A new ionic compound ｛[2-(3′-pyridyl)benzimidazoleH2]2+·[SbCl4]-·Cl-｝4 was synthesized by the hy- drothermal reaction of o-diaminobenzene, nicotinic acid with SbCl3 in 1∶1 HCl solution. The structure was...A new ionic compound ｛[2-(3′-pyridyl)benzimidazoleH2]2+·[SbCl4]-·Cl-｝4 was synthesized by the hy- drothermal reaction of o-diaminobenzene, nicotinic acid with SbCl3 in 1∶1 HCl solution. The structure was charac- terized by chemical analysis, elemental analysis and IR patterns. The single crystal structure was determined by X-ray single crystal diffraction. It crystallizes in monoclinic system, space group P21/n with a=2.107 9(4) nm, b= 1.482 0(3) nm, c=2.113 4(4) nm, β=93.44(3)°, Z=4, V=6.590(2) nm3, Dc=2.001 g·cm-3, μ=2.480 mm-1, F(000)= 3840, R1=0.0468, wR2=0.1163. The single crystal structure indicates that the four chlorines coordinated to the antimony atom forms a distorted triangle bipyramid configuration together with the lone electron pair on the Sb atom. The [SbCl4]- to 2-(3′-pyridyl)benzimidazole cation and Cl- by weak interaction forms the ionic crystal. It has been proved that the title compound has antibacterial activity. CCDC: 283824.展开更多
A new supramolecular compound, { [2-（2-pyridyl）benzimidazoleH2]2＋.[SBC15]2-}2, was synthesized by the hydrothermal reaction of o-diaminobenzene, 2-pyridinecarboxylie acid and SbCl3 in 1：1 HC1 solution, and charact...A new supramolecular compound, { [2-（2-pyridyl）benzimidazoleH2]2＋.[SBC15]2-}2, was synthesized by the hydrothermal reaction of o-diaminobenzene, 2-pyridinecarboxylie acid and SbCl3 in 1：1 HC1 solution, and characterized by chemical analysis, elemental analysis, IR spectra, thermogravimetfic analysis and fluorescence spectra. The crystal structure was deter- mined by X-ray single-crystal diffraction. The crystal belongs to the monoclinic system, space group P211c, with a = 16.0397（13）, b = 14.3189（12）, c = 15.6370（13） A, β = 105.8980（10）°, V = 3454.0（5） A3, Z = 4, C24H22Cl10N6Sb2, Mr = 992.48, Dc = 1.909 g/cm3,/z = 2.366 mm-1, S = 1.010, F（000） = 1920, R = 0.0254 and wR = 0.0555. The coordination anion, [SbCl5]2- which is a distorted tetragonal pyramid, is composed by coordinating action with Sb3＋ ion and five adjacent chloride ions. Every four coordination anions of [SbCl5]2- form a biquaternion ring structure through the secondary bonding of Sb...Cl. Moreover, the compound adopts a three-dimensional network supramolecular structure because of the hydrogen bonds and π-π stacking between the rings and the 2-（2-pyridyl）benzimidazole divalent cations. The title compound also shows good fluorescent behaviors.展开更多
Glyoxylic acid （5 mol%） performs as a novel highly water-soluble catalyst for the synthesis of 2-aryl-l-arylmethyl-lH- benzimidazoles from a wide range of substituted o-phenylenediamines and various substituted alde...Glyoxylic acid （5 mol%） performs as a novel highly water-soluble catalyst for the synthesis of 2-aryl-l-arylmethyl-lH- benzimidazoles from a wide range of substituted o-phenylenediamines and various substituted aldehydes in good to excellent isolated yields （85-95%） using water as solvent at ambient temperature. The remarkable advantages offered by this method are easily and inexpensive available catalyst, simple procedure, mild conditions, much faster （20--40 rain） reactions and excellent yields of products.展开更多
Differently substituted benzimidazoles have been synthesized in very good yields in solvent-free conditions from o-phenylenediamine and aldehydes in the presence of BF3·OEt2 as a catalyst. The method is applicabl...Differently substituted benzimidazoles have been synthesized in very good yields in solvent-free conditions from o-phenylenediamine and aldehydes in the presence of BF3·OEt2 as a catalyst. The method is applicable to aromatic, unsaturated and aliphatic aldehydes and to substituted o-phenylenediamines without significant differences.展开更多
A novel Ru（Ⅱ） complex [（bpy）2Ru（PBC）]（PF6）2 （PBC = N-[4-（9-carbazole）butyl]-2-（2-pyridyl）benzimidazole） has been synthesized and verified by 1↑H NMR, elemental analysis and X-ray crystallography. The c...A novel Ru（Ⅱ） complex [（bpy）2Ru（PBC）]（PF6）2 （PBC = N-[4-（9-carbazole）butyl]-2-（2-pyridyl）benzimidazole） has been synthesized and verified by 1↑H NMR, elemental analysis and X-ray crystallography. The crystal （C48H40F12N8P2Ru, Mr = 1119.89） belongs to the triclinic system, space group P1, with a = 13.128（4）, b = 13.814（4）, c = 14.184（4） A, α = 84.112（6）, β = 88.473（6）, γ = 78.196（6）°, Z = 2, V = 2504.6（13）A^3, Dc = 1.485 g/cm^3, F（000） = 1132, R = 0.0750 and wR = 0.1896. The Ru atom adopts a distorted-octahedral coordination geometry with the bond distances and bond angles falling in normal ranges. The complex shows an intense metal-to-ligand charge transfer （1MLCT） （dπ（Ru） →π＊（L）） transition （ε ~1.2×10^4 dm^3mol^-1cm^-1） at 457 nm in the UV-Vis absorption spectrum and a strong red phosphorescence at 632 nm in the CH3CN solution at ambient temperature. An efficient intramolecular energy transfer process from the carbazole unit to the [（bpy）2Ru（PB）]^2＋ emissive center exists by selective optical-simulation. Its electrochemical behavior shows multiplicate redox processes based on the metal center, the grafting carbazole moiety and the 2-（2-pyridyl）benzimidazole unit.展开更多
