6-hydroxydipyrido[3,2-a:2',3'-c]phenazine | 873928-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 6-hydroxydipyrido[3,2-a:2',3'-c]phenazine
• 英文别名: 6-hydroxy-dipyrido[a,c]phenazine；hdppz
• CAS: 873928-03-1
• 化学式: C₁₈H₁₀N₄O
• 分子量: 298.304
• InChiKey: UORPEBCBROABLG-UHFFFAOYSA-N

物化性质

• 沸点：
  638.2±35.0 °C(Predicted)
• 密度：
  1.512±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  23.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.79
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(2-氯乙基)哌啶 、 6-hydroxydipyrido[3,2-a:2',3'-c]phenazine 在 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以60.7%的产率得到10-(2-(piperidin-1-yl)ethoxy)dipyrido[3,2-a:2′,3′c]phenazine
  参考文献：
  名称：

  Novel ruthenium(ii) polypyridyl complexes as G-quadruplex stabilisers and telomerase inhibitors

  摘要：

  两种新型钌聚吡啶配合物，Ru[(bpy)2(pedppz)]2+ (1) 和 Ru[(bpy)2(pemitatp)]2+ (2) (bpy = 2′2-联吡啶，pdeppz = 10- (2-(哌啶-1-基)乙氧基)二吡啶并[3,2-a:2′,3′-c]吩嗪,pemitatp = 5-甲氧基-1-(2-(哌啶-1-基)乙基) -isatino[1,2-b]-1,4,8,9-四氮杂苯并菲），具有柔性链的大平面π离域芳香系统已被合成和表征。正如预期的那样，这些复合物通过诱导和稳定 G-四链体结构来抑制端粒酶。

  DOI：

  10.1039/c3dt53547a
• 作为产物：
  描述：

  2,3-二氨基苯酚 、 1,10-邻二氮杂菲-5,6-二酮 以 乙醇 为溶剂， 以60 %的产率得到6-hydroxydipyrido[3,2-a:2',3'-c]phenazine
  参考文献：
  名称：

  钌 (II) 聚吡啶复合物 [Ru(bpy)2(10-OH-dppz)]2+ 对映体对 RNA 三链聚 (U*AU) 的结合和稳定作用

  摘要：

  两个新的手性钌 (II) 配合物，Δ-[Ru (bpy) 2 (10-OH-dppz)] 2+ (Δ- 1; bpy = 2,2ʹ-bipyridine, 10-OH-dppz = 10-hydroxyl- dipyrido [3,2- a :2',3'- c ]phenazine) 和 Λ-[Ru (bpy) 2 (10-OH-dppz)] 2+ (Λ- 1 ), 已在此合成并表征工作。已经研究了两种对映体与 RNA 三链聚 (U*AU) 的结合特性 [在文本中，破折号 (−) 表示 Watson-Crick 碱基配对，星号 (*) 表示 Hoogsteen 碱基配对]。吸收光谱和荧光光谱分析表明，对映体 Λ- 1的结合常数向三链体的方向略小于对映体 Δ- 1的方向，这进一步得到了粘度实验的支持。粘度实验表明，虽然两种对映异构体被嵌入到三链体中，但 Δ-对映异构体是比 Λ-对映异构体更好

  DOI：

  10.1016/j.dyepig.2023.111377

文献信息

• Substituent effects on the interactions of ruthenium(II) polypyridyl complexes [Ru(bpy)2(6-R-dppz)]2+ (R = hydroxy and fluorine) with the RNA triplex poly(rU)·poly(rA) × poly(rU)
  作者：Xuanbin Wang、Xiaohua Liu、Lifeng Tan

  DOI：10.1016/j.poly.2021.115196

  日期：2021.7

  Two new ruthenium(II) polypyridyl complexes, [Ru(bpy)2(6-OH-dppz)]2+ (Ru1, bpy = 2,2′-bipyridine, 6-OH-dppz = 6-hydroxydipyrido[3,2-a:2′,3′-c]phenazine) and [Ru(bpy)2(6-F-dppz)]2+ (Ru2, 6-F-dppz = 6-fluorodipyrido[3,2-a:2′,3′-c]-phenazine), have been synthesized and characterized in this work. The interactions of Ru1 and Ru2 with the RNA triplex poly(rU)·poly(rA) × poly(rU) have been investigated by

  两个新的钌（II）聚吡啶基络合物[Ru（bpy）2（6-OH-dppz）] 2+（Ru 1，bpy = 2,2'-联吡啶，6-OH-dppz = 6-羟基双吡啶[3， 2-一个：2'，3'- ç ]吩嗪）和[吡啶钌2（6-F-dppz）] 2+（RU 2，6-F-dppz = 6-fluorodipyrido [3,2-一个：2'，3'- c ]-吩嗪），已经合成并且在这项工作中表征。通过光谱学和黏度技术研究了Ru 1和Ru 2与RNA三链体poly（rU）·poly（rA）×poly（rU）的相互作用。光谱滴定和粘度实验表明Ru的结合方式1和Ru 2到三链体是插入的，对Ru 2的结合亲和力大于对Ru 1的结合亲和力。荧光滴定表明，Ru 2与Ru 1不同，可以充当三元组的“分子光开关”。此外，热变性实验表明Ru 1和Ru 2使三链体的Hoogsteen碱基配对链（第三链）稳定，没有显着差异
• [Ru(phen)₂podppz]²⁺ significantly inhibits glioblastoma growth <i>in vitro</i> and <i>vivo</i> with fewer side-effects than cisplatin
  作者：Ruihao Li、Yabin Ma、Xiaochun Hu、Wenjing Wu、Xuewen Wu、Chunyan Dong、Shuo Shi、Yun Lin

