3-(pyridin-2-yl)dipyrido[3,2-a:2’,3’-c]phenazine | 945975-87-1

• 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: 3-(pyridin-2-yl)dipyrido[3,2-a:2’,3’-c]phenazine
• 英文别名: 6-(2-pyridyl)-dipyrido-[3,2-a:2',3'-c]-phenazine；3-(pyrid-2'-yl)dipyrido[3,2-a:2':3'-c]phenazine；6-(2-pyridyl)dipyrido[3,2-a:2',3'-c]phenazine；pydppz；3-(Pyridin-2-yl)dipyrido[3,2-a:2',3'-c]phenazine；6-pyridin-2-ylquinoxalino[2,3-f][1,10]phenanthroline
• CAS: 945975-87-1
• 化学式: C₂₃H₁₃N₅
• 分子量: 359.39
• InChiKey: VCISBHJFHOBFAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(pyridin-2-yl)dipyrido[3,2-a:2’,3’-c]phenazine 、 iron(II) chloride 以 甲醇 为溶剂， 反应 0.5h， 以90%的产率得到[Fe(3-(pyridin-2-yl)dipyrido[3,2-a:2’,3’-c]phenazine)₂]Cl₂
  参考文献：
  名称：

  Polypyridyl iron(II) complexes showing remarkable photocytotoxicity in visible light

  摘要：

  通过配位体B的铁(II)配合物，即N,N,N捐赠体2-(2-吡啶基)-1,10-菲啰啉（1中的pyphen）和3-(吡啶-2-基)双吡啶[3,2-a:2',3'-c]苯嗪（2中的pydppz），制备并表征了[Fe(B)2]Cl2（1和2）。它们在水相DMF中为1:2电解质。这些顺磁性配合物在DMF中显示出近570 nm的金属-配体电荷转移带。由于平面菲啰啉基团的存在，这些配合物与小牛胸腺DNA的结合常数(Kb)约为106 M−1，表明其具有显著的插层DNA结合能力。配合物2在永生化的人角质形成细胞HaCaT和乳腺癌细胞系MCF-7中表现出显著的光细胞毒性，在可见光（400-700 nm）下的IC50值分别为0.08和13 μM。配合物2在HaCaT细胞中仅显示出轻微的暗毒性，但在MCF-7癌细胞中则无毒性。光诱导的细胞损伤通过活性氧物质的生成遵循凋亡途径，DCFDA测定表明了这一点。

  DOI：

  10.1007/s12039-015-0815-0

文献信息

• Photocytotoxic Oxidovanadium(IV) Complexes of Polypyridyl Ligands Showing DNA‐Cleavage Activity in Near‐IR Light
  作者：Samya Banerjee、Akhtar Hussain、Puja Prasad、Imran Khan、Bhabatosh Banik、Paturu Kondaiah、Akhil R. Chakravarty

  DOI：10.1002/ejic.201200344

  日期：2012.8

  104 to 1.1 x 106 M1. The complexes show poor chemical nuclease activity in the dark and exhibit significant DNA-photocleaving activity in near-IR light of 705 and 785 nm forming .OH radicals. Complexes 2-4 show remarkable photocytotoxicity in HeLa cancer cells. FACS analysis of the HeLa cells treated with complex 4 shows cell death as highlighted by the sub G1 peak. Propidium iodide staining data indicate

  氧化钒 (IV) 配合物 VO(pyphen)(L)]Cl2 (1, 2) 和 VO(pydppz)(L)]Cl2 (3, 4)，其中 L 是 1,10-菲咯啉（phen 在 1 和 3）制备并表征了双吡啶并3,2-a:2',3'-c]吩嗪（2和4中的dppz）。VO(pyphen)(phen)](ClO4)2 (1a) 的晶体结构显示六配位的 VN5O 几何结构，其中多吡啶配体以经向方式结合，而 phen 配体显示出螯合结合模式与N-供体位点反式到氧化氧钒基。复合物在 DMF 中显示 720-750 nm 内的 dd 带。单电子顺磁复合物是 DMF 中的 1:2 电解质。在 DMF/0.1 M TBAP 中，复合物在 -0.85 V 与 SCE 附近表现出不可逆的 VIV/VIII 氧化还原响应。该复合物与小牛胸腺 (ct) DNA 结合，Kb 值在 7.5 x 104 到 1.1 x 106
• Photo-induced DNA cleavage activity and remarkable photocytotoxicity of lanthanide(iii) complexes of a polypyridyl ligand
  作者：Akhtar Hussain、Sudarshan Gadadhar、Tridib K. Goswami、Anjali A. Karande、Akhil R. Chakravarty

  DOI：10.1039/c1dt11400j

  日期：——

  photocleavage activity and photocytotoxicity studied. The crystal structure of complex 2 displays a GdO6N3 coordination. The pydppz complexes 3–5 show an electronic spectral band at ∼390 nm in DMF. The La(III) complexes are diamagnetic, while the Gd(III) complexes are paramagnetic with seven unpaired electrons. The molar conductivity data suggest 1 : 1 electrolytic nature of the complexes in aqueous DMF. They