A novel supramolecular compound,{[2-（2-pyridyl）benzimidazoleH2]2·[BiCl6]·Cl},was synthesized by the hydrothermal reaction of o-phenylenediamine and α-pyridinecarboxylic acid with BiCl3 in 6.0 mol·L-1...A novel supramolecular compound,{[2-（2-pyridyl）benzimidazoleH2]2·[BiCl6]·Cl},was synthesized by the hydrothermal reaction of o-phenylenediamine and α-pyridinecarboxylic acid with BiCl3 in 6.0 mol·L-1 HCl solution,and characterized by elemental analysis,IR,X-ray single-crystal diffraction and photoluminescence spectroscopy.The crystal （C24H22N6Cl7Bi,Mr= 851.61） belongs to the triclinic system,space group P1 with a =7.2887（18）,b =9.548（2）,c= 12.469（3）,α=85.306（4）,β=82.814（4）,γ=71.349（4）°,Z=1,V=814.9（3）3,Dc=1.735 g/cm3,μ（MoKα）=6.007 mm-1,F（000）=410,R=0.0307 and wR=0.0787.The bismuth ion and six chlorine ions construct a distorted octahedral configuration.The three-dimensional supramolecular network is built from electrostatic attractions,hydrogen bonds and π-π interaction between the BiCl6 anion,Cl anion and [2-（2-pyridyl）benzimidazoleH2] cation.The photoluminescence spectroscopy study shows that the title compound has a blue fluorescent emission at 450 nm in the solid state.展开更多
The reactions of SbCl3 and HgCl2 with 2-（3-pyridyl）benzimidazole （PyBIm） in solution acidified with HCl have been investigated. The PyBIm ligands are protonated into 2-（3-pyridinio）benzimidazolium （H2PyBIm） ca...The reactions of SbCl3 and HgCl2 with 2-（3-pyridyl）benzimidazole （PyBIm） in solution acidified with HCl have been investigated. The PyBIm ligands are protonated into 2-（3-pyridinio）benzimidazolium （H2PyBIm） cations and the corresponding metal ions are bonded with chloride atoms into coordination anions, forming two new coordination compounds, namely, （H2PyBIm）（SbCl5） 1 and （H2PyBIm）2（Hg2Cl8） 2. Both compounds were characterized by X-ray crystallography. Crystal data for 1： triclinic, space group P1^- with a = 5.7030（7）, b = 9.0625（11）, c = 16.5929（18） A, α = 91.808（7）°, β = 93.234（6）, γ = 99.216（7）°, C12H11N3SbCl5, Mr = 496.24, V = 844.44（17） A^3, Z = 2, Dc = 1.952 g/cm^3, μ（MoKα） = 2.419 mm^-1, F（000） = 480, the final R = 0.0496 and wR = 0.1382 for 3433 observed reflections （I 〉 2σ（I））. Crystal data for 2： monoclinic, space group P21/c with a = 7.8061（5）, b = 15.8127（9）, c = 12.2435（9） , β = 91.955（4）o, C24H22N6Hg2Cl8, Mr = 1079.26, V = 1510.40（17） 3, Z = 2, Dc = 2.373 g/cm3, μ（MoKα） = 10.889 mm-1, F（000） = 1008, the final R = 0.0293 and wR = 0.0562 for 2854 observed reflections （I 〉 2σ（I））. X-ray diffraction analysis reveals that the antimony（III） is five-coordinated, exhibiting a slightly distorted square-pyramidal coordination geometry; while in 2, a dimeric [Hg2Cl8]^4-anion consists of two trigonal bipyramids sharing two common edges. The organic cations and coordination anions are connected into a one-dimensional belt and a two-dimensional sheet through N-H···Cl hydrogen bonding interactions in compounds 1 and 2, respectively; both are further aggregated into 3D frameworks by strong π-π contacts.展开更多
A double-T-shaped ligand （H4BPTC） and bis（2-benzimidazole）alkanes as the spacers have been firstly used to direct the assembly of a 2D coordination polymer with wavy parquet network topology, [Zn（BPTC）0.5（H2C2...A double-T-shaped ligand （H4BPTC） and bis（2-benzimidazole）alkanes as the spacers have been firstly used to direct the assembly of a 2D coordination polymer with wavy parquet network topology, [Zn（BPTC）0.5（H2C2EIm）（H2O）]n （1, C24H18ZnN4O5, Mr = 507.79, H4BPTC = biphenyl-3,3＇,4,4＇-tetracarboxylic acid, H2C2EIm = 2,2＇-（1,2-ethanediyl）-bis（1H-benzi- midazole）, which was determined by single-crystal X-ray diffraction analysis. The crystal belongs to the monoclinic system, space group P21/n with a = 1.1844（5）, b = 1.4019（5）, c = 1.4026（5） nm, β = 108.359（5）°, V = 2.2104（15） nm3, Z = 4, Dc = 1.526 g/cm3, μ（MoKα） = 1.156 mm-1, F（000） = 1040, S = 1.038, the final R = 0.0427 and wR = 0.0793 for 3834 reflections with I 2σ（I）. The compound units are linked through BPTC ligands into a wavilness parquet 2D layer and further connected into a 3D framework via π-π packing interactions between the adjacent H2C2EIm ligands and weak N-H…O hydrogen bonding between uncoordinated carboxylate and the nitrogen atoms of H2C2EIm as well as the free water molecules.展开更多