  DOI：10.1039/d0dt01877e

  日期：——

  Ru1 could most effectively inhibit tumor growth and avoid any detectable side-effects compared with other ruthenium(ii) complexes and cisplatin, demonstrating its potential to be an exciting new drug candidate for glioblastoma treatment.

  Ru1相较于其他钌（II）配合物和顺铂，能够最有效地抑制肿瘤生长并避免任何可检测的副作用，显示出它作为一种令人兴奋的新药候选物治疗胶质母细胞瘤的潜力。
• Ruthenium(ii) complexes of 6-hydroxydipyrido[3,2-a:2′,3′-c]phenazine: self-association, and concentration-dependent acid–base and DNA-binding properties
  作者：Mei-Jiao Han、Yan-Min Chen、Ke-Zhi Wang

  DOI：10.1039/b711759k

  日期：——

  6-Hydroxydipyrido[3,2-a:2′,3′-c]phenazine (hdppz) and its ruthenium(II) complexes of [Ru(bpy)2(hdppz)]X2 (bpy = 2,2′-bipyridine and X = ClO4−, PF6− and Cl−) have been synthesized and characterized. The ion association (self aggregation of the complex cation, and ion pairing) behaviors have been studied in both aqueous and nonaqueous (MeCN) media by UV-visible spectrophotometric measurements. The c

  6-羟基双吡啶并[3,2- a：2′，3′- c ]吩嗪 （高清视频）及其 钌（II）[Ru（bpy）2（hdppz）] X 2（py = 2,2'-联吡啶和X = CLO 4 -，PF 6 -和氯−）已合成并表征。已经研究了在水性和非水性（离子交换）中的离子缔合（复合阳离子的自聚集和离子对）行为。机械化）媒体 紫外线可见分光光度法测量。浓度依赖的基态和激发态酸碱性质高氯酸盐 已通过pH研究复合物 分光光度滴定。小牛胸腺DNA结合 的属性 高氯酸盐 复合体已被研究 紫外线可见 和发光 滴定，稳态发射猝灭通过 [Fe（CN）6 ] 4−，脱氧核糖核酸 与...的竞争结合 溴化乙锭， 脱氧核糖核酸熔融实验和粘度测量。结果表明，离子缔合性能显着由抗衡离子和浓度的影响与CLO的影响4 -是最突出的。水溶液中的离子缔合高氯酸盐 络合物通过超过0.2个pH单位的差异适度影响络合物的酸度电离常数，但会影响
• Excited-State Interaction of Red and Green Perylene Diimides with Luminescent Ru(II) Polypyridine Complex
  作者：Rajeev K. Dubey、Marja Niemi、Kimmo Kaunisto、Kati Stranius、Alexander Efimov、Nikolai V. Tkachenko、Helge Lemmetyinen

  DOI：10.1021/ic400474b

  日期：2013.9.3

  Three new perylene diimide (PDI)-based ligands have been synthesized by the covalent attachment of dipyrido[a,c]phenazine moiety to one of the bay positions of PDI, while the second position has been substituted with either a 4-tert-butylphenoxy or a 7 ET pyrrolidinyl group to obtain two types of chromophores, Ph-PDI and Py-PDI, respectively, with distinct properties. In the case of Py-PDI, the resultant 1,7- and 1,6-regioisoMers have been successfully separated. by column chromatography and characterized by H-1 NMR spectroscopy. The ligands have been employed to prepare donor acceptor-based ensembles incorporating the covalently linked PDI and Ru(II) polypyridine complex as the acting chromophores. A comprehensive study of excited state photodynamics.of the ensembles has been performed by means, of electrochemical and steady state and time, resolved spectroscopic methods. Although, in all the three ensembles, the photoexcitation of either chromophore resulted in a long-lived triplet excited state of PDI ((PDI)-P-3) as the final excited state, the photochemical reactions leading to the triplet states were found to be essentially different for the two types of the ensembles. In the case of the Ph-PDI-based ensemble, the excitation of either chromophore leads to the electron transfer from the Ru(II) complex to Ph-PDI, whereas for the Py-PDI-based ensembles, the electron transfer is observed in the opposite direction and only when the Ru(II) complex is excited. The difference in the behavior was rationalized based on electrochemical study of the compounds, which has shown that the Ph-PDI chromophore is a better electron acceptor and the Py-PDI chromophores are relatively better electron donors. This study shows a chemical approach to control the photoreactions in PDI-based dichromophoric ensembles including the possibility to switch the direction of the photoinduced electron transfer.