4'-(1H-benzimidazol-2-yl)-2,2':,6',2''-terpyridine | 1211970-90-9

• 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'-(1H-benzimidazol-2-yl)-2,2':,6',2''-terpyridine
• 英文别名: 4'-(1H-benzimidazol-2-yl)-2,2':6',2''-terpyridine；4'-benzimidazolylterpyridine；benzimidazolylterpyridine；Bitpy；2-(2,6-dipyridin-2-ylpyridin-4-yl)-1H-benzimidazole
• CAS: 1211970-90-9
• 化学式: C₂₂H₁₅N₅
• 分子量: 349.395
• InChiKey: SBRDESOHZOWYBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4'-(1H-benzimidazol-2-yl)-2,2':,6',2''-terpyridine 在 LiCl 、 N(CH₂CH₃)3 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 生成 [Ru(II)(OH2)(4'-(1H-benzimidazol-2-yl)-2,2':6',2''-terpyridine)(2,2'-bipyridyl)](2+)
  参考文献：
  名称：

  Ruthenium(ii) [3 + 2 + 1] mixed ligand complexes: substituent effect on photolability, photooxidation of bases, photocytotoxicity and photonuclease activity

  摘要：

  已经合成并表征了二价钌的混合配体络合物[Ru(itpy)(bpy)Cl]ClO4、[Ru(itpy)(phen)Cl]ClO4、[Ru(bitpy)(bpy)Cl]ClO4和[Ru(bitpy)(phen)Cl]ClO4。复合物3也进行了晶体学表征。这些复合物表现出Ru–Cl键的光解特性。在440 nm光照下，在核苷和核苷酸存在的情况下，复合物与核苷或核苷酸交换氯离子。Ru–Cl键的光解性依赖于三齿tpy配体中取代基的性质。在核苷或核苷酸的存在下，这些复合物的光分解还会产生8-氧鸟苷，这是由于复合物的激发态对鸟苷的氧化。这四个复合物表现出光核酸酶特性，在440 nm光照下能够切割质粒DNA。这些复合物在光解条件下对NIH 3T3细胞表现出毒性。

  DOI：

  10.1039/c2dt30260h
• 作为产物：
  描述：

  2-乙酰基吡啶 、 苯并咪唑-2-甲醛 在 ammonium acetate 、 溶剂黄146 作用下， 以82%的产率得到4'-(1H-benzimidazol-2-yl)-2,2':,6',2''-terpyridine
  参考文献：
  名称：

  Synthesis, characterization and DNA binding studies of new ruthenium(II)bisterpyridine complexes

  摘要：

  Two new ruthenium(II) complexes, [Ru(itpy)(2)](PF6)(2), 1 and [Ru(bitpy)(2)](PF6)(2) 2, were synthesized and characterized by ESI-Mass, UV-Visible, H-1 NMF, fluorescence spectroscopy and cyclic voltammetry. Complex 1 has been characterized crystallographically. Interaction of these complexes with CT-DNA has been studied using absorption and CD spectra. Absorption spectral titration and CD spectral measurements show that complex 1 binds with DNA through intercalation. Complex 2 on the other hand shows dual mode of binding to DNA, groove binding as well as intercalation. Photo nuclease activity of these complexes has been studied using agarose gel electrophoresis and both the complexes have been shown to exhibit photonuclease activity. However, complex 1 has been found to show higher DNA cleaving efficiency compared to complex 2. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.008

文献信息

• A new platinum(<scp>ii</scp>) complex for bioimaging applications
  作者：Verasundaram M. Manikandamathavan、Natarajan Duraipandy、Manikantan S. Kiran、Vaidyanathan G. Vaidyanathan、Balachandran U. Nair

  DOI：10.1039/c5ra00002e

  日期：——

  A new Pt(ii) complex bearing terpyridine derivative exhibit specificity towards nuclear DNA. The staining ability has been explored in cell imaging as well as in gel electrophoresis an alternative to highly mutagenic ethidium bromide.

  一种带有三吡啶衍生物的新型 Pt (II) 配合物表现出对核DNA的特异性。该染色能力已经在细胞成像和凝胶电泳中得到探索，作为高度致突变性溴乙酸乙酯的替代品。
• Copper(II) complexes of terpyridine derivatives: A footstep towards development of antiproliferative agent for breast cancer
  作者：Subramaniyam Rajalakshmi、Thomas Weyhermüller、Murugan Dinesh、Balachandran Unni Nair

  DOI：10.1016/j.jinorgbio.2012.08.010

  日期：2012.12

  complexes have been found to exhibit cytotoxic effects against cancerous cell lines. Complex 2 which has lower IC50, was found to be a potent antiproliferative agent against MCF-7 cells and was able to induce mitochondrial-mediated and caspase-dependent apoptosis with increase in G0/G1 and subsequent arrest in the S phase, in cell cycle progression. Based on this study, it is hypothesized that 2 may be