A convenient method to synthesize substituted 2 (2' hydroxyphenyl) benzimidazoles is reported. Six title compounds have been synthesized by the reaction of salicylic acid and 4 substituted o phenylene...A convenient method to synthesize substituted 2 (2' hydroxyphenyl) benzimidazoles is reported. Six title compounds have been synthesized by the reaction of salicylic acid and 4 substituted o phenylenediamine in the presence pyridine POCl 3 . Three compounds were tested as plant virucide against tobacco mosaic virus and they exhibited some activities.展开更多
<span style="font-family:Verdana;">A series of novel substituted benzimidazole </span><b><span style="font-family:Verdana;">(7a</span></b><b><span style...<span style="font-family:Verdana;">A series of novel substituted benzimidazole </span><b><span style="font-family:Verdana;">(7a</span></b><b><span style="font-family:;" "=""> </span></b><b><span style="font-family:Verdana;">-</span></b><b><span style="font-family:;" "=""> </span></b><b><span style="font-family:Verdana;">n)</span></b><span style="font-family:Verdana;"> derivatives w</span><span style="font-family:Verdana;">ere</span><span style="font-family:;" "=""><span style="font-family:Verdana;"> synthesized and characterized by </span><sup><span style="font-family:Verdana;">1</span></sup><span style="font-family:Verdana;">H, </span><sup><span style="font-family:Verdana;">13</span></sup><span style="font-family:Verdana;">C Nuclear Magnetic Resonance (NMR) spectra and High Resolution Mass Spectrometry (HRMS). The substitution w</span></span><span style="font-family:Verdana;">as</span><span style="font-family:;" "=""><span style="font-family:Verdana;"> done in position -1 and -2 by appropriate groups. These compounds are obtained by N-alkylation reaction with thiomethyl-1</span><i><span style="font-family:Verdana;">H</span></i><span style="font-family:Verdana;">-benzimidazole intermediates </span><b><span style="font-family:Verdana;">(5a</span></b></span><b><span style="font-family:;" "=""> </span></b><b><span style="font-family:Verdana;">-</span></b><b><span style="font-family:;" "=""> </span></b><b><span style="font-family:Verdana;">g)</span></b><span style="font-family:;" "=""><span style="font-family:Verdana;">. Design of intermediates </span><b><span style="font-family:Verdana;">(5a</span></b></span><b><span style="font-family:;" "=""> </span></b><b><span style="font-family:Verdana;">-</span></b><b><span style="font-family:;" "=""> </span></b><b><span style="font-family:Verdana;">g)</span></b><span style="font-family:;" "=""><span style="font-family:Verdana;"> was made by condensation reaction between 2-methylbenzimidazole thiourunium salt </span><b><span style="font-family:Verdana;">(3)</span></b><span style="font-family:Verdana;"> and functionalized halides </span><b><span style="font-family:Verdana;">(4)</span></b><span style="font-family:Verdana;"> in the presence of sodium hydroxide (NaOH). Among the </span><span style="font-family:Verdana;">twenty-one compounds synthesized, ten were evaluated for their antimi</span><span style="font-family:Verdana;">crobial activity on three bacterial strains namely: </span><i><span style="font-family:Verdana;">Escherichia</span></i> <i><span style="font-family:Verdana;">coli</span></i><span style="font-family:Verdana;"> ATCC 25922, </span><i><span style="font-family:Verdana;">Staphylococcus</span></i> <i><span style="font-family:Verdana;">aureus</span></i><span style="font-family:Verdana;"> ATCC 25923 and </span><i><span style="font-family:Verdana;">Pseudomonas</span></i> <i><span style="font-family:Verdana;">aeruginosa</span></i><span style="font-family:Verdana;"> ATCC 27853. Only </span><i><span style="font-family:Verdana;">E.</span></i> <i><span style="font-family:Verdana;">coli</span></i><span style="font-family:Verdana;"> ATTC 25922 was susceptible to the synthesized derivatives </span><b><span style="font-family:Verdana;">5g</span></b><span style="font-family:Verdana;">, </span><b><span style="font-family:Verdana;">7f</span></b><span style="font-family:Verdana;"> and </span><b><span style="font-family:Verdana;">7h</span></b><span style="font-family:Verdana;"> with a significant antibacterial activity (CMI </span></span><span style="font-family:Verdana;">is </span><span style="font-family:Verdana;">between 250 and 500 μg/mL)</span><span style="font-family:Verdana;">.</span>展开更多
On the base of benzimidazole and benzofuran containing heterocyclic system, several derivatives with expected biological activity were synthesized. 2,3-diaminodibenzofuran was the primary substance. Adding various cyc...On the base of benzimidazole and benzofuran containing heterocyclic system, several derivatives with expected biological activity were synthesized. 2,3-diaminodibenzofuran was the primary substance. Adding various cyclic agents, 2-phenil was got, 2-（o-chlorophenil）, 2-（o-oxyphenil）, 2-chlorometyl- and 2-hydroximethyl-3H-benzo[b[furo（3,2-f] benzimidazoles. The aforementioned substances were characterized by IR and NMR spectroscopy.展开更多
