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, 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.
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.
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.
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.
Design, synthesis, anticancer activity, and solid lipid nanoparticle formulation of indole-and benzimidazole-based compounds as pro-apoptotic agents targeting bcl-2 protein
Nagy, Manar I.,Darwish, Khaled M.,Kishk, Safaa M.,Tantawy, Mohamed A.,Nasr, Ali M.,Qushawy, Mona,Swidan, Shady A.,Mostafa, Samia M.,Salama, Ismail
, p. 1 - 37 (2021/02/16)
Cancer is a multifactorial disease necessitating identification of novel targets for its treat-ment. Inhibition of Bcl-2 for triggered pro-apoptotic signaling is considered a promising strategy for cancer treatment. Within the current work, we aimed to design and synthesize a new series of benzimidazole-and indole-based derivatives as inhibitors of Bcl-2 protein. The market pan-Bcl-2 inhibitor, obatoclax, was the lead framework compound for adopted structural modifications. The obatoclax’s pyrrolylmethine linker was replaced with straight alkylamine or carboxyhydrazine methylene linkers providing the new compounds. This strategy permitted improved structural flexibility of synthesized compounds adopting favored maneuvers for better fitting at the Bcl-2 major hydrophobic pocket. Anti-cancer activity of the synthesized compounds was further investigated through MTT-cytotoxic assay, cell cycle analysis, RT-PCR, ELISA and DNA fragmentation. Cytotoxic results showed compounds 8a, 8b and 8c with promising cytotoxicity against MDA-MB-231/breast cancer cells (IC50 = 12.69 ± 0.84 to 12.83 ± 3.50 μM), while 8a and 8c depicted noticeable activities against A549/lung adenocarcinoma cells (IC50 = 23.05 ± 1.45 and 11.63 ± 2.57 μM, respectively). The signaling Bcl-2 inhibition pathway was confirmed by molecular docking where significant docking energies and interactions with key Bcl-2 pocket residues were depicted. Moreover, the top active compound, 8b, showed significant upregulated expression levels of pro-apoptotic/anti-apoptotic of genes; Bax, Bcl-2, caspase-3,-8, and-9 through RT-PCR assay. Improving the compound’s pharmaceutical profile was undertaken by introducing 8b within drug-solid/lipid nanoparticle formulation prepared by hot melting homogenization technique and evaluated for encapsulation efficiency, particle size, and zeta potential. Significant improvement was seen at the compound’s cytotoxic activity. In conclusion, 8b is introduced as a promising anti-cancer lead candidate that worth future fine-tuned lead optimization and development studies while exploring its potentiality through in-vivo preclinical investigation.
Exploring electronic structure, and substituent effect of some biologically active benzimidazole derivatives: Experimental insights and DFT calculations
Mansour, Ahmed M.,Shehab, Ola R.
, (2020/08/11)
A series of (1H-benzimidazol-2-ylmethyl)-N-(4-phenyl)amine derivatives incorporating different electron-donating and withdrawing groups (X = 4[sbnd]OCH3 (1), 4[sbnd]CH3 (2), H (3), 4[sbnd]Cl (4), and 4[sbnd]Br (5)) on the para-position of the phenyl substituent was prepared, characterized and screened for their potential antimicrobial activity against some microbes. The substituent effect on the spectroscopic data (vibrational modes and NMR resonances) is well established by fitting with the Hammett constant. The unsubstituted derivative 4 exhibited comparable activity (MIC = 0.26 μM) to the standard tetracycline (MIC = 0.18 μM) against Staphylococcus aureus. Introduction of a substituent to the phenyl ring led to diminishing of the antibacterial activity. The substituent effect on the electron structure of 1–5 was investigated by TDDFT calculations. The acid dissociation constants of the ionizable NH group correlate well with Kubota's σ? parameter (R2 = 0.9196). The solvatochromism behavior of 1–5, in solvents of different polarity and hydrogen-bond tendency, was investigated by linear solvation–energy relationship equation analysis. Correlation between various quantum chemical descriptors, and antibacterial activity was carried out to verify a structural activity relation for this series of benzimidazole derivatives.
