2,2'-(2,6-吡啶二基)双[1-苯基-1H-苯并咪唑] | 1236181-38-6

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 2,2'-(2,6-吡啶二基)双[1-苯基-1H-苯并咪唑]
• 英文名称: 2,6-bis(1-phenylbenzimidazol-2-yl)pyridine
• 英文别名: bpbp；2,6-bis(2-(1-phenyl)benzimidazole)pyridine；2,6-Bis(1-phenyl-1H-benzoimidazole-2-yl)pyridine；1-phenyl-2-[6-(1-phenylbenzimidazol-2-yl)pyridin-2-yl]benzimidazole
• CAS: 1236181-38-6
• 化学式: C₃₁H₂₁N₅
• 分子量: 463.541
• InChiKey: ZQNUBJOJRJGFNU-UHFFFAOYSA-N

物化性质

• 沸点：
  745.0±70.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2'-(2,6-吡啶二基)双[1-苯基-1H-苯并咪唑] 、 cadmium(II) chloride 反应 0.5h， 以76%的产率得到[Cd(bpbp)Cl₂]
  参考文献：
  名称：

  Syntheses, crystal structure and luminescent properties of cadmium complexes based on 2,6-bis(1-phenylbenzimidazol-2-yl)pyridine

  摘要：

  Two cadmium complexes, Cd(bpbp)Cl-2 (complex 1) and [Cd(bpbp)(2)](ClO4)(2) (complex 2), based on 2,6-bis(1-phenylbenzimidazol-2-yl)pyridine (bpbp), were synthesized and characterized by X-ray single crystal structure analyses. For complex 1: crystal system, monoclinic, space group, C2/c, a = 27.427(3) angstrom, b = 13.4495(15) angstrom, c = 14.8381(17) angstrom, beta = 106.635(2)degrees, V = 5244.4(10) angstrom(3), Z = 8. It is a neutral complex. The Cd(II) ion distorted trigonal bipyramidal geometry is five-coordinated by three nitrogen atoms from ligand (bpbp) and two chlorine ions. For complex 2: crystal system, triclinic, space group, P-1, a = 13.4791(15) angstrom, b = 13.8506(16) angstrom, c = 16.5839(19) angstrom, alpha = 94.202(2)degrees, beta = 106.948(2)degrees, beta = 94.872(2)degrees, V = 2935.3(6) angstrom(3), Z = 2. It is an ionic complex. The Cd(II) ion octahedral geometry is six-coordinated by six nitrogen atoms from two ligand (bpbp). Both complexes emit blue luminescence with emission peaks at 420 and 430 nm in solid state and with emission peaks at 415 and 425 nm in DMF solution. In complex 1 absorption spectra, there is not only the free ligand absorption peak at 310 nm, but also shows strong Cd-Cl charge transfer peak at 350 nm in DMF solution. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2012.06.039
• 作为产物：
  描述：

  6-(羟基甲基)吡啶甲醛 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 、 甲乙醚 、 水 为溶剂， 反应 74.0h， 生成 2,2'-(2,6-吡啶二基)双[1-苯基-1H-苯并咪唑]
  参考文献：
  名称：

  选择性氧化铁催化苯甲醇和烯丙醇的氧化

  摘要：

  已经开发了用过氧化氢方便且选择性地氧化醇以产生醛和酮的方法。使用原位生成的氯化铁络合物[Fe（L3）2 Cl n ] [n = 0–1，L3 = 6-（N-苯基苯并咪唑基）-2-吡啶羧酸]，可以高收率和优异的选择性获得醛和酮。在室温下短时间反应后。

  DOI：

  10.1002/adsc.201100210

文献信息

• Highly efficient oxidation of diphenylmethane to benzophenone employing a novel ruthenium catalyst with tert-butylhydroperoxide under mild conditions
  作者：Sheng-Gui Liu、Xian-Tai Zhou、Hong-Bing Ji

  DOI：10.1016/j.catcom.2013.03.031

  日期：2013.7

  tested in the selective oxidation of diphenylmethane to benzophenone utilizing tert-butylhydroperoxide as the terminal oxidant. The influence of various reaction parameters such as temperature, catalyst amount and nature of solvent on the activity and selectivity was evaluated. Diphenylmethane was converted with 94% conversion and 100% selectivity to benzophenone under the optimized reaction conditions

  已合成钌络合物Ru（bpbp）（pydic）（bpbp = 2,6-双（1-苯基苯并咪唑-2-基），pydic =吡啶-2,6-二羧酸）并在二苯甲烷的选择性氧化中进行了测试用叔丁基过氧化氢作为末端氧化剂制得二苯甲酮。评估了温度，催化剂用量和溶剂性质等各种反应参数对活性和选择性的影响。在优化的反应条件下，二苯甲烷以94％的转化率和100％的选择性转化为二苯甲酮，其中催化剂的周转数（TON）达到94,000。此外，提出了通过氧化还原钌物种的合理反应机理。
• Zinc(ii) complexes containing bis-benzimidazole derivatives as a new class of apoptosis inducers that trigger DNA damage-mediated p53 phosphorylation in cancer cells
  作者：Shenggui Liu、Wenqiang Cao、Lianling Yu、Wenjie Zheng、Linlin Li、Cundong Fan、Tianfeng Chen