A fast, high efficiency and environmentally friendly procedure for the synthesis of 2-aryl benzim-idazole derivatives has been reported. Reaction between 1,2-phenylenediamine derivatives and arylidene malononitrile un...A fast, high efficiency and environmentally friendly procedure for the synthesis of 2-aryl benzim-idazole derivatives has been reported. Reaction between 1,2-phenylenediamine derivatives and arylidene malononitrile under aqueous media and also solvent-free conditions generates 2-aryl benzimidazole derivatives with a high yield.展开更多
A new method of synthesis of 2-(1,2-diferrocenylvinyl)benz- and azabenzimidazoles (3a-f), (4a-f) and 1’H,3’H(Me)-spiro-[(aza)benzimidazoline-2’,3-(1,2-diferrocenylcyclopropenes)] (5a-f) via reactions of diferroceny...A new method of synthesis of 2-(1,2-diferrocenylvinyl)benz- and azabenzimidazoles (3a-f), (4a-f) and 1’H,3’H(Me)-spiro-[(aza)benzimidazoline-2’,3-(1,2-diferrocenylcyclopropenes)] (5a-f) via reactions of diferrocenyl(methylsulfanyl)cyclopropenylium iodide (1) with aromatic o-diamines (2a-f) in the presence of Et3N (80°C - 82°C) is described. The structures of the resultant compounds are established using IR, 1H and 13C NMR spectroscopy, mass spectrometry and elemental analysis. The structure of one compound, cis-2-(1,2-diferrocenylvinyl)-1-methylbenzimidazole (3b), is confirmed by X-ray diffraction analysis. The electrochemical properties of compounds 3a, 3b, 3d and 5f are investigated using cyclic square wave voltammetry. Two electrochemical processes (I-II), attributed to oxidation of the ferrocene moieties, and the values of E0’(I), E0’(II), DE0’(II-I) and comporportionation constant Kcom are reported. The bioactivities of seven compounds 3a, 3c-f, 5d, 5f are evaluated. Compound 5f is the most active compound with a modest cytotoxic activity against six human cancer cell lines: U-251 (glioma), PC-3 (prostate cancer), K-562 (leukemia), HCT-15 (colon cancer), MCF-7 (breast cancer) and SKLU-1 (lung cancer).展开更多
A new cadmium（Ⅱ） nitrite complex Cd2（H2C3PIm）2（BDC）（NO2）2（1,H2C3PIm = 2,2＇-（1,3-propanediyl）bis（1H-benzimidazole）,H2BDC = 1,4-benzenedicarboxylic acid） has been synthesized by solvothermal reaction in ...A new cadmium（Ⅱ） nitrite complex Cd2（H2C3PIm）2（BDC）（NO2）2（1,H2C3PIm = 2,2＇-（1,3-propanediyl）bis（1H-benzimidazole）,H2BDC = 1,4-benzenedicarboxylic acid） has been synthesized by solvothermal reaction in formamide,and its structure（C42H36Cd2N10O8,Mr = 1033.61） was determined by single-crystal X-ray diffraction analysis.The crystal belongs to the monoclinic system,space group P21/n with a = 0.9859（5）,b = 0.8936（5）,c = 2.3188（5） nm,β = 97.576（5）°,V = 2.025（16） nm3,Z = 2,Dc = 1.695 g/cm3,μ（MoKα） = 1.118 mm-1,F（000） = 1036,S = 1.017,the final R = 0.0304 and wR = 0.0752 for 3761 reflections with I 〉 2σ（I）.The centrosymmetric complex 1 contains a dimer in which two distorted octahedral Cd（II） centers are bridged by BDC ligand and chelated by H2C3PIm.The units of the complex are linked via weak N-H···O hydrogen bonds between the nitrito and the BDC ligands,leading to the formation of a 1D zigzag chain along the b axis.The π-π packing interactions contribute to the formation of a three-dimensional supramolecular architecture.The complex exhibits strong photoluminescence at room temperature.展开更多
In order to discover the novel anti-tumor agents, a series of 2-[（pyridin-2-yl）methylthio]-1 H-benzimidazole derivatives were designed and synthesized, and the structures were characterized by IR, MS, and proton NMR...In order to discover the novel anti-tumor agents, a series of 2-[（pyridin-2-yl）methylthio]-1 H-benzimidazole derivatives were designed and synthesized, and the structures were characterized by IR, MS, and proton NMR. 2-[（3,4-Dimethoxypyridin-2-yl）methylthio]-1 Hbenzimidazole was investigated with X-ray crystallography, and the molecule is in orthorhombic system, space group P212121, with a = 9.1828（16）, b = 11.625（2）, c = 13.463（2） ？, Z = 4, R = 0.0231 and wR = 0.0596. The antitumor activities of target compounds were evaluated against human liver cancer cell line HepG2, and human liver normal cell line HL7702 using MTT assay. The target compounds have demonstrated weak or moderate anti-tumor activity against HepG2, while all the target compounds exhibit no cytotoxic effects on HL7702.展开更多
Dimethylaminophenyl)-5-fluoro-6-(morpholin-4-yl)-1H-benzimidazole(1) has been synthesized and characterized by H-NMR, MS and elemental analysis. UV-Vis spectra of the 1 aqueous solutions at different pH values reveal ...Dimethylaminophenyl)-5-fluoro-6-(morpholin-4-yl)-1H-benzimidazole(1) has been synthesized and characterized by H-NMR, MS and elemental analysis. UV-Vis spectra of the 1 aqueous solutions at different pH values reveal that compound 1 can combine three protons. Its three protonation constants are determined by spectrophotometry and calculated by non-linear least squares. The results of steady-state fluorescence measurements indicate that a special interaction occurs between compound 1 and calf thymus DNA, of which the binding constant, Kb, is (2.30 ± 0.10)×l04 L/mol. Compound 1 in the concentration range of 10-8 to 1.2×10-6 mol/L could be used for quantitative determination of DNA.展开更多
