4'-(3-chlorophenyl)-2,2':6',2''-terpyridine | 1259925-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4'-(3-chlorophenyl)-2,2':6',2''-terpyridine
• 英文别名: 4'-(3-Chlorophenyl)-2,2':6',2''-terpyridine；4-(3-chlorophenyl)-2,6-dipyridin-2-ylpyridine
• CAS: 1259925-94-4
• 化学式: C₂₁H₁₄ClN₃
• 分子量: 343.815
• InChiKey: QECQQFRGEXDIBK-UHFFFAOYSA-N

物化性质

• 沸点：
  499.8±40.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4'-(3-chlorophenyl)-2,2':6',2''-terpyridine 、 palladium dichloride 以 N,N-二甲基甲酰胺 为溶剂， 以84 %的产率得到
  参考文献：
  名称：

  合成、表征和抗癌特性：一系列高选择性钯(II)取代三联吡啶配合物

  摘要：

  通过氯化钯(II)与10个4′-(取代苯基)-2,2′:6′,2′反应合成了10种新的钯(II)配合物[PdCl(L 1 − 10 ) ] Cl '-三联吡啶配体，含氢( L 1 )、对羟基( L 2 )、间羟基( L 3 )、邻羟基( L 4 )、甲基( L 5 )、苯基( L 6 )、氟( L ) 7 )、氯 ( L 8 )、溴 ( L 9 ) 或碘 ( L 10 )）。它们的结构通过FT-IR、 1 H NMR、元素分析和/或单晶X射线衍射分析证实。他们的体外基于五种细胞系研究了抗癌活性，包括四种癌细胞系（A549、Eca-109、Bel-7402、MCF-7）和一种正常细胞系（HL-7702）。结果表明，这些复合物对癌细胞具有很强的杀伤作用，但对正常细胞的增殖抑制作用较弱，这表明它们对癌细胞系的增殖具有高度的抑制选择性。流式细胞术表征表明，这些复合物主要在G0/G1期影响细胞增殖，并诱导细胞晚期凋亡。通过

  DOI：

  10.1016/j.jinorgbio.2023.112219
• 作为产物：
  描述：

  2-乙酰基吡啶 、 3-氯苯甲醛 在 ammonium hydroxide 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 4'-(3-chlorophenyl)-2,2':6',2''-terpyridine
  参考文献：
  名称：

  司巴沙星药物与氮供体配体的铜（II）配合物的细胞毒性，抗菌，DNA相互作用和超氧化物歧化酶活性

  摘要：

  合成并表征了新型中性单核铜（II）与氟喹诺酮类抗菌药，司帕沙星和氮供体杂环配体的配合物。已测试了该复合物对五种不同微生物的抗菌功效，并显示出多种生物活性。使用粘度滴定和吸收滴定技术研究了复合物与鲱鱼精子（HS）DNA的相互作用。结果表明，该复合物通过插入模式与DNA结合并且具有相当高的DNA结合常数。DNA裂解研究表明，与金属盐和标准药物相比，该复合物具有更好的裂解能力。所有复合物均显示出良好的细胞毒性活性，LC 50值为4.89至11.94μgmL -1。配合物还表现出类似于SOD的活性，其IC 50值为0.717至1.848μM。

  DOI：

  10.1016/j.saa.2012.11.045

文献信息

• Antibacterial, DNA interaction and superoxide dismutase activity of drug based copper(II) coordination compounds
  作者：Mohan N. Patel、Promise A. Dosi、Bhupesh S. Bhatt

  DOI：10.1016/j.poly.2010.08.037

  日期：2010.11

  inhibitory activities than the reference antibacterial quinolone drugs against Gram(+ve) and Gram(−ve) bacteria. The coordination compounds can act as catalysts for the dismutation of superoxide anion radicals (O2·-). The detection of the rate constant of the reaction of superoxide ion with nitro blue tetrazolium (NBT) is inhibited by superoxide dismutase (SOD). The interaction of the complex with DNA was

  合成了新颖的中性单核铜（II）与喹诺酮类抗菌药物环丙沙星在叔吡啶的氮供体杂环配体存在下的配合物，并通过元素分析，反射光谱，红外光谱和质谱表征。评价了新合成化合物的抗菌活性，并将其与其理化性质相关联。结果表明，与参比抗菌喹诺酮类药物相比，所测试的化合物对革兰氏（+ ve）和革兰氏（-ve）细菌表现出更好的抑制活性。配位化合物可充当超氧化物阴离子自由基（O2·-）。超氧化物歧化酶（SOD）抑制了超氧离子与硝基蓝四唑（NBT）反应速率常数的检测。使用粘度，吸收滴定和DNA熔解温度技术研究了复合物与DNA的相互作用。结果表明，该复合物以插入模式与DNA结合，并且它们具有相当高的DNA结合常数。DNA裂解研究表明，与金属盐和标准药物相比，该复合物具有更好的裂解能力。
• Effect of solvent on the crystal structures of copper(II) complexes based on 4′-(4-methoxyphenyl)-2,2′:6′,2″-terpyridine and 4′-(3-chlorophenyl)-2,2′:6′,2″-terpyridine
  作者：W. W. Fu、Q. W. Cheng、H. Y. Wang、F. Z. R. He、Y. Liu、F. X. Zhang

