2-(N-salicylideneaminomethyl)benzimidazole | 104992-04-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(N-salicylideneaminomethyl)benzimidazole
• 英文别名: (benzimidazol-2-ylmethyl)salicylideneamine；N-(benzimidazol-2-ymethyl)salicylideneimine；Hsal-ambmz；6-({[(1H-Benzimidazol-2-yl)methyl]amino}methylidene)cyclohexa-2,4-dien-1-one；2-(1H-benzimidazol-2-ylmethyliminomethyl)phenol
• CAS: 104992-04-3
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: LLOFTSLVDSQRBO-UHFFFAOYSA-N

物化性质

• 沸点：
  505.2±35.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  61.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(N-salicylideneaminomethyl)benzimidazole 以 水 为溶剂， 生成 2-(aminomethyl)benzimidazole dihydrochloride 、 水杨醛
  参考文献：
  名称：

  Dash, Anadi; Panda, Debaraj; Dash, Bhaskar R., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1986, vol. 25, # 2, p. 141 - 146

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(aminomethyl)benzimidazole dihydrochloride 、 水杨醛 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 2-(N-salicylideneaminomethyl)benzimidazole
  参考文献：
  名称：

  三齿吡啶基和苯并咪唑基配体的铁（III）配合物的合成，结构，光谱和氧化还原化学

  摘要：

  水杨醛和芳香胺衍生的席夫碱的一系列高自旋八面体1：2铁（III）配合物以及双（吡啶-2-基）-氮杂和双（苯并咪唑-已经分离出2-基）-氮杂和-硫醚配体。已经确定了三氯[双（吡啶-2-基甲基）胺]铁（III）的晶体结构。它在不对称晶胞中包含两个晶体学独立的分子。在每个分子中，铁（III）具有菱形扭曲的八面体配位，由面部配体的所有三个氮原子和三个氯离子组成。立体化学和/或供体原子变化对UV / VIS和EPR光谱以及Fe III –Fe II的影响讨论了氧化还原电势以及铁（III）中心的路易斯酸度。[FeL 1 2 ] Cl [HL 1 = N-（吡啶-2-基甲基）水杨基亚胺]的酚盐对铁（III）电荷转移带能更高，其Fe III -Fe II氧化还原电位比对应的1：1复合物的那些。

  DOI：

  10.1039/dt9960002519

文献信息

• Mitochondria‐Targeting Oxidovanadium(IV) Complex as a Near‐IR Light Photocytotoxic Agent
  作者：Puja Prasad、Imran Khan、Paturu Kondaiah、Akhil R. Chakravarty

  DOI：10.1002/chem.201303487

  日期：2013.12.16

  443 nm. The complexes are redox‐active exhibiting the V(IV)/V(III) redox couple near −0.85 V versus SCE in DMF 0.1 M tetrabutylammonium perchlorate (TBAP). Complex 2, having a dipeptide moiety, showed specific binding towards poly(dAdT)2 sequence. The dppz‐Gly‐Gly‐OMe complex showed significant DNA photocleavage activity in red light of 705 nm through a hydroxyl radical (.OH) pathway. Complex 2 showed

  Oxidovanadium（IV）配合物[VO（L 1）（phen）的] ⋅氯（1）和[VO（L 2）（L 3）] ⋅氯（2），其中HL 1是2 - [（苯并咪唑（2-基）甲基亚氨基]-甲基}苯酚（sal-ambmz），HL 2是2-[（1-[（（蒽基-9-基）]]] [苯并咪唑-2- [基}甲基亚氨基]-甲基]苯酚（ （sal-an-ambmz），phen是1,10-菲咯啉，L 3是与Gly-Gly-OMe二肽部分共轭的二吡啶[3,2-a：2'，3'-c]吩嗪（dppz），制备，表征并研究了它们的DNA结合，光诱导的DNA裂解和光细胞毒性特性。使用复合物2进行荧光显微镜研究在HeLa和HaCaT细胞中。复杂1，在结构上，其特征在于X-射线晶体学，在VO氧钒基2 Ñ 4与VO芯2+键合到N，N-供啉和N，N，O部分-供体的席夫碱。具有蒽基荧光团的配合物2在397、419和443nm处显
• Synthesis, Characterization, Reactivity, and Catalytic Potential of Model Vanadium(IV, V) Complexes with Benzimidazole-Derived ONN Donor Ligands
  作者：Mannar R. Maurya、Amit Kumar、Martin Ebel、Dieter Rehder

