bis[4′-(4-methyl-2,2′-bipyridyl)]-1,16-hexadecane | 1269508-96-4

• 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: bis[4′-(4-methyl-2,2′-bipyridyl)]-1,16-hexadecane
• 英文别名: bis[4-(4′-methyl-(2,2′-bipyridyl))]-1,16-hexadecane；bis[4(4′-methyl-2,2′-bipyridyl)]-1,16-hexadecane；2-(4-Methylpyridin-2-yl)-4-[16-[2-(4-methylpyridin-2-yl)pyridin-4-yl]hexadecyl]pyridine
• CAS: 1269508-96-4
• 化学式: C₃₈H₅₀N₄
• 分子量: 562.842
• InChiKey: KMKDQZOLRUIKIB-UHFFFAOYSA-N

物化性质

• 沸点：
  689.8±50.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.6
• 重原子数：
  42
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 Ir(tpy)Cl₃ 、 bis[4′-(4-methyl-2,2′-bipyridyl)]-1,16-hexadecane 以 乙二醇 为溶剂， 反应 18.0h， 生成 [iridium(III)(2,2′:6′,2″-terpyridine)(bis[4(4′-methyl-2,2′-bipyridyl)]-1,16-hexadecane)](hexafluorophosphate)4
  参考文献：
  名称：

  Chlorido-containing ruthenium(ii) and iridium(iii) complexes as antimicrobial agents

  摘要：

  一系列含有易替换氯配体的聚吡啶铬(II)和铱(III)复合物[{M(tpy)Cl}2{μ-bbn}]2/4+ {Cl-Mbbn; 其中 M = Ru 或 Ir; tpy = 2,2′:6′,2′′-三吡啶; bbn = 二[4(4′-甲基-2,2′-联吡啶)]-1,n-烷烃 (n = 7, 12 或 16)}已被合成，并考察了其作为抗微生物剂的潜力。已确定一系列金属复合物对四种细菌株的最小抑制浓度（MIC）和最小杀菌浓度（MBC）——革兰阳性金黄色葡萄球菌（S. aureus）和耐甲氧西林金黄色葡萄球菌（MRSA），以及革兰阴性大肠杆菌（E. coli）和铜绿假单胞菌（P. aeruginosa）。所有铬复合物均表现出高度活性和杀菌效果。特别是，Cl-Rubb12复合物在对所有细菌细胞系的MIC值方面表现出优异的活性，针对革兰阳性细菌的MIC值为1 μg mL−1，对E. coli和P. aeruginosa的MIC值分别为2 μg mL−1和8 μg mL−1。相应的铱(III)复合物在MIC值方面也表现出显著的抗微生物活性；然而，令人惊讶的是，铱复合物是抑菌的，而不是杀菌的。惰性的铱(III)复合物[{Ir(phen)2}2{μ-bb12}]6+ {其中 phen = 1,10-菲啰啉}未表现出任何抗微生物活性，表明它无法穿过细菌膜。单核模型复合物[Ir(tpy)(Me2bpy)Cl]Cl2（其中 Me2bpy = 4,4′-二甲基-2,2′-联吡啶）被发现水合非常迅速，相应水合复合物中铱键合水的pKa值被测定为6.0。这表明二核复合物[Ir(tpy)Cl}2{μ-bbn}]4+迅速水合并脱质子，作为4+带电羟基物种进入细菌细胞。

  DOI：

  10.1039/c3dt32775b

文献信息

• Multinuclear ruthenium(<scp>ii</scp>) complexes as anticancer agents
  作者：Anil K. Gorle、Alaina J. Ammit、Lynne Wallace、F. Richard Keene、J. Grant Collins

  DOI：10.1039/c4nj00545g

  日期：——

  series of dinuclear ruthenium(II) complexes that contain labile chlorido ligands, [Ru(tpy)Cl}2μ-bbn}]2+ designated Cl-Rubbn; tpy = 2,2′:6′,2′′-terpyridine, bbn = bis[4(4′-methyl-2,2′-bipyridyl)]-1,n-alkane (n = 7, 10, 12, 14 or 16)} and derivatives containing nitro substituents on the tpy ligand and/or secondary amines within the bbn linking chain have been synthesised and their potential as anticancer