The Iead compound of substituted 2-(4-hydroxyphenyl)benzimidazol were modified by phos-phorylation sulfonation and carboxymethylation. The henzimldazoloamidophosphate (6) (7) have better activi-ty against tobacco mosa...The Iead compound of substituted 2-(4-hydroxyphenyl)benzimidazol were modified by phos-phorylation sulfonation and carboxymethylation. The henzimldazoloamidophosphate (6) (7) have better activi-ty against tobacco mosaic virus (TMV). The benzimldazolophenoxyacetic acid, phenoxysuIfonic acid c0ntaining tri flu0r0methyl, and nitro gr0up have 77% ~85% efflclency f0r wheat rust disease.展开更多
Three sulfhydryl-reactive fluorescent probes, which contain 2-（1H-benzoimidazol-2-yl）-phenol and maleimide group, were synthesized and their structures were characterized by IR and ^1H NMR. Their photo-physical prop...Three sulfhydryl-reactive fluorescent probes, which contain 2-（1H-benzoimidazol-2-yl）-phenol and maleimide group, were synthesized and their structures were characterized by IR and ^1H NMR. Their photo-physical properties and the specificity to sulfhydryl group in the 2-mercapto-ethanol as well as the L-cysteine adducts were indicated by fluorescence intensity. Preliminary tests revealed that the probes could react selectively with the cysteine molecules, suggesting that these probes might be generally useful in biomedical researches.展开更多
文摘A new ionic compound ｛[2-(3′-pyridyl)benzimidazoleH2]2+·[SbCl4]-·Cl-｝4 was synthesized by the hy- drothermal reaction of o-diaminobenzene, nicotinic acid with SbCl3 in 1∶1 HCl solution. The structure was charac- terized by chemical analysis, elemental analysis and IR patterns. The single crystal structure was determined by X-ray single crystal diffraction. It crystallizes in monoclinic system, space group P21/n with a=2.107 9(4) nm, b= 1.482 0(3) nm, c=2.113 4(4) nm, β=93.44(3)°, Z=4, V=6.590(2) nm3, Dc=2.001 g·cm-3, μ=2.480 mm-1, F(000)= 3840, R1=0.0468, wR2=0.1163. The single crystal structure indicates that the four chlorines coordinated to the antimony atom forms a distorted triangle bipyramid configuration together with the lone electron pair on the Sb atom. The [SbCl4]- to 2-(3′-pyridyl)benzimidazole cation and Cl- by weak interaction forms the ionic crystal. It has been proved that the title compound has antibacterial activity. CCDC: 283824.
基金Supported by the Natural Science Foundation of Henan Province (No. 0611023700)Natural Science Foundation of Education Department of Henan Province (No. 2006150019)
文摘A new supramolecular compound, { [2-（2-pyridyl）benzimidazoleH2]2＋.[SBC15]2-}2, was synthesized by the hydrothermal reaction of o-diaminobenzene, 2-pyridinecarboxylie acid and SbCl3 in 1：1 HC1 solution, and characterized by chemical analysis, elemental analysis, IR spectra, thermogravimetfic analysis and fluorescence spectra. The crystal structure was deter- mined by X-ray single-crystal diffraction. The crystal belongs to the monoclinic system, space group P211c, with a = 16.0397（13）, b = 14.3189（12）, c = 15.6370（13） A, β = 105.8980（10）°, V = 3454.0（5） A3, Z = 4, C24H22Cl10N6Sb2, Mr = 992.48, Dc = 1.909 g/cm3,/z = 2.366 mm-1, S = 1.010, F（000） = 1920, R = 0.0254 and wR = 0.0555. The coordination anion, [SbCl5]2- which is a distorted tetragonal pyramid, is composed by coordinating action with Sb3＋ ion and five adjacent chloride ions. Every four coordination anions of [SbCl5]2- form a biquaternion ring structure through the secondary bonding of Sb...Cl. Moreover, the compound adopts a three-dimensional network supramolecular structure because of the hydrogen bonds and π-π stacking between the rings and the 2-（2-pyridyl）benzimidazole divalent cations. The title compound also shows good fluorescent behaviors.
基金Head,Department of Chemistry,Vinayakrao Patil Mahavidyala Vaijapur 423701(M.S.),India,for partial support of this work.
文摘Glyoxylic acid （5 mol%） performs as a novel highly water-soluble catalyst for the synthesis of 2-aryl-l-arylmethyl-lH- benzimidazoles from a wide range of substituted o-phenylenediamines and various substituted aldehydes in good to excellent isolated yields （85-95%） using water as solvent at ambient temperature. The remarkable advantages offered by this method are easily and inexpensive available catalyst, simple procedure, mild conditions, much faster （20--40 rain） reactions and excellent yields of products.
文摘Differently substituted benzimidazoles have been synthesized in very good yields in solvent-free conditions from o-phenylenediamine and aldehydes in the presence of BF3·OEt2 as a catalyst. The method is applicable to aromatic, unsaturated and aliphatic aldehydes and to substituted o-phenylenediamines without significant differences.
