：10.1039/d0sc00897d

  日期：——

  Organometallic complexes with novel activation mechanisms are attractive anticancer drug candidates. Here, we show that half-sandwich iodido cyclopentadienyl iridium(III) azopyridine complexes exhibit potent antiproliferative activity towards cancer cells, in most cases more potent than cisplatin. Despite their inertness towards aquation, these iodido complexes can undergo redox activation by attack

  具有新颖激活机制的有机金属配合物是有吸引力的候选抗癌药物。在这里，我们发现半夹心碘化环戊二烯基铱（III）偶氮吡啶复合物对癌细胞表现出有效的抗增殖活性，在大多数情况下比顺铂更有效。尽管它们对水合呈惰性，但这些碘络合物可以通过攻击螯合的偶氮吡啶配体上丰富的细胞内三肽谷胱甘肽（GSH）来进行氧化还原活化，生成顺磁性中间体和羟基自由基，以及硫醇桥联的双核铱络合物，并释放还原的肼吡啶配体。DFT 计算提供了对这种激活机制的深入了解。GS -对偶氮键的攻击促进了碘化物被GS -取代，并且如果O 2在主要放能途径中作为电子受体存在，则导致GSSG和超氧化物的形成。这些碘配合物与 GSH 反应生成Ir-SG配合物，它是 GSH 氧化的催化剂。这些复合物促进人类肺癌细胞中活性氧（ROS）水平的升高。这种以配体为中心的显着激活机制与氧化还原反应相结合，为有机铱抗癌前药的设计增加了新的维度。
• Photoactive Platinum(II) Azopyridine Complexes ^†
  作者：Sarah J. Farley、Luca Salassa、Ana M. Pizarro、Peter J. Sadler

  DOI：10.1111/php.13405

  日期：2022.1

  groups. In complexes with substituted Ph-azpy ligands, σ-donation from NMe2 and OH/O– groups results in a redshift of the main absorption bands compared with unsubstituted Ph-azpy complexes. The diazido complexes are photoactive in solution upon irradiation with either UVA or visible light for R = H or NMe2, or UVA only when R = OH/O–. Intriguingly, the phenolate group of the latter complex undergoes

  铂 (II) 配合物含有强 π-受体N , N - 螯合配体 苯基偶氮吡啶 (Ph-azpy) [Pt( p -R-Ph-azpy)X 2 ], R = H, NMe 2或 OH, X = Cl或 N 3, 已经合成和表征，以探索单齿配体和苯基取代基对其吸收光谱和光活化的影响。时间相关的密度泛函理论计算表明，配合物具有低空未占轨道，对大多数配位键具有较强的 σ 反键特性。紫外可见吸收带主要被指定为以配体为中心或金属到配体的电荷转移跃迁，其中氯代和叠氮基的贡献很大。在具有取代的 Ph-azpy 配体的配合物中，来自 NMe 2和 OH/O的 σ-捐赠–与未取代的 Ph-azpy 配合物相比，基团导致主要吸收带的红移。对于 R = H 或 NMe 2，当用 UVA 或可见光照射时，二叠氮基配合物在溶液中具有光活性，或者仅当 R = OH/O -时才使用 UVA 。有趣的是，后一种配合物的酚盐基
• WO2007/101997
  申请人：——

  公开号：——

  公开（公告）日：——