  DOI：10.1039/c3dt33077j

  日期：——

  In the present study, two zinc(II) complexes containing bis-benzimidazole derivatives, Zn(bpbp)Cl2 (1) and [Zn(bpbp)2](ClO4)2·CH3CH2OH·H2O (2) (bpbp = 2,6-bis(1-phenyl-1H-benzo[d]imidazol-2-yl)pyridine), have been designed, synthesized and evaluated for their in vitro anticancer activities. The underlying molecular mechanisms through which they caused the cancer cell death were also elucidated. The complexes were identified as potent antiproliferative agents against a panel of five human cancer cell lines by comparing with cisplatin. Complex 2 demonstrated dose-dependent growth inhibition on MCF-7 human breast carcinoma cells with IC50 at 2.9 μM. Despite this potency, the complexes possessed great selectivity between human cancer cells and normal cells. Induction of apoptosis in MCF-7 cells by complex 2 was evidenced by accumulation of sub-G1 cell population, DNA fragmentation and nuclear condensation. Further investigation on intracellular mechanisms revealed that complex 2 was able to induce p53-dependent apoptosis in cancer cells by triggering DNA damage. On the basis of this evidence, we suggest that Zn(II) complexes containing bis-benzimidazole derivatives may be candidates for further evaluation as chemotherapeutic agents for human cancers.

  本研究设计、合成了两种含有双苯并咪唑衍生物的锌（II）配合物，即 Zn(bpbp)Cl2 (1) 和 [Zn(bpbp)2](ClO4)2-CH3C H-H2O (2)（bpbp = 2,6-双(1-苯基-1H-苯并[d]咪唑-2-基)吡啶），并对其体外抗癌活性进行了评估。同时还阐明了它们导致癌细胞死亡的基本分子机制。通过与顺铂比较，发现这些复合物对五种人类癌细胞株具有强效抗增殖作用。复合物 2 对 MCF-7 人类乳腺癌细胞具有剂量依赖性生长抑制作用，IC50 为 2.9 μM。尽管具有这种效力，但复合物在人类癌细胞和正常细胞之间具有很大的选择性。复合物 2 对 MCF-7 细胞凋亡的诱导作用表现为亚 G1 细胞群的积累、DNA 断裂和核凝结。对细胞内机制的进一步研究表明，复合物 2 能够通过引发 DNA 损伤来诱导癌细胞发生 p53 依赖性凋亡。基于这些证据，我们认为含有双苯并咪唑衍生物的 Zn（II）复合物可作为人类癌症化疗药物进行进一步评估。
• 一种可用于药物检测的配合物的合成方法
  申请人：湖北大学

  公开号：CN107954986B

  公开（公告）日：2019-10-11

  本发明涉及一种新型可用于药物检测的配合物的合成方法，具体涉及一种含Pb的配合物Pb(bpbp)3(NO3)2，其中bpbp代表的是2,6‑二(2‑(1‑苯基)苯并咪唑)吡啶。本发明也涉及了此配合物的晶体结构。本发明的制备方法简便，毒性小，快速，产量高。相较于此类配体配合物的晶体培养的常规方法，本发明的合成用到的溶剂为水和甲醇，三天就可以得到大量晶体。通过荧光分析法，测试目标产物和牛血清白蛋白(BSA)的相互作用的荧光光谱。BSA的荧光猝灭现象表明，此配合物与牛血清白蛋白有较强的相互作用，进而推断该物质可应用到生物药物检测方面。
• 一种钌配合物及其制备方法和应用
  申请人：岭南师范学院

  公开号：CN107445998A

  公开（公告）日：2017-12-08

  本发明涉及一种钌配合物及其制备方法和应用，所述钌配合物的结构如式（I）、（II）或（III）所示：式（I） 式（II） 式（III）。本发明提供的钌配合物在低于80℃的温度条件下可催化过氧化氢氧化2‑羟烷基苯并咪唑制备2‑羰基苯并咪唑，催化活性强，催化反应产率高、条件温和、污染少。
• METHOD OF MAKING BENZAZOLES
  申请人：Shi Jianmin

  公开号：US20130172570A1

  公开（公告）日：2013-07-04

  This present invention provides a method of making benzazoles comprising a process of making aryl or alkyl benzazoles from corresponding aryl acid chlorides or alkyl acid chlorides without applying hazard condensing agent. The benzazole compounds described in this invention have following formula I: Wherein: n is an integer of from 3 to 8; Z is O, NR or S; and R and R′ are individually hydrogen; alkyl of from 1 to 24 carbon atoms, for example, propyl, t-butyl, heptyl, and the like; aryl or hetero-atom substituted aryl of from 5 to 20 carbon atoms, for example, phenyl and naphthyl, furyl, thienyl, pyridyl, quinolinyl and other heterocyclic systems; or halo such as chloro, fluoro, bromo, cyano; or atoms necessary to complete a fused aromatic ring; and B is a linkage unit consisting of alkyl, aryl, substituted alkyl, or substituted aryl which conjugately or unconjugately connects the multiple benzazoles together.

  本发明提供了一种制备苯并咪唑的方法，包括从相应的芳基酸氯化物或烷基酸氯化物中制备芳基或烷基苯并咪唑的过程，而无需应用危险的缩合剂。本发明中描述的苯并咪唑化合物具有以下式I： 其中： n是从3到8的整数； Z是O、NR或S； R和R'分别为氢、1至24个碳原子的烷基（例如丙基、叔丁基、庚基等）、5至20个碳原子的芳基或杂原子取代的芳基（例如苯基和萘基、呋喃基、噻吩基、吡啶基、喹啉基和其他杂环系统）或卤素，例如氯、氟、溴、氰；或必要的原子以完成融合芳环；且 B是连接多个苯并咪唑的共轭或非共轭的烷基、芳基、取代烷基或取代芳基的连接单元。