  DOI：10.1021/ic0604922

  日期：2006.7.1

  and 10 lead to (reversible) protonation of the bemzimidazole, while 8 was converted to an oxo-hydroxo species. Complexes 2, 4, and 8 catalyze the oxidation of methyl phenyl sulfide to methyl phenyl sulfoxide and methyl phenyl sulfone, a reaction mimicking the sulfideperoxidase activity of vanadate-dependent haloperoxidases. These complexes are also catalytically active in the oxidation of styrene to styrene

  [VO（acac）（2）]与ONN供体Schiff碱Hsal-ambmz（I）（Hsal-ambmz =通过水杨醛和2-氨基甲基苯并咪唑缩合获得的Schiff碱）之间的反应导致形成络合物[V （IV）O（acac）（sal-ambmz）]（1），[V（V）O（2）（acac-ambmz）]（2）（Hacac-ambmz =源自乙酰丙酮和2-氨基甲基苯并咪唑的席夫碱） ，以及已知的络合物[V（IV）O（sal-phen）]（3）（H（2）sal-phen =来自水杨醛和邻苯二胺的席夫碱）。同样，[V（IV）O（acac）（sal-aebmz）]（7）已从与Hsal-aebmz（II）（水杨醛和2-氨基乙基苯并咪唑衍生的Hsal-aebmz）的反应中分离出来。空中氧化1和7的甲醇溶液/悬浮液得到二氧钒（V）络合物[V（V）O（2）（sal-ambmz）]（4）和[V（V）O（2）（sal- a
• DNA binding, DNA cleavage, cellular uptake, cytotoxicity, and apoptosis-inducing ability of a binuclear Schiff base copper(<scp>ii</scp>) complex
  作者：Dandan Zhao、Yixuan Wu、Wenxin Huang、Silin Gong、Zhanfen Chen

  DOI：10.1039/d2nj03077b

  日期：——

  binuclear Schiff base copper(II) complex [Cu2(L-H)2]Cl2 (1, L = N-(2-hydroxylbenzylidene)-benzo[d]imidazol-2-amine) was synthesized and characterized by elemental analysis, ESI-MS, HRMS, IR, and molar conductivity. Magnetization measurements revealed that 1 showed the usual, moderate-to-strong intramolecular antiferromagnetically coupling exchange interaction between two copper(II) centers. The electrochemical

  合成了一种双核席夫碱铜( II )配合物[Cu 2 ( L -H) 2 ]Cl 2 ( 1 , L = N -(2-hydroxylbenzylidene)-benzo[ d ]imidazol-2-amine)并通过元素表征分析、ESI-MS、HRMS、IR 和摩尔电导率。磁化测量表明，1显示了两个铜 ( II ) 中心之间通常的、中等到强的分子内反铁磁耦合交换相互作用。DMF 中的电化学行为表明，1遵循准不可逆性质，连续两次单电子还原如下：Cu II Cu II ⇔ Cu II Cu I ⇔ Cu I Cu I。复合物1可以通过凹槽结合模式和静电相互作用与 DNA 结合，并诱导 DNA 的构象变化。此外，1可以通过氧化机制有效地将超螺旋质粒 DNA 切割成切口和线性形式。细胞实验表明1能有效进入癌细胞，甚至细胞核，诱导细胞凋亡，对HeLa和A549细胞系表现出与顺铂相当的细胞毒性；它还对
• Synthesis, interaction with DNA and antiproliferative activities of two novel Cu(II) complexes with Schiff base of benzimidazole
  作者：Wen-Ji Song、Jian-Ping Cheng、Dong-Hua Jiang、Li Guo、Meng-Fei Cai、Hu-Bin Yang、Qiu-Yue Lin