  一系列的双核钌（的II含有不稳定chlorido配体）配合物，[茹（TPY）氯} 2 μ-BB Ñ }] 2+ 指定CL-Rubb Ñ ; tpy = 2,2'：6'，2''-吡啶，bb n =双[4（4'-甲基-2,2'-联吡啶基）]-1，n-烷烃（n = 7，10，12 ，14或16）}和在bb n连接链内的tpy配体和/或仲胺上含有硝基取代基的衍生物已经合成，并研究了它们作为抗癌剂的潜力。一些Cl-Rubb n菌种对MCF-7和MDA-MB-231乳腺癌细胞系表现出良好的抗癌活性，其中Cl-Rubb 12复合物的活性是顺铂的四倍。Cl-Rubb 12的tpy配体上包含硝基取代基导致抗癌活性大大降低。胺基团结合到连接配体中并没有增加Cl-Rubb n配合物的抗癌活性。Cl-Rubb n络合物和在连接链中含有胺基的络合物以大约相同的速率水合，在120分钟内水合50％。相比之下，tp
• Dinuclear ruthenium(<scp>ii</scp>) complexes containing one inert metal centre and one coordinatively-labile metal centre: syntheses and biological activities
  作者：Xin Li、Kirsten Heimann、Fangfei Li、Jeffrey M. Warner、F. Richard Keene、J. Grant Collins

  DOI：10.1039/c5dt04885k

  日期：——

  non-symmetric dinuclear polypyridylruthenium(II) complexes (Rubbn-Cl) that contain one inert metal centre and one coordinatively-labile metal centre, linked by the bis[4(4′-methyl-2,2′-bipyridyl)]-1,n-alkane ligand (“bbn” for n = 7, 12 and 16), have been synthesised and their potential as antimicrobial agents examined. The minimum inhibitory concentrations (MIC) of the ruthenium(II) complexes were determined

  一系列不对称的双核聚吡啶钌（II）配合物（Rubb n -Cl），包含一个惰性金属中心和一个配位不稳定的金属中心，并通过双[4（4'-甲基-2,2'-联吡啶）连接）]-1，正构烷烃配体（n = 7、12和16时为“ bb n ” ），已经研究了它们作为抗菌剂的潜力。确定了钌（II）配合物对四种细菌的最低抑制浓度（MIC）-革兰氏阳性金黄色葡萄球菌（S. aureus）和耐甲氧西林的金黄色葡萄球菌（MRSA）以及革兰氏阴性大肠杆菌（大肠杆菌）和铜绿假单胞菌（P.aeruginosa）。Rubb n -Cl复合物表现出良好的抗菌活性，其中Rubb 12 -Cl是针对革兰氏阳性和革兰氏阴性菌株最活跃的复合物。有趣的是，发现Rubb 7 -Cl对大肠杆菌的活性分别比对金黄色葡萄球菌和MRSA的活性高八倍和十六倍。研究了Rubb n -Cl复合物对三种真核细胞系（两种肾细胞系（BHK和HEK-293
• Oligonuclear polypyridylruthenium(ii) complexes incorporating flexible polar and non-polar bridges: synthesis, DNA-binding and cytotoxicity
  作者：Yanyan Mulyana、Daniel K. Weber、Damian P. Buck、Cherie A. Motti、J. Grant Collins、F. Richard Keene

  DOI：10.1039/c0dt01250e

  日期：——

  The paper reports the synthesis and characterisation of a series of flexible di-bidentate bridging ligands in which two 4-methyl-2,2′-bipyridine groups are linked at the 4′-position by polymethylene (bbn), linear polyether (bbOn) or linear alkylamine (bbNn) chains of varying length (n). The enantiomers (ΔΔ/ΛΛ) of the rac forms of the ruthenium(II) dinuclear complexes incorporating these ligands – i.e. [Ru(phen)2}2(μ-BL)]4+ (phen = 1,10-phenanthroline; BL = bbn, bbOn or bbNn) – have been isolated by reaction of Δ- or Λ-[Ru(phen)2(py)2]2+ (py = pyridine) with the respective bridging ligands. Mononuclear species - in which only one of the bidentate moieties of the bridging ligand is coordinated – have also been isolated, as well as trinuclear and tetranuclear species involving the bb7 bridge. Fluorescence displacement studies of the DNA-binding of the dinuclear complexes containing the bbOn and bbNn bridges generally revealed a lower affinity than their bbn analogues for an oligonucleotide containing a single bulge site; the mononuclear complexes showed a lower affinity - and the trinuclear and tetranuclear complexes a higher affinity – than the dinuclear species, revealing an interesting interplay of lipophilicity, electrostatics and size in the complex/nucleic acid interaction. Cytotoxicity studies of these complexes against a murine leukaemia cell line revealed that the presence of the polyether or polyamine links in the chain lowered the cytotoxicity compared with their polymethylene analogues, and that the bb7-bridged trinuclear and tetranuclear complexes showed considerably enhanced cytotoxicity compared with the dinuclear Rubb7 analogue.