  带有叔吡啶基共轭物的两种铜（II）配合物[Cu（mepypy）（dmp）]（NO 3）2（1）和[Cu（bitpy）（dmp）]（NO 3）2（2） dmp代表甲氧基苄基联吡啶，苯并咪唑基联吡啶和二甲基菲咯啉。配合物1也已经在结晶学上进行了表征。已经发现两种复合物都可插入地结合CT-DNA。使用凝胶电泳已经分析了这些复合物引起DNA切割的能力。1号和2号复合体已经发现引起DNA的水解裂解。已经测试了这两种复合物对癌细胞和非癌细胞系的细胞毒性。对非癌细胞系复合物2显示出非常低的毒性。另一方面，已经发现两种复合物均表现出针对癌细胞系的细胞毒性作用。已发现具有较低IC 50的复合物2是针对MCF-7细胞的有效抗增殖剂，并能够诱导线粒体介导的胱天蛋白酶依赖性细胞凋亡，并导致G 0 / G 1增加，并随后停在S期，在细胞周期进程中。根据这项研究，假设2 作为人癌症的化学预防和化学治疗剂，可能是进一步评估的合适人选。
• Synthesis, spectral characterization, protein binding and cytotoxic evaluation of new cobalt(II) and cobalt(III) complexes containing benzimidazolylterpyridine as ligand
  作者：Ramasamy Indumathy、Pathinathan Senthilrajkapoor、Giriraj Kalaiarasi、Gopal Sathyaraj、Varadarajan Uma

  DOI：10.1080/00958972.2022.2141116

  日期：2022.12.17

  Abstract Two new six-coordinate cobalt(II) [Co(bitpy)2]Cl2 (1) and cobalt(III) [Co(bitpy)2](ClO4)3 (2) complexes containing benzimidazolylterpyridine (bitpy) ligand have been synthesized and characterized using spectroscopic and electrochemical techniques. The g‖ and g⊥ values in the EPR spectrum for 1 were 2.215 and 2.012, respectively, and clearly authenticated the formation of stable octahedral

  摘要 两个新的六配位钴(II) [Co(bitpy) 2 ]Cl 2 ( 1 ) 和钴(III) [Co(bitpy) 2 ](ClO 4 ) 3 ( 2 ) 配合物含有苯并咪唑三联吡啶(bitpy)配体。使用光谱和电化学技术合成和表征。1的 EPR 光谱中的g ‖和g ⊥值分别为 2.215 和 2.012，清楚地证实了稳定的八面体低自旋 Co(II) 子午异构体复合物的形成。同样，1 H NMR 谱图2揭示了低自旋及其抗磁性。已经研究了配合物与牛血清白蛋白 (BSA) 的相互作用，并揭示钴配合物通过遵循静态猝灭机制来猝灭本征荧光。MTT 法用于检查2对人乳腺癌细胞 (MCF-7) 和人宫颈癌细胞 (HeLa) 的抗癌潜力。2的 IC 50值在癌细胞中低于 7 µM，在非癌细胞（人胚肾细胞）中高于 100 µM，表明复合物对癌细胞具有特异性。此外， 2引起的形态变化通过 AO-EB（吖啶橙-溴化乙锭）和
• DNA condensation by copper(II) complexes and their anti-proliferative effect on cancerous and normal fibroblast cells
  作者：Subramaniyam Rajalakshmi、Manikantan Syamala Kiran、Balachandran Unni Nair

  DOI：10.1016/j.ejmech.2014.04.064

  日期：2014.6

  In our search towards copper(II) based anticancer compounds, copper(II) complexes [Cu(bitpy)2](ClO4)21, [Cu(bitpy)(phen)](NO3)22 and [Cu(bitpy)(NO3)](NO3) 3 were synthesized and characterized. All the three complexes contain the tridentate ligand bitpy, which bears biologically relevant benzimidazolyl head group, as one of the ligands. Because of the presence of the planar benzimidazolyl group in the bitpy ligand, the complexes exhibited intercalative mode of binding with DNA. The DNA binding constant, K(b), for complexes 1, 2 and 3 were determined to be (1.84 ± 0.32) × 10(4), (1.83 ± 0.57) × 10(4) and (1.87 ± 0.21) × 10(4) M(-1) respectively. All the three complexes possessed DNA condensing ability. The DNA condensing ability of the complexes was in the order 2 > 1 > 3. The DNA condensation induced by these three complexes was found to be reversed in the presence of 1 M NaCl. In vitro cytotoxicity of three complexes was tested against osteosarcoma MG63 cell line as well as normal fibroblast NIH3T3 cell line by MTT reduction assay. Complexes 1 and 2 were found to be highly toxic towards MG63 than NIH3T3 cell line and both these complexes brought about cell death in the MG-63 cell line due to apoptosis. Whereas, complex 3 exhibited almost equal toxic effect towards both MG63 and NIH3T3 cell lines. Based on the fact that both complexes 1 and 2 brought about reversible condensation of DNA and induced apoptosis in osteosarcoma MG-63 cell line, it is hypothesized that they might possess potential pharmaceutical applications.