基金Supported by the Natural Science Foundation of Henan Province (No. 102100410221)the Natural Science Foundation of Nanyang Normal University (No. ZX2010012)the Young Core Instructor from the Education Commission of Henan Province
文摘A novel Ru（Ⅱ） complex [（bpy）2Ru（PBC）]（PF6）2 （PBC = N-[4-（9-carbazole）butyl]-2-（2-pyridyl）benzimidazole） has been synthesized and verified by 1↑H NMR, elemental analysis and X-ray crystallography. The crystal （C48H40F12N8P2Ru, Mr = 1119.89） belongs to the triclinic system, space group P1, with a = 13.128（4）, b = 13.814（4）, c = 14.184（4） A, α = 84.112（6）, β = 88.473（6）, γ = 78.196（6）°, Z = 2, V = 2504.6（13）A^3, Dc = 1.485 g/cm^3, F（000） = 1132, R = 0.0750 and wR = 0.1896. The Ru atom adopts a distorted-octahedral coordination geometry with the bond distances and bond angles falling in normal ranges. The complex shows an intense metal-to-ligand charge transfer （1MLCT） （dπ（Ru） →π＊（L）） transition （ε ~1.2×10^4 dm^3mol^-1cm^-1） at 457 nm in the UV-Vis absorption spectrum and a strong red phosphorescence at 632 nm in the CH3CN solution at ambient temperature. An efficient intramolecular energy transfer process from the carbazole unit to the [（bpy）2Ru（PB）]^2＋ emissive center exists by selective optical-simulation. Its electrochemical behavior shows multiplicate redox processes based on the metal center, the grafting carbazole moiety and the 2-（2-pyridyl）benzimidazole unit.
基金Supported by the Natural Science Foundation of Henan Province (No. 0611023700)
文摘A novel supramolecular compound,{[2-（2-pyridyl）benzimidazoleH2]2·[BiCl6]·Cl},was synthesized by the hydrothermal reaction of o-phenylenediamine and α-pyridinecarboxylic acid with BiCl3 in 6.0 mol·L-1 HCl solution,and characterized by elemental analysis,IR,X-ray single-crystal diffraction and photoluminescence spectroscopy.The crystal （C24H22N6Cl7Bi,Mr= 851.61） belongs to the triclinic system,space group P1 with a =7.2887（18）,b =9.548（2）,c= 12.469（3）,α=85.306（4）,β=82.814（4）,γ=71.349（4）°,Z=1,V=814.9（3）3,Dc=1.735 g/cm3,μ（MoKα）=6.007 mm-1,F（000）=410,R=0.0307 and wR=0.0787.The bismuth ion and six chlorine ions construct a distorted octahedral configuration.The three-dimensional supramolecular network is built from electrostatic attractions,hydrogen bonds and π-π interaction between the BiCl6 anion,Cl anion and [2-（2-pyridyl）benzimidazoleH2] cation.The photoluminescence spectroscopy study shows that the title compound has a blue fluorescent emission at 450 nm in the solid state.
基金supported by the Natural Science Foundation of Fujian Province (2007HZ0001-1, 2009HZ0004-1, 2009HZ0006-1 and 2006L2005)
文摘The reactions of SbCl3 and HgCl2 with 2-（3-pyridyl）benzimidazole （PyBIm） in solution acidified with HCl have been investigated. The PyBIm ligands are protonated into 2-（3-pyridinio）benzimidazolium （H2PyBIm） cations and the corresponding metal ions are bonded with chloride atoms into coordination anions, forming two new coordination compounds, namely, （H2PyBIm）（SbCl5） 1 and （H2PyBIm）2（Hg2Cl8） 2. Both compounds were characterized by X-ray crystallography. Crystal data for 1： triclinic, space group P1^- with a = 5.7030（7）, b = 9.0625（11）, c = 16.5929（18） A, α = 91.808（7）°, β = 93.234（6）, γ = 99.216（7）°, C12H11N3SbCl5, Mr = 496.24, V = 844.44（17） A^3, Z = 2, Dc = 1.952 g/cm^3, μ（MoKα） = 2.419 mm^-1, F（000） = 480, the final R = 0.0496 and wR = 0.1382 for 3433 observed reflections （I 〉 2σ（I））. Crystal data for 2： monoclinic, space group P21/c with a = 7.8061（5）, b = 15.8127（9）, c = 12.2435（9） , β = 91.955（4）o, C24H22N6Hg2Cl8, Mr = 1079.26, V = 1510.40（17） 3, Z = 2, Dc = 2.373 g/cm3, μ（MoKα） = 10.889 mm-1, F（000） = 1008, the final R = 0.0293 and wR = 0.0562 for 2854 observed reflections （I 〉 2σ（I））. X-ray diffraction analysis reveals that the antimony（III） is five-coordinated, exhibiting a slightly distorted square-pyramidal coordination geometry; while in 2, a dimeric [Hg2Cl8]^4-anion consists of two trigonal bipyramids sharing two common edges. The organic cations and coordination anions are connected into a one-dimensional belt and a two-dimensional sheet through N-H···Cl hydrogen bonding interactions in compounds 1 and 2, respectively; both are further aggregated into 3D frameworks by strong π-π contacts.
基金supported by the research grant of Phytochemistry Key Laboratory of Shaanxi Province(No.11JS006,11JS007)the Scientific Research Fund of shaanxi Provincial Education Department(No.11JK0603)
文摘A double-T-shaped ligand （H4BPTC） and bis（2-benzimidazole）alkanes as the spacers have been firstly used to direct the assembly of a 2D coordination polymer with wavy parquet network topology, [Zn（BPTC）0.5（H2C2EIm）（H2O）]n （1, C24H18ZnN4O5, Mr = 507.79, H4BPTC = biphenyl-3,3＇,4,4＇-tetracarboxylic acid, H2C2EIm = 2,2＇-（1,2-ethanediyl）-bis（1H-benzi- midazole）, which was determined by single-crystal X-ray diffraction analysis. The crystal belongs to the monoclinic system, space group P21/n with a = 1.1844（5）, b = 1.4019（5）, c = 1.4026（5） nm, β = 108.359（5）°, V = 2.2104（15） nm3, Z = 4, Dc = 1.526 g/cm3, μ（MoKα） = 1.156 mm-1, F（000） = 1040, S = 1.038, the final R = 0.0427 and wR = 0.0793 for 3834 reflections with I 2σ（I）. The compound units are linked through BPTC ligands into a wavilness parquet 2D layer and further connected into a 3D framework via π-π packing interactions between the adjacent H2C2EIm ligands and weak N-H…O hydrogen bonding between uncoordinated carboxylate and the nitrogen atoms of H2C2EIm as well as the free water molecules.