  该论文报道了一系列柔性二齿桥连配体的合成和表征，其中两个4-甲基-2,2'-联吡啶基团通过聚亚甲基（bbn）、线性聚醚（bbOn）在4'位连接或不同长度 (n) 的线性烷基胺 (bbNn) 链。包含这些配体的钌(II)双核配合物的外消旋形式的对映体 (ΔΔ/ΛΛ) – 即 [Ru(phen)2}2(μ-BL)]4+ (phen = 1,10-菲咯啉； BL = bbn、bbOn 或 bbNn) – 通过 Δ- 或 Λ-[Ru(phen)2(py)2]2+ (py = 吡啶) 与各自的桥接配体反应分离。单核物种（其中仅桥配体的二齿部分之一被配位）以及涉及 bb7 桥的三核和四核物种也已被分离出来。含有 bbOn 和 bbNn 桥的双核复合物的 DNA 结合的荧光置换研究通常表明，与含有单个凸出位点的寡核苷酸相比，它们的 bbn 类似物具有较低的亲和力；与双核物质相比，单核复合物表现出较低的亲和力，而三核和四核复合物则表现出更高的亲和力，揭示了复合物/核酸相互作用中亲脂性、静电和大小之间有趣的相互作用。这些复合物针对小鼠白血病细胞系的细胞毒性研究表明，与聚亚甲基类似物相比，链中聚醚或多胺连接的存在降低了细胞毒性，并且与双核 Rubb7 类似物。
• Tri- and tetra-nuclear polypyridyl ruthenium(<scp>ii</scp>) complexes as antimicrobial agents
  作者：Anil K. Gorle、Marshall Feterl、Jeffrey M. Warner、Lynne Wallace、F. Richard Keene、J. Grant Collins

  DOI：10.1039/c4dt02139h

  日期：——

  A series of inert tri- and tetra-nuclear polypyridylruthenium(II) complexes that are linked by the bis[4(4′-methyl-2,2′-bipyridyl)]-1,n-alkane ligand (“bbn” for n = 10, 12 and 16) have been synthesised and their potential as antimicrobial agents examined. Due to the modular nature of the synthesis of the oligonuclear complexes, it was possible to make both linear and non-linear tetranuclear ruthenium

  一系列惰性的三和四核聚吡啶基钌（II）配合物，它们通过双[4（4'-甲基-2,2'-联吡啶基）]-1，n-烷烃配体（“ bb n ” n = 10、12和16）已被合成，并检验了它们作为抗微生物剂的潜力。由于寡核配合物合成的模块性质，可以同时制备线性和非线性四核钌物种。确定了钌（II）配合物对四种细菌的最低抑菌浓度（MIC）-革兰氏阳性金黄色葡萄球菌（S. aureus）和耐甲氧西林的金黄色葡萄球菌（MRSA）和革兰氏阴性大肠杆菌（E. coli）和铜绿假单胞菌（P. aeruginosa）。为了了解相对的抗菌活性，确定了钌配合物选择的细胞吸收率和水-辛醇分配系数（log  P）。尽管基于log P，三核复合物是最亲脂的 并显示最大的细胞摄取，线性四核复合物通常更具活性，对革兰氏阳性细菌的MIC值<1μM。类似地，尽管非线性四核复合物的亲脂性稍强，并且被细菌吸收的程度更大，但它们的活性始终
• Chlorido-containing ruthenium(ii) and iridium(iii) complexes as antimicrobial agents
  作者：Mallesh Pandrala、Fangfei Li、Marshall Feterl、Yanyan Mulyana、Jeffrey M. Warner、Lynne Wallace、F. Richard Keene、J. Grant Collins