  DOI：10.1134/s1070328417080024

  日期：2017.8

  Four homoleptic copper(II) complexes, [Cu(Meophtpy)2](ClO4)2 (Meophtpy = 4′-(4-methoxylphenyl)- 2,2′:6′,2″-terpyridine) (I), [Cu(Meophtpy)2](ClO4)2 · 2H2O (II), [Cu2(m-Clphtpy)4](ClO4)4 (m-ClPhtpy = 4′-(3-chlorophenyl)-2,2′:6′,2″-terpyridine) (III), and [Cu2(m-ClPhtpy)4](ClO4)4 (IV) have been synthesized by hydrothermal methods and characterized by IR, elemental analysis and single crystal X-ray diffraction

  四种均化的铜（II）配合物[Cu（Meophtpy）2 ]（ClO 4）2（Meophtpy = 4'-（4-甲氧基苯基）-2,2'：6'，2''-叔吡啶）（I），[ Cu（Meophtpy）2 ]（ClO 4）2 ·2H 2 O（II），[Cu 2（m -Clphtpy）4 ]（ClO 4）4（m -ClPhtpy = 4'-（3-氯苯基）-2， 2'：6'，2''-叔吡啶）（III）和[Cu 2（m -ClPhtpy）4 ]（ClO 4）4（IV）已通过水热法合成，并通过IR，元素分析和单晶X射线衍射进行了表征（CIF文件CCDC号963375（I），885457（II），963377（III）和963376（IV））。复合物II是I的多晶型物，而复合物IV是III的多晶型物。所有这些配合物都是用95％乙醇溶液或50％乙醇溶液获得的，并且明显发现了控制结晶的溶剂。在所有配合物中，吡啶环
• Copper(II) complexes with norfloxacin and neutral terpyridines: Cytotoxic, antibacterial, superoxide dismutase and DNA-interaction approach
  作者：Mohan N. Patel、Hardik N. Joshi、Chintan R. Patel

  DOI：10.1016/j.poly.2012.03.050

  日期：2012.6

  Cu(II) complexes of the type [Cu(NFL)(L-n)Cl] (L-n = substituted terpyridines, NFL = norfloxacin) were synthesised and characterized. Antibacterial activity was assayed against selective Gram((+ve)) and Gram((-ve)) microorganisms using the double dilution technique. The binding behavior of the complexes toward Herring Sperm (HS) DNA was determined using absorption titration and hydrodynamic measurements, whereas the cleavage efficacy of the complexes toward pUC19 DNA was determined by the gel electrophoresis technique. The brine shrimp bioassay was carried out to study the in vitro cytotoxic properties of the synthesized metal complexes. The superoxide dismutase (SOD) like activity of the complexes was measured using an NBT/NADH/PMS system and is expressed in term of the concentration of complex which terminates the formation of formazan by 50% (IC50 value). The IC50 values were observed to be in the range 0.653-1.344 mu M. (C) 2012 Elsevier Ltd. All rights reserved.
• DNA-binding and cleavage activity of polypyridyl ruthenium(II) complexes
  作者：Mohan N. Patel、Deepen S. Gandhi、Pradhuman A. Parmar、Hardik N. Joshi

  DOI：10.1080/00958972.2012.685728

  日期：2012.6.10

  Polypyridyl ruthenium(II) complexes [Ru-II(3-bptpy)(dmphen)Cl]ClO4 (1), [Ru-II(3-cptpy) (dmphen) Cl] ClO4 (2), [Ru-II(2-tptpy)(dmphen) Cl]ClO4 (3), and [Ru-II(9-atpy)(dmphen)Cl]ClO4 (4) where 3-bptpy 4'-(3-bromophenyl)-2,2':6',2 ''-terpyridine, 3-cptpy 4'-(3-chlorophenyl)-2,2':6',2 ''-terpyridine, 2-tptpy 4'-(2-thiophenyl)-2,2':6',2 ''-terpyridine, 9-atpy 4'-(9-anthryl)-2,2':6',2 ''-terpyridine, dmphen 2,9-dimethyl-1,10-phenanthroline} have been synthesized and characterized. The DNA-binding properties of the complexes with Herring Sperm DNA have been investigated by absorption titration and viscosity measurements. The ability of complexes to break the pUC19 DNA has been checked by gel electrophoresis. The experimental results suggest that all the complexes bind DNA via partial intercalation. The results also show that the order of DNA-binding affinities of the complexes is 4 < 3 < 2 < 1, confirming that planarity of the ligand in a complex is very important for DNA-binding.
• Syntheses and crystal structures of [Fe(m-NO2phtpy)2](ClO4)2 and [Fe(m-Clphtpy)2](ClO4)2 (m-NO2phtpy = 4′-(3-nitrophenyl)-2,2′:6′,2″-terpyridine and m-Clphtpy = 4′-(3-chlorophenyl)-2,2′:6′,2″-terpyridine)
  作者：W. -W. Fu、F. -X. Zhang、D. -Z. Kuang

  DOI：10.1134/s002247661405014x

  日期：2014.9

  Two iron compounds [Fe(m-NO(2)phtpy)(2)](ClO4)(2) 1 and [Fe(m-Clphtpy)(2)](ClO4)(2) 2 are synthesized and their structures are determined by single crystal X-ray diffraction. Crystal data for 1 are: orthorhombic, space group Pcca, a = 25.471(4) , b = 10.8182(18) , c = 14.682(2) , Z = 4. Crystal data for 2 are: orthorhombic, space group Pnna, a = 14.521(2) , b = 23.980(4) , c = 23.142(4) , and Z = 8. The iron atoms are coordinated by six N atoms from two terpyridines in both compounds. These two compounds are all linked by hydrogen bonds with C as donor and O as acceptor into a 3D network for 1 and a 2D network for 2. If viewed along the c direction in 1 and the a direction in 2, both compounds show the ordered figure with terpyridine overlapped as a square and the phenyl rings overlapped as a rectangle or a square.