  稀土（III） 配合物[Ln（吡啶）（acac）2（NO 3）]（1，2），[Ln（pydppz）（acac）2（NO 3）]（3，4），并[La（pydppz）（anacac）2（NO 3）]（5）其中Ln为La（III）（在1，3，5）和d（III）（在2，4），pyphen是6-（2-吡啶基）-1,10-菲咯啉， pydppz 是 6-（2-吡啶基）-二吡啶并[3,2- a：2'，3'- c ]吩嗪，anacac是 蒽基乙酰丙酮酸酯 和 acac 是 乙酰丙酮制备，表征并研究了它们的DNA光切割活性和光细胞毒性。配合物2的晶体结构显示GdO 6 N 3协调。这pydppz配合物3-5显示出在390 nm处的电子光谱带DMF。这La（III） 络合物是抗磁性的，而 d（III）络合物是顺磁性的，带有七个不成对的电子。摩尔电导率数据表明配合物在水溶液中具有1：1的电解性质DMF。它们是小牛胸腺DNA的狂热结合剂，K
• Marked Differences in Light-Switch Behavior of Ru(II) Complexes Possessing a Tridentate DNA Intercalating Ligand
  作者：Yao Liu、Richard Hammitt、Daniel A. Lutterman、Randolph P. Thummel、Claudia Turro

  DOI：10.1021/ic700484j

  日期：2007.7.1

  The tridentate ligand 3-(pyrid-2'-yl)dipyrido[3,2-a:2',3'-c]phenazine (pydppz) has been prepared in two steps by elaboration of 2-(pyrid-2'-yl)-1,10-phenanthroline. Both homoleptic [Ru(pydppz)(2)](2+) and heteroleptic [Ru(tpy)(pydppz)](2+) (tpy = 2,2';6',2' '-terpyridine) complexes have been prepared and characterized by H-1 NMR. The absorption and emission spectra are consistent with low-lying MLCT excited states, which are typical of Ru(II) complexes. Femtosecond transient absorption measurements show that that the (MLCT)-M-3 excited state of the heteroleptic complex [Ru(tpy)(pydppz)](2+) (tau approximate to 5 ns) is longer-lived than that of the homoleptic complex [Ru(pydppz)(2)](2+) (tau = 2.4 ns) and that these lifetimes are significantly longer than that of the (MLCT)-M-3 state of the parent complex [Ru(tpy)(2)](2+) (tau = 120 ps). These differences are explained by the lower-energy (MLCT)-M-3 excited state present in [Ru(tpy)(pydppz)](2+) and [Ru(pydppz)(2)](2+) compared to [Ru(tpy)(2)](2+), resulting in less deactivation of the former through the ligand-field state(s). DFT and TDDFT calculations are consistent with this explanation. [Ru(tpy)(pydppz)](2+) and [Ru(pydppz)(2)](2+) bind to DNA through the intercalation of the pydppz ligand; however, only the heteroleptic complex exhibits luminescence enhancement in the presence of DNA. The difference in the photophysical behavior of the complexes is explained by the inability of [Ru(pydppz)(2)](2+) to intercalate both pydppz ligands, such that one pydppz always remains exposed to the solvent. DNA photocleavage is observed for [Ru(tpy)(pydppz)](2+) in air, but not for [Ru(pydppz)(2)](2+). The DNA damage likely proceeds through the production of small amounts of O-1(2) by the longer-lived complex. Although both complexes possess the intercalating pydppz ligand, they exhibit different photophysical properties in the presence of DNA.
• Photo-induced anticancer activity of polypyridyl platinum(II) complexes
  作者：Basudev Maity、Sudarshan Gadadhar、Tridib K. Goswami、Anjali A. Karande、Akhil R. Chakravarty

  DOI：10.1016/j.ejmech.2012.09.025

  日期：2012.11

  Polypyridyl platinum(II) complexes (1-5), viz., [Pt(pyphen)Cl]Cl (1), [Pt(pyphen)(C CFc)]Cl (2), [Pt(pydppz)Cl]Cl (3), [Pt(pydppz)(C CPh)]Cl (4) and [Pt(pydppz)(C CFc)]Cl (5), where pyphen is 6-(2-pyridyl)-1,10-phenanthroline, pydppz is 6-(2-pyridyl)-dipyrido-[3,2-a:2',3'-c]-phenazine, FcC CH is ferrocenyl acetylene and PhC CH is phenyl acetylene, were synthesized, characterized and their DNA binding and photocytotoxic properties studied. The complexes showed strong binding affinity to calf-thymus DNA giving K-app of similar to 10(6)-10(7) M-1. Complexes 4 and 5 showed dual mode of binding to ct-DNA. The pydppz complexes 3-5 having a photoactive phenazine moiety showed photocytotoxicity in HeLa and MCF-7 cells in UV-A light of 365 nm with apoptotic cell death as evidenced from the acridine orange/ethidium bromide dual staining and the FACS data. (C) 2012 Elsevier Masson SAS. All rights reserved.