5999-14-4Relevant academic research and scientific papers
bis-(1H-Benzimidazol-2-yl)-methanone: New preparation method, crystal structure, vibrational spectroscopy and DFT calculations
Miranda, Fabio da Silva,Menezes, Fabrício Gava,Vicente, Juliano,Bortoluzzi, Adailton J.,Zucco, César,Neves, Ademir,Gon?alves, Norberto Sanches
, p. 1 - 9 (2009)
This study reports a new preparation of bis-(1H-benzimidazol-2-yl)-methanone, 3, an interesting compound prepared by the oxidation of bis-(1H-benzimidazol-2-yl)-methane using two methods: (i) Fe(II)/O2 in ethanol-water and (ii) hydrogen peroxide in acetic acid. Products of both methodologies were properly characterized by elemental analysis, IR, Raman, (1H and 13C) NMR and X-ray crystallography. DFT calculations [B3LYP/6-31+G(d,p)] also showed good agreement between the theoretical and experimental values of optimized and X-ray structures as well as between the vibrational and NMR spectroscopy. The study of the conformational dynamics of 3 found a low energy barrier (0.41 kcal mol-1) between the two conformations in the DMSO phase.
Polymerization and copolymerization of olefins and acrylates by bis(benzimidazole) copper catalysts
Stibrany, Robert T.,Schulz, Donald N.,Kacker, Smita,Patil, Abhimanyu O.,Baugh, Lisa S.,Rucker, Steven P.,Zushma, Stephen,Berluche, Enock,Sissano, Joseph A.
, p. 8584 - 8586 (2003)
CuBBIM/MAO is a highly versatile catalyst system that homopolymerizes ethylene and acrylates and, more significantly, induces ethylene/acrylate copolymerization. This new system is remarkable in spanning homopolymerization space broadly, while still enabling copolymerization of these traditionally transition-metal-catalyzed incompatible monomer classes.
STRUCTURAL FEATURES OF CADMIUM(II) COMPLEXES WITH BIS(BENZIMIDAZOL-2-YL)METHANE
Adonin, S. A.,El’tsov, I. V.,Lider, E. V.,Smirnova, K. S.,Sukhikh, T. S.
, p. 718 - 726 (2021/06/21)
Abstract: A series of cadmium(II) coordination compounds with bis(benzimidazol-2-yl)methane (L) is synthesized. Single crystals are obtained, and molecular and crystal structures of [Cd4(L)4Cl6(EtOH)0.77(H2O)1.23] [CdCl4]·H2O·5EtOH, [Cd(L)I2], and [Cd(L)2(EtOH)2][Cd(L)(NO3)3]2·6EtOH complexes are determined. According to the single crystal X-ray diffraction analysis, the organic ligand has a bidentate cyclic coordination. Distinctions in the structures of the compounds depending on the anion present are observed. The [Cd(L)I2] complex is mononuclear with cadmium ions are in the tetrahedral environment. Cadmium chloride and nitrate complexes are cationic-anionic with cadmium ions in different environments, and their coordination numbers vary in the range of 4-7.
Head-to-head bisbenzazole derivatives as antiproliferative agents: design, synthesis, in vitro activity, and SAR analysis
Ersan, Ronak Haj,Alagoz, Mehmet Abdullah,Ertan-Bolelli, Tugba,Duran, Nizami,Burmaoglu, Serdar,Algul, Oztekin
, p. 2247 - 2259 (2020/06/27)
Abstract: In the present work, a series of bisbenzazole derivatives were designed and synthesized as antiproliferative agents. The antiproliferative activity of these compounds was investigated using MTT assay. Bisbenzazole derivatives showed significant antiproliferative activity against all the four tested cancer cell lines. Among the various bisbenzazole derivatives, bisbenzoxazole derivatives exhibited the most promising anticancer activity followed by bisbenzimidazole and bisbenzothiazole derivatives. All the derivatives were found to be less toxic as compared to methotrexate (positive control) in normal human cells, indicating selective and efficient antiproliferative activity of these bisbenzazole derivatives. The structure–activity relationships of heteroaromatic systems and linkers present in bisbenzazole derivatives were analyzed in detail. In silico ADMET prediction revealed that bisbenzazole is a drug-like small molecule with a favorable safety profile. Compound 31 is a potential antiproliferative hit compound that exhibits unique cytotoxic activity distinct from methotrexate. Graphic abstract: Twenty-one bisbenzoxazole derivatives have been designed synthesized and evaluated to be an antiproliferative activity against four human tumor cell lines.[Figure not available: see fulltext.]
Bisbenzimidazole Derivatives as Potential Antimicrobial Agents: Design, Synthesis, Biological Evaluation and Pharmacophore Analysis
Ersan, Ronak Haj,Bolelli, Kayhan,Gonca, Serpil,Dogen, Aylin,Burmaoglu, Serdar,Algul, Oztekin
, p. 149 - 158 (2021/05/13)
In an attempt to design and synthesize a potent class of antimicrobials, 1,2-phenylenediamine derivatives were reacted with various aliphatic and heteroaliphatic dicarboxylic acids to generate a small library of 26 head-to-head bisbenzimidazole compounds (16 – 42) using the polyphosphoric acid method. These compounds were screened for their antibacterial activity and their antifungal activity. Compound 25 showed maximum potency against both Gram-positive and Gram-negative bacterial strains with minimum inhibitory concentration (MIC) values in the range of 7.81 – 31.25 μg/mL. In particular, it showed the maximum MIC values of 7.81 μg/mL against Gram-negative bacteria, which was four-fold more active than the standard drug ampicillin (MIC = 32.25 μg/mL). Compound 19 was found to be the most active against S. aureus with a MIC value of 3.90 μg/mL, whereas the remaining compounds showed only low-to-moderate activity. Furthermore, all compounds exhibited low activity against all fungal strains in comparison to the standard drug fluconazole. I addition, pharmacophore hypotheses were generated to analyze structure–activity relationships between the molecular structures and antimicrobial activities on E. coli. This pharmacophore model can be useful in order to design new antimicrobial drugs. It can be suggested that the substitution of a phenyl ring at the 5/6 and 5′/6′ positions in symmetric bisbenzimidazole derivatives produces compounds with promising antimicrobial activity.