  DOI：10.1039/c3dt32775b

  日期：——

  A series of polypyridyl-ruthenium(II) and -iridium(III) complexes that contain labile chlorido ligands, [M(tpy)Cl}2μ-bbn}]2/4+ Cl-Mbbn; where M = Ru or Ir; tpy = 2,2′:6′,2′′-terpyridine; and bbn = bis[4(4′-methyl-2,2′-bipyridyl)]-1,n-alkane (n = 7, 12 or 16)} have been synthesised and their potential as antimicrobial agents examined. The minimum inhibitory concentrations (MIC) and minimum bactericidal concentrations (MBC) of the series of metal complexes against four strains of bacteria – Gram positive Staphylococcus aureus (S. aureus) and methicillin-resistant S. aureus (MRSA), and Gram negative Escherichia coli (E. coli) and Pseudomonas aeruginosa (P. aeruginosa) – have been determined. All the ruthenium complexes were highly active and bactericidal. In particular, the Cl-Rubb12 complex showed excellent activity against all bacterial cell lines with MIC values of 1 μg mL−1 against the Gram positive bacteria and 2 and 8 μg mL−1 against E. coli and P. aeruginosa, respectively. The corresponding iridium(III) complexes also showed significant antimicrobial activity in terms of MIC values; however and surprisingly, the iridium complexes were bacteriostatic rather than bactericidal. The inert iridium(III) complex, [Ir(phen)2}2μ-bb12}]6+ where phen = 1,10-phenanthroline) exhibited no antimicrobial activity, suggesting that it could not cross the bacterial membrane. The mononuclear model complex, [Ir(tpy)(Me2bpy)Cl]Cl2 (where Me2bpy = 4,4′-dimethyl-2,2′-bipyridine), was found to aquate very rapidly, with the pKa of the iridium-bound water in the corresponding aqua complex determined to be 6.0. This suggests the dinuclear complexes [Ir(tpy)Cl}2μ-bbn}]4+ aquate and deprotonate rapidly and enter the bacterial cells as 4+ charged hydroxo species.

  一系列含有易替换氯配体的聚吡啶铬(II)和铱(III)复合物[M(tpy)Cl}2μ-bbn}]2/4+ Cl-Mbbn; 其中 M = Ru 或 Ir; tpy = 2,2′:6′,2′′-三吡啶; bbn = 二[4(4′-甲基-2,2′-联吡啶)]-1,n-烷烃 (n = 7, 12 或 16)}已被合成，并考察了其作为抗微生物剂的潜力。已确定一系列金属复合物对四种细菌株的最小抑制浓度（MIC）和最小杀菌浓度（MBC）——革兰阳性金黄色葡萄球菌（S. aureus）和耐甲氧西林金黄色葡萄球菌（MRSA），以及革兰阴性大肠杆菌（E. coli）和铜绿假单胞菌（P. aeruginosa）。所有铬复合物均表现出高度活性和杀菌效果。特别是，Cl-Rubb12复合物在对所有细菌细胞系的MIC值方面表现出优异的活性，针对革兰阳性细菌的MIC值为1 μg mL−1，对E. coli和P. aeruginosa的MIC值分别为2 μg mL−1和8 μg mL−1。相应的铱(III)复合物在MIC值方面也表现出显著的抗微生物活性；然而，令人惊讶的是，铱复合物是抑菌的，而不是杀菌的。惰性的铱(III)复合物[Ir(phen)2}2μ-bb12}]6+ 其中 phen = 1,10-菲啰啉}未表现出任何抗微生物活性，表明它无法穿过细菌膜。单核模型复合物[Ir(tpy)(Me2bpy)Cl]Cl2（其中 Me2bpy = 4,4′-二甲基-2,2′-联吡啶）被发现水合非常迅速，相应水合复合物中铱键合水的pKa值被测定为6.0。这表明二核复合物[Ir(tpy)Cl}2μ-bbn}]4+迅速水合并脱质子，作为4+带电羟基物种进入细菌细胞。