文摘A convenient method to synthesize substituted 2 (2' hydroxyphenyl) benzimidazoles is reported. Six title compounds have been synthesized by the reaction of salicylic acid and 4 substituted o phenylenediamine in the presence pyridine POCl 3 . Three compounds were tested as plant virucide against tobacco mosaic virus and they exhibited some activities.
文摘<span style="font-family:Verdana;">A series of novel substituted benzimidazole </span><b><span style="font-family:Verdana;">(7a</span></b><b><span style="font-family:;" "=""> </span></b><b><span style="font-family:Verdana;">-</span></b><b><span style="font-family:;" "=""> </span></b><b><span style="font-family:Verdana;">n)</span></b><span style="font-family:Verdana;"> derivatives w</span><span style="font-family:Verdana;">ere</span><span style="font-family:;" "=""><span style="font-family:Verdana;"> synthesized and characterized by </span><sup><span style="font-family:Verdana;">1</span></sup><span style="font-family:Verdana;">H, </span><sup><span style="font-family:Verdana;">13</span></sup><span style="font-family:Verdana;">C Nuclear Magnetic Resonance (NMR) spectra and High Resolution Mass Spectrometry (HRMS). The substitution w</span></span><span style="font-family:Verdana;">as</span><span style="font-family:;" "=""><span style="font-family:Verdana;"> done in position -1 and -2 by appropriate groups. These compounds are obtained by N-alkylation reaction with thiomethyl-1</span><i><span style="font-family:Verdana;">H</span></i><span style="font-family:Verdana;">-benzimidazole intermediates </span><b><span style="font-family:Verdana;">(5a</span></b></span><b><span style="font-family:;" "=""> </span></b><b><span style="font-family:Verdana;">-</span></b><b><span style="font-family:;" "=""> </span></b><b><span style="font-family:Verdana;">g)</span></b><span style="font-family:;" "=""><span style="font-family:Verdana;">. Design of intermediates </span><b><span style="font-family:Verdana;">(5a</span></b></span><b><span style="font-family:;" "=""> </span></b><b><span style="font-family:Verdana;">-</span></b><b><span style="font-family:;" "=""> </span></b><b><span style="font-family:Verdana;">g)</span></b><span style="font-family:;" "=""><span style="font-family:Verdana;"> was made by condensation reaction between 2-methylbenzimidazole thiourunium salt </span><b><span style="font-family:Verdana;">(3)</span></b><span style="font-family:Verdana;"> and functionalized halides </span><b><span style="font-family:Verdana;">(4)</span></b><span style="font-family:Verdana;"> in the presence of sodium hydroxide (NaOH). Among the </span><span style="font-family:Verdana;">twenty-one compounds synthesized, ten were evaluated for their antimi</span><span style="font-family:Verdana;">crobial activity on three bacterial strains namely: </span><i><span style="font-family:Verdana;">Escherichia</span></i> <i><span style="font-family:Verdana;">coli</span></i><span style="font-family:Verdana;"> ATCC 25922, </span><i><span style="font-family:Verdana;">Staphylococcus</span></i> <i><span style="font-family:Verdana;">aureus</span></i><span style="font-family:Verdana;"> ATCC 25923 and </span><i><span style="font-family:Verdana;">Pseudomonas</span></i> <i><span style="font-family:Verdana;">aeruginosa</span></i><span style="font-family:Verdana;"> ATCC 27853. Only </span><i><span style="font-family:Verdana;">E.</span></i> <i><span style="font-family:Verdana;">coli</span></i><span style="font-family:Verdana;"> ATTC 25922 was susceptible to the synthesized derivatives </span><b><span style="font-family:Verdana;">5g</span></b><span style="font-family:Verdana;">, </span><b><span style="font-family:Verdana;">7f</span></b><span style="font-family:Verdana;"> and </span><b><span style="font-family:Verdana;">7h</span></b><span style="font-family:Verdana;"> with a significant antibacterial activity (CMI </span></span><span style="font-family:Verdana;">is </span><span style="font-family:Verdana;">between 250 and 500 μg/mL)</span><span style="font-family:Verdana;">.</span>
文摘On the base of benzimidazole and benzofuran containing heterocyclic system, several derivatives with expected biological activity were synthesized. 2,3-diaminodibenzofuran was the primary substance. Adding various cyclic agents, 2-phenil was got, 2-（o-chlorophenil）, 2-（o-oxyphenil）, 2-chlorometyl- and 2-hydroximethyl-3H-benzo[b[furo（3,2-f] benzimidazoles. The aforementioned substances were characterized by IR and NMR spectroscopy.
文摘A fast, high efficiency and environmentally friendly procedure for the synthesis of 2-aryl benzim-idazole derivatives has been reported. Reaction between 1,2-phenylenediamine derivatives and arylidene malononitrile under aqueous media and also solvent-free conditions generates 2-aryl benzimidazole derivatives with a high yield.