  DOI：10.1016/j.saa.2013.09.142

  日期：2014.3

  Two novel copper(II) complexes with Schiff base of benzimidazole [Cu(L)Cl](2)center dot CH3OH have been synthesized. HL1 (N-(benzimidazol-2-ymethyl)-5-chlorosalicylideneimine, C15H11ClN3O) and HL2 (N-(benzimidazol-2-ymethyl)-salicylideneimine, C15H12N3O) are ligands of complex (I) and complex (2), respectively. The complexes were characterized by elemental analysis, IR, UV-Vis, TGA and X-ray diffraction. Within the complexes, Cu(II) ions were four coordinated by two nitrogen atom of azomethine and imine, one phenolic oxygen atom from HL and one chloride atom. A distorted quadrilateral structure was formed. Complex (1) crystallized in the triclinic crystal system. Results showed that pi-pi stacking effect occurred due to the existence of aromatic ring from Schiff base and hydrogen bonding between methanol and adjacent atoms. The DNA binding properties of the complexes were investigated by electronic absorption spectra, fluorescence spectra and viscosity measurements. Results indicated that complexes bound to DNA via partial intercalation mode. The DNA binding constants K-b/(L mol(-1)) were 1.81 x 10(4) (1), 1.37 x 10(4) (2), 6.27 x 10(3) (HL1) and 3.14 x 10(3) (HL2) at 298 K. The title complexes could quench the emission intensities of EB-DNA system significantly. The results of agarose gel electrophoresis indicated complex (1) could cleave supercoiled DNA through the oxidative mechanism. The inhibition ratios revealed that complex (1) and HL1 had strong antiproliferative activities against human breast cancer cells (MCF-7) lines and human colorectal cancer cells (COLO205) lines in vitro. The antiproliferative activities of complex (1) against MCF-7 lines (IC50 = 16.9 +/- 1.5 mu mol L-1) and against COLO205 lines (IC50 = 16.5 +/- 3.4 mu mol L-1) is much stronger than that of HL1, which had the potential to develop anticancer drug. (C) 2013 Elsevier B.V. All rights reserved.
• Oxidation of phenol, styrene and methyl phenyl sulfide with H2O2 catalysed by dioxovanadium(V) and copper(II) complexes of 2-aminomethylbenzimidazole-based ligand encapsulated in zeolite-Y
  作者：Mannar R. Maurya、Anil K. Chandrakar、Shri Chand

  DOI：10.1016/j.molcata.2006.08.084

  日期：2007.2

  Interaction of oxovanadium(IV) exchanged zeolite-Y with the Schiff base derived from salicylaldehyde and 2-aminomethylbenzimidazole (Hsal-ambmz) in refluxing methanol followed by aerial oxidation leads to the formation of encapsulated dioxovanadium(V) complex, [VO2(sal-ambmz)]+Y(1). Similar reaction with copper(II) exchanged zeolite-Y followed by its treatment with aqueous NaCl gave encapsulated copper(II) complex, [Cu(sal-ambmz)Cl]-Y(2). These encapsulated complexes have been characterized by spectroscopic studies, thermal analysis and scanning electron micrographs (SEMs) as well as X-ray diffraction patterns. 3D model structure generated for neat complex [VO2(sal-ambmz)] suggests that zeolite-Y can accommodate these complexes in its nano-cavity without any strain. The encapsulated materials are active catalysts for the oxidation of phenol, styrene and methyl phenyl sulfide using H2O2 as an oxidant. Under the optimised reaction conditions about 42% conversion of phenol was obtained with these catalysts where the selectivity of catechol varied in the order: 2 (73.9%) > 1 (65.2%). With the conversion of 97.0% with 1 or 56.7% with 2, the oxidation of styrene gave styrene oxide, benzaldehyde, benzoic acid, 1-phenyl ethane-1,2-diol and phenylacetaldehyde as major products. A maximum of 96.1% (with 1) conversion of methyl phenyl sulfide was observed in which the selectivity of major product methyl phenyl sulfoxide was found to be ca. 98%. (c) 2006 Elsevier B.V. All rights reserved.