4857-04-9Relevant articles and documents
Synthesis, crystal structure, and properties of the cadmium complex with 2,5-bis((benzoimidazol-2-yl)methylthio)-1,3,4-thiadiazole
Wen, Yong-Hong,Chen, Yu-Yan,Wen, Hui-Ling,Xie, Xing-Lei,Wang, Lei
, p. 2780 - 2792 (2012)
A cadmium complex, [Cd(L)2(CH3OH)2] ·(NO3)2 (L=2,5-bis((benzoimidazol-2-yl)methylthio)- 1,3,4-thiadiazole), was synthesized and characterized by elemental analysis, infrared spectra, single-crystal and powder X-ray diffraction, UV-Vis spectra, electrochemical, and fluorescence properties. Single-crystal X-ray structure analysis reveals that the complex crystallizes in the triclinic crystal system with P1 space group. The coordination geometry around cadmium is octahedral. Intermolecular hydrogen bonds result in the generation of a 1-D infinite chain structure. Both UV-Vis spectra and cyclic voltammetry studies show the Cd(II) complex could be used as a probe to distinguish ssDNA from dsDNA. Differential pulse voltammetry indicates the complex could be used to analyze quantitatively for DNA. The solid complex exhibits strong luminescence emission in the visible region at room temperature upon excitation with UV radiation.
Synthesis, anticancer activity and docking studies of N-phenyl-2-(2-((4-phenyl piperazin-1-yl) methyl)-1H-benzo [d] imidazol-1-yl) acetamides
Boddu, Lingaiah,Pagudala, Ashok Kumar,Gandamalla, Durgaiah,Balabadra, Saikrishna,Manga, Vijjulatha,Reddy Yellu, Narsimha,Subhashini
, p. 362 - 368 (2018)
A series of novel N-phenyl-2-(2-((4-phenyl piperazin-1-yl) methyl)-1H-benzo [d] imidazol-1-yl) acetamides (7a-o) have been synthesized in multiple steps with suitable reaction procedures and well characterized by various analytical techniques. All the synthesized compounds were evaluated for their in vitro anticancer activity against three human cancer cell lines includes human cervical carcinoma (HeLa), human breast carcinoma (MCF-7) and human embryonic kidney (HEK 293) cell lines at various concentrations. The results were shown in terms of percentage cell viability reduction and IC50values were compared against standard anti cancer drug doxorubicin. Among all the synthesized compounds, compound 7k has shown highest activity against HeLa and MCF-7. The compounds 7b, 7l, 7m, 7n and 7o also showed significant activity over HeLa and MCF-7. Furthermore, the structure and anticancer activity relationship was supported by molecular docking study of the active compounds against quinone reductase-2 (PDB ID 4ZVM) protein.
Synthesis, characterization, and antifungal activity of novel benzo[4,5]imidazo[1,2-d][1,2,4]triazine derivatives
Li, Ling-Xia,Jiao, Jian,Wang, Xiao-Bin,Chen, Min,Fu, Xin-Can,Si, Wei-Jie,Yang, Chun-Long
, (2018)
A series of novel fused heterocyclic compounds bearing benzo[4,5]imidazo[1,2-d][1,2,4] triazine 4a–4w were designed and conveniently synthesized via the intermediates 2-(halogenated alkyl)-1H-benzo[d]imidazoles 2a, 2b, and 2-((1-(substituted phenyl)hydrazinyl)alkyl)-1H-benzo[d] imidazoles 3a–3g. The structures of all target compounds were characterized by FT-IR, 1H NMR, 13C NMR, and EI-MS, of which, the structure of compound 4n was further determined by the single crystal X-ray diffraction. The crystal structure of 4n was crystallized in the triclinic crystal system, space group P1 with a = 9.033 (6), b = 10.136 (7), c = 10.396 (7), α = 118.323 (7)?, β = 91.750 (8)?, γ = 104.198 (7)?, Z = 2, V = 800.2 (9)3; total R indices: R1 = 0.0475, wR2 = 0.1284. The antifungal activity of title compounds 4a–4w in vitro against the phytopathogenic fungi Botrytis cinerea (B. cinerea), Rhizoctonia solani (R. solani) and Colletotrichum capsici (C. capsici) were evaluated, the bioassay results demonstrated that most of the title compounds exhibited obvious fungicidal activities at 50 μg/mL. This work indicated that benzo[4,5]imidazo[1,2-d][1,2,4]triazine derivatives could be considered as a new leading structure in searching for novel agricultural fungicides.