文摘A new method of synthesis of 2-(1,2-diferrocenylvinyl)benz- and azabenzimidazoles (3a-f), (4a-f) and 1’H,3’H(Me)-spiro-[(aza)benzimidazoline-2’,3-(1,2-diferrocenylcyclopropenes)] (5a-f) via reactions of diferrocenyl(methylsulfanyl)cyclopropenylium iodide (1) with aromatic o-diamines (2a-f) in the presence of Et3N (80°C - 82°C) is described. The structures of the resultant compounds are established using IR, 1H and 13C NMR spectroscopy, mass spectrometry and elemental analysis. The structure of one compound, cis-2-(1,2-diferrocenylvinyl)-1-methylbenzimidazole (3b), is confirmed by X-ray diffraction analysis. The electrochemical properties of compounds 3a, 3b, 3d and 5f are investigated using cyclic square wave voltammetry. Two electrochemical processes (I-II), attributed to oxidation of the ferrocene moieties, and the values of E0’(I), E0’(II), DE0’(II-I) and comporportionation constant Kcom are reported. The bioactivities of seven compounds 3a, 3c-f, 5d, 5f are evaluated. Compound 5f is the most active compound with a modest cytotoxic activity against six human cancer cell lines: U-251 (glioma), PC-3 (prostate cancer), K-562 (leukemia), HCT-15 (colon cancer), MCF-7 (breast cancer) and SKLU-1 (lung cancer).
基金supported by the research grant of Phytochemistry Key Laboratory of Shaanxi Province (No.11JS006,11JS007)the Scientific Research Fund of shaanxi Provincial Education Department (No.11JK0603)
文摘A new cadmium（Ⅱ） nitrite complex Cd2（H2C3PIm）2（BDC）（NO2）2（1,H2C3PIm = 2,2＇-（1,3-propanediyl）bis（1H-benzimidazole）,H2BDC = 1,4-benzenedicarboxylic acid） has been synthesized by solvothermal reaction in formamide,and its structure（C42H36Cd2N10O8,Mr = 1033.61） was determined by single-crystal X-ray diffraction analysis.The crystal belongs to the monoclinic system,space group P21/n with a = 0.9859（5）,b = 0.8936（5）,c = 2.3188（5） nm,β = 97.576（5）°,V = 2.025（16） nm3,Z = 2,Dc = 1.695 g/cm3,μ（MoKα） = 1.118 mm-1,F（000） = 1036,S = 1.017,the final R = 0.0304 and wR = 0.0752 for 3761 reflections with I 〉 2σ（I）.The centrosymmetric complex 1 contains a dimer in which two distorted octahedral Cd（II） centers are bridged by BDC ligand and chelated by H2C3PIm.The units of the complex are linked via weak N-H···O hydrogen bonds between the nitrito and the BDC ligands,leading to the formation of a 1D zigzag chain along the b axis.The π-π packing interactions contribute to the formation of a three-dimensional supramolecular architecture.The complex exhibits strong photoluminescence at room temperature.
基金supported by the National Natural Science Foundation of China(No.21342006)the Program for Innovative Research Team of the Ministry of Education of China(No.IRT_14R36)
文摘In order to discover the novel anti-tumor agents, a series of 2-[（pyridin-2-yl）methylthio]-1 H-benzimidazole derivatives were designed and synthesized, and the structures were characterized by IR, MS, and proton NMR. 2-[（3,4-Dimethoxypyridin-2-yl）methylthio]-1 Hbenzimidazole was investigated with X-ray crystallography, and the molecule is in orthorhombic system, space group P212121, with a = 9.1828（16）, b = 11.625（2）, c = 13.463（2） ？, Z = 4, R = 0.0231 and wR = 0.0596. The antitumor activities of target compounds were evaluated against human liver cancer cell line HepG2, and human liver normal cell line HL7702 using MTT assay. The target compounds have demonstrated weak or moderate anti-tumor activity against HepG2, while all the target compounds exhibit no cytotoxic effects on HL7702.
基金This work was financially supported by the National Natural Science Foundation of China(20171005)
文摘Dimethylaminophenyl)-5-fluoro-6-(morpholin-4-yl)-1H-benzimidazole(1) has been synthesized and characterized by H-NMR, MS and elemental analysis. UV-Vis spectra of the 1 aqueous solutions at different pH values reveal that compound 1 can combine three protons. Its three protonation constants are determined by spectrophotometry and calculated by non-linear least squares. The results of steady-state fluorescence measurements indicate that a special interaction occurs between compound 1 and calf thymus DNA, of which the binding constant, Kb, is (2.30 ± 0.10)×l04 L/mol. Compound 1 in the concentration range of 10-8 to 1.2×10-6 mol/L could be used for quantitative determination of DNA.
文摘The Iead compound of substituted 2-(4-hydroxyphenyl)benzimidazol were modified by phos-phorylation sulfonation and carboxymethylation. The henzimldazoloamidophosphate (6) (7) have better activi-ty against tobacco mosaic virus (TMV). The benzimldazolophenoxyacetic acid, phenoxysuIfonic acid c0ntaining tri flu0r0methyl, and nitro gr0up have 77% ~85% efflclency f0r wheat rust disease.
基金Supported by the National Natural Science Foundation of China(No.20771082)the Natural Science Foundation of Tianjin Municipality, China(No.09JCYBJC05800)the Educational Commission of Tianjin Municipality, China (No.20080509)
文摘Three sulfhydryl-reactive fluorescent probes, which contain 2-（1H-benzoimidazol-2-yl）-phenol and maleimide group, were synthesized and their structures were characterized by IR and ^1H NMR. Their photo-physical properties and the specificity to sulfhydryl group in the 2-mercapto-ethanol as well as the L-cysteine adducts were indicated by fluorescence intensity. Preliminary tests revealed that the probes could react selectively with the cysteine molecules, suggesting that these probes might be generally useful in biomedical researches.