An efficient synthesis of novel di-heterocyclic benzazole derivatives and evaluation of their antiproliferative activities
Algul, Oztekin,Ersan, Ronak Haj,Alagoz, Mehmet Abdullah,Duran, Nizami,Burmaoglu, Serdar
, p. 6926 - 6938 (2020/08/13)
A series of unsymmetrical nine di-heterocyclic compounds of benzazole derivatives were synthesized at one step via cyclization reaction. The compounds evaluated for in?vitro cytotoxic activity against A549, A498, HeLa, and HepG2 cancer cell lines. The biological evaluation results show that 23, 26 and 29 exhibit better activity against HepG2 and HeLa cancer cell lines. Compound 23 also showed good activity against A549, and A498 cancer cell lines. The analogs were further performed molecular docking studies against human cytochrome P450 2C8 monooxygenase enzyme, calculated some theoretical quantum parameters, ADMET descriptor and molecular electrostatic potential analysis. The strategy applied in this research work may act as a perspective for the rational design of potential anticancer drugs. Communicated by Ramaswamy H. Sarma.
Zr(IV) complexes of some heterocyclic ligands: Synthesis, characterization, and ethylene polymerization activity
Elagab, Hamdi Ali
, p. 742 - 761 (2016/11/09)
Thirty-one complexes of bis-(benzimidazole, benzothiazole, and benzoxazole) compounds with Zr(IV) metal centers were synthesized, characterized, activated with methylaluminoxane (MAO), and then tested for catalytic ethylene polymerization. The activities of the various catalysts were found to be functions of the heteroatoms in the ligand frameworks and the structure around the active metal center. The highest activity was obtained with 38/MAO (424 kg E/mol cat. h). The produced polyethylenes showed high molecular weights (41/MAO, 1.9 × 106 g/mol) and broad molecular weight distributions (38/MAO, Mw = 9.64 × 105 g/mol, PD = 23). This could result from different interactions of the MAO counter ion with the heteroatoms of the catalyst ligand generating different active sites.
Ti (IV) complexes of some heterocyclic ligands synthesis, characterization and ethylene polymerization activity
Elagab, Hamdi Ali
, p. 681 - 700 (2016/05/09)
31 complexes of bis - (benzimidazole, benzothiazole and benzoxazole) compounds with Ti (IV) metal centers were synthesized, characterized, activated with methylalumoxane (MAO) and then tested for catalytic ethylene polymerization. The activities of the various catalysts were found to be functions of the hetero atoms in the ligand frameworks. The highest activity was obtained with 39/MAO (573 kg PE/mol cat. h). The produced polyethylenes showed high molecular weights (up to 1.5 × 106 g/mol) and broad molecular weight distributions (PD = 65). This could result from different interactions of the MAO counterion with the heteroatoms of the catalyst ligand generating different active sites.
Structure-property-relationship studies with ethylene polymerization catalysts of Ti, Zr and V containing heterocyclic ligands
Elagab, Hamdi Ali,Alt, Helmut G.
, p. 26 - 35 (2015/09/01)
21 complexes of bis(benzimidazolyl, benzothiazolyl and benzoxazolyl)methane compounds with Zr(IV), Ti(IV), V(III) metal centers were synthesized, characterized, activated with methylalumoxane (MAO) and then tested for catalytic ethylene polymerization. The activities of the various catalysts were found to be functions of the hetero atoms in the ligand frameworks. The methylene moiety as bridging unit of the two heterocyclic ring systems gave higher catalyst activities than the corresponding 1,2-ethylidene derivatives indicating a strong influence of the bridging unit of the ligand on the catalyst activity. The activity of the catalyst system 10/MAO was investigated with different cocatalyst concentrations. The highest activity was obtained with 23/MAO (573 kg PE/mol cat h). The produced polyethylenes showed high molecular weights (up to 1.77·106 g/mol) and broad molecular weight distributions (up to PD = 64.5). This could result from different interactions of the MAO counterion with the heteroatoms of the catalyst ligand generating different active sites. These catalysts open an easy access to single-reactor multimodal polyethylene technology.
Expedient synthesis of benzimidazoles using amides
Kattimani, Pramod P.,Kamble, Ravindra R.,Meti, Gangadhar Y.
, p. 29447 - 29455 (2015/04/14)
In the present report an efficient, rapid, facile and inexpensive route for the synthesis of benzimidazoles using 1,2-arylenediamines and N,N-dimethylformamide in acidic medium under thermal/microwave condition is developed. This reaction was further explored with the different amides to afford a library of 2-substituted benzimidazoles. The advantage of the present synthetic method includes shorter reaction time, easy work up and excellent yields without using catalysts.