1-benzyl-2-(2,6-dichloroanilinomethyl)-1H-benzimidazole
Kendi, Engin,Oezbey, Sueheyla,Tuncbilek, Meral,Goeker, Hakan
, p. 854 - 856 (1998)
The benzimidazole ring of the title compound, C21H17Cl2N3, is planar and makes an angle of 98.38 (6)° with the phenyl ring of the benzyl substituent at N1. The molecules are joined together by C-H...N intermolecular hydrogen bonds.
Design, Synthesis, Antihyperglycemic Studies, and Docking Simulations of Benzimidazole-Thiazolidinedione Hybrids
Gutierréz-Hernández, Abraham,Galván-Ciprés, Yelzyn,Domínguez-Mendoza, Elix Alberto,Aguirre-Vidal, Yoshajandith,Estrada-Soto, Samuel,Almanza-Pérez, Julio César,Navarrete-Vázquez, Gabriel
, (2019)
A simple and cheap three-step procedure for the synthesis of three (5Z)-5-[3(4)-(1H-benzimidazol-2-ylmethoxy)benzylidene]-1,3-thiazolidine-2,4-diones has been described via a SN2 reaction of generally recognized as safe hydroxybenzaldehydes and 2-(chloromethyl)-1H-benzimidazole, followed by a Knoevenagel condensation with thiazolidine-2,4-dione in moderated yields. All the newly synthesized compounds were characterized using analytical and spectral studies. In vitro treatment on adipocytes with compounds increased the mRNA expression of two proteins recognized as strategic targets in diabetes: PPARγ and GLUT-4. In silico studies were conducted in order to explain the interaction binding mode of the synthesized compounds on PPARγ. In vivo studies confirmed that compounds 1-3 have robust antihyperglycemic action linked to insulin sensitization mechanisms. The present study provides three compounds with a promising antidiabetic action.
Synthesis, characterization and tumor inhibitory activity of a novel Pd(ii) complex derived from methanethiol-bridged (2-((1H-benzo[d]imidazol-2-yl)methylthio)-1H-benzo[d]imidazol-6-yl)(phenyl)methanone
Sunil Kumar,Krishnamurthy, Krishnamurthy,Bodke, Yadav D.,Malojirao, Vikas H.,Ravikumar Naik,Kandagalla, Shivananda,Prabhakar
, p. 790 - 806 (2019)
In this study, we designed a therapeutic active Pd(ii) complex with the new (2-((1H-benzo[d]imidazol-2-yl)methylthio)-1H-benzo[d]imidazol-5-yl)(phenyl)methanone ligand in good yield. The structure of the ligand and its Pd(ii) complex was characterized via IR, UV-visible, 1H-NMR, 13C-NMR, mass spectroscopy, TGA and powder XRD techniques. The spectral data of the Pd(ii) complex indicated the bidentate bonding mode for bis-benzimidazole and suggested a tetrahedral geometry for the metal complex. The in vitro antiproliferative effect of the BIPM ligand and Pd(ii) complex were tested against the MCF7, A549, Ehrlich ascites carcinoma (EAC) and Daltons lymphoma ascites (DLA) carcinoma cell lines. The metal complex exhibited excellent antiproliferative potency with a significant IC50 value of ～10 μm against the EAC cell line compared to the ligand alone with a value of ～17 μM. Further, the in vivo antitumor effect study on the Pd(ii) complex against a murine EAC tumor model system showed obvious extended survivability. The tumor inhibitory mechanism of the Pd(ii) complex is due to its antiangiogenic effect and promotion of apoptosis, as verified by DNA condensation and FACS analysis. The potential photo-induced binding mode on double-stranded calf thymus DNA and protein cleavage activity study on pBR322 DNA of the complex confirmed its apoptotic characteristics. The significant hypochromic shift due to the strong π-π stacking interaction between the metal complex and the base pairs of DNA was clearly shown by the intrinsic DNA binding constant, kb. The molecular docking study on the Pd(ii) complex interaction with DNA further confirmed its inhibition ability. The experimental results and drug-likeness properties of the Pd(ii) complex suggest its potential applications, which can be developed as a potent anticancer drug in the near future.
Design and synthesis of benzimidazole analogs endowed with oxadiazole as selective COX-2 inhibitor
Rathore, Ankita,Rahman, Mujeeb Ur,Siddiqui, Anees Ahamad,Ali, Abuzer,Shaharyar, Mohammad
, p. 923 - 935 (2014)
New molecules of benzimidazole endowed with oxadiazole were designed and synthesized from 2-(2- ((pyrimidin-2-ylthio)methyl)-1H-benzo[d]imidazol-1-yl)acetohydrazide as 1-((5-substituted alkyl/aryl- 1,3,4-oxadiazol-2-yl)methyl)-2-((pyrimidin-2-ylthio)methyl)-1H-benzimidazoles (5a-r ) with the aim to acquire selective cyclooxygenase (COX-2) inhibitor activity. The synthesized compounds were screened by in vitro cyclooxygenase assays to determine COX-1 and COX-2 inhibitory potency and the results showed that they had good-to-remarkable activity with an IC50 range of 11.6-56.1 μM. The most active compounds were further screened for their in vivo anti-inflammatory activity by using the carrageenaninduced rat paw edema model. In vitro anticancer activities of the hybrid compounds were assessed by the National Cancer Institute (NCI), USA, against 60 human cell lines, and the results showed a good spectrum. Compound 5l exhibited significant COX-2 inhibition with an IC50 value of 8.2 μ M and a percent protection of 68.4%. Compound 5b evinced moderate cytotoxicity toward the UO-31 cell line of renal cancer. A docking study was performed using Maestro 9.0, to provide the binding mode into the binding sites of the cyclooxygenase enzyme. Hopefully, in the future, compound 5l could serve as a lead compound for developing new COX-2 inhibitors.
Synthesis of new benzimidazole and phenylhydrazinecarbothiomide hybrids and their anticonvulsant activity
Siddiqui, Nadeem,Alam, Md. Shamsher,Ali, Ruhi,Yar, M. Shahar,Alam, Ozair
, p. 1390 - 1402 (2016)
A series of new benzimidazole derivatives (4a–p) were synthesized and evaluated for anticonvulsant activity in albino mice against two most adopted models, i.e. maximal electroshock seizure (MES)- and subcutaneous pentylenetetrazole (scPTZ)-induced seizures. Synthesized compounds were also screened for possible neurotoxicity using rotarod test. Among the synthesized compounds, 4p showed the most promising activity in MES and scPTZ screens, which was further subjected for oral activity in rats. At a dose of 30?mg/kg, it showed tremendous activity in the scPTZ screen. The acute toxicity study (LD50) of compounds showed that only two tested compounds 4f and 4m did not produce any mortality at any of the dose level. Molecular properties and pharmacokinetic parameters of the titled compounds were also determined using Lipinski’s rule of five. The promising results encourage future investigation on the rational modification of this nucleus for development of better compounds.
One-pot multicomponent synthesis of novel 2-(piperazin-1-yl) quinoxaline and benzimidazole derivatives, using a novel sulfamic acid functionalized Fe3O4 MNPs as highly effective nanocatalyst
Esam, Zohreh,Akhavan, Malihe,Bekhradnia, Ahmadreza
, (2020/10/27)
The immobilization of sulfonic acid on the surface of Fe3O4 magnetic nanoparticles (MNPs) as a novel acid nanocatalyst has been successfully reported. The morphological features, thermal stability, magnetic properties, and other physicochemical properties of the prepared superparamagnetic core–shell (Fe3O4@PFBA–Metformin@SO3H) were thoroughly characterized using Fourier transform infrared (FTIR), X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDS), field-emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), thermogravimetric analysis–differential thermal analysis (TGA-DTA), atomic force microscopy (AFM), dynamic light scattering (DLS), Brunauer–Emmett–Teller (BET), and vibrating sample magnetometer (VSM) techniques. It was applied as an efficient and reusable catalyst for the synthesis of 2-(piperazin-1-yl) quinoxaline and benzimidazole derivatives via a one-pot multiple-component cascade reaction under green conditions. The results displayed the excellent catalytic activity of Fe3O4@PFBA–metformin@SO3H as an organic–inorganic hybrid nanocatalyst in condensation and multicomponent Mannich-type reactions. The easy separation, simple workup, excellent stability, and reusability of the nanocatalyst and quantitative yields of products and short reaction time are some outstanding advantages of this protocol.
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.
