2963-77-1Relevant academic research and scientific papers
New Benzimidazoles and Their Antitumor Effects with Aurora A Kinase and KSP Inhibitory Activities
Abd El-All, Amira S.,Magd-El-Din, Asmaa A.,Ragab, Fatma A. F.,Elhefnawi, Mahmoud,Abdalla, Mohamed M.,Galal, Shadia A.,El-Rashedy, Ahmed A.
, p. 475 - 486 (2015)
A newly synthesized series of anticancer compounds comprising thiazolo[3,2-a]pyrimidine derivatives 6a-q bearing a benzimidazole moiety was produced via a one-pot reaction of N-(4-(1H-benzo[d]imidazol-2-yl)phenyl)-2-cyanoacetamide 5 with 2-aminothiazole and an appropriate aromatic aldehyde. Compound 7 was obtained via the reaction of 4-(1H-benzo[d]imidazol-2yl)benzenamide 1 with carbon disulphide and methyl iodide in the presence of concentrated aqueous solution of NaOH, then treated with o-phenylenediamine to give N-(4-1H-benzo[d]imidazol-2-yl)phenyl)-1H-benzo[d]imidazol-2-amine 8. The structures of the newly synthesized compounds were confirmed by analytical and spectroscopic measurements (IR, MS, and 1H NMR). The synthesized products were screened and studied for their in vitro antitumor activity against three human cancer cell lines (namely colorectal cancer cell line HCT116, human liver cancer cell line HepG2, and human ovarian cancer cell line A2780) and their Aurora A kinase and KSP inhibitory activities. All newly synthesized compounds revealed marked results comparable with the standard drug CK0106023. The compounds 6e and 6k of the thiazolopyrimidine derivatives were the most active compounds when tested against the three cell lines in comparison with the standard drug CK0106023, and showed potent dual KSP and Aurora A kinase inhibition.
Analgesic, anti-inflammatory, and antimicrobial activities of novel isoxazole/pyrimidine/pyrazole substituted benzimidazole analogs
Chikkula, Krishna Veni,Sundararajan, Raja
, p. 3026 - 3037 (2017)
From o-phenylenediamine and p-amino benzoic acid, several new 3-methylisoxazol-5(4H)-one/2-hydroxy/mercapto-6-methylpyrimidin-4(5H)-one/3-methyl-1-substituted-1H-pyrazol-5(4H)-one substituted benzimidazole derivatives 5–16 were synthesized through multi step synthesis based on hybrid approach. All test compounds were screened for its analgesic, anti-inflammatory, and in vitro antimicrobial activity by tail flick method, carrageenan induced foot paw edema method and agar streak dilution method, respectively. Most active compounds were examined for its ulcerogenicity by pylorus ligation method. The relationship between chemical structure and biological activities of the test compounds were discussed. Among various tested compounds, 4-(2-(4-(1H-benzimidazol-2-yl)phenyl)hydrazono)-1-(4-chlorophenyl)-3-methyl-1H-pyrazol-5(4H)-one 10 was found to be most potent compound. This compound showed 72% analgesic activity (20 mg/kg; second hour) and 67% protection in paw edema test (20 mg/kg; second hour) which are comparable with that of standard Diclofenac [69% analgesic activity (20 mg/kg; second hour) and 65% protection in paw edema test (20 mg/kg; second hour)]. In addition, compound 10 exhibited least ulcer index which is about 1/3 of the ulcer index of reference standard and showed good antibacterial and moderate antifungal activity.
Antitumor agents. 194. Synthesis and biological evaluations of 4-β- mono-, -di-, and -trisubstituted aniline-4'-O-demethyl-podophyllotoxin and related compounds with improved pharmacological profiles
Zhu,Guan,Tachibana,Bastow,Sung Jin Cho,Cheng H.-,Cheng,Gurwith,Lee
, p. 2441 - 2446 (1999)
As a continuation of our structure-activity relationship studies, several new 4-β-substituted 4'-O-demethyl-4-desoxypodophyllotoxins bearing mono-, di-, or trisubstituted anilines have been synthesized and evaluated as inhibitors of DNA topoisomerase II and tumor cell growth in tissue culture. Selected compounds were further evaluated as cytotoxic agents using a clonogenic survival assay. The target compounds include 4'-O-demethyl-4β- [(4''-(benzimidazol-2''-yl)anilino]-4-desoxypodophyllotoxin (21), 4'-O- demethyl-4β-(-)-(4'-camphanamido-anilino)-4-desoxypodophyllotoxin (25), 4- β-disubstituted-anilino-4'-demethyl-4-desoxypodophyllotoxins (18-20, 26), 4- α-disubstituted-anilino-4'-demethyl-4-desoxypodophyllotoxin (27), 4-β- trisubstituted-anilino-4'-demethyl-desoxypodophyllotoxin (22, 23), and 4'-O- demethyl-4β-[4'-(benzimidazol-2''-yl)amino]-4-desoxypodophyllotoxin (24). Among the target series, 19, 21, and 24 displayed significant growth inhibitory action against a panel of tumor cell lines including human epidermoid carcinoma of the nasopharynx (KB) and its etoposide-resistant (KB7B) and vincristine-resistant (vin20c KB) subclones, lung carcinoma (A549), human ileocecal carcinoma (HCT-8), human kidney carcinoma (CAKI-1), breast adenocarcinoma (MCF-7), and human malignant melanoma (SK-MEL-2) cells. Compounds 19, 21, 24, and 25 were 'cleavable-complex'-forming DNA topoisomerase II inhibitors with either improved or similar activity compared with the prototype drug etoposide (VP-16). Compound 21 was the most active analogue, being 10-fold more potent than etoposide in both cell killing and topoisomerase II inhibition in vitro assays. Using mouse models of antitumor activity, 21 was effective against (P388/0) leukemia but not against the growth of a (MCF7) mammary tumor.
Metal Actuated Ring Translocation Switches in Water
Yin, Hang,Rosas, Roselyne,Gigmes, Didier,Ouari, Olivier,Wang, Ruibing,Kermagoret, Anthony,Bardelang, David
, p. 3187 - 3191 (2018)
Among a series of metal ions in water, silver is the only one to remotely and reversibly switch cucurbit[7]uril (CB[7]) movements (translocation or uptake) on a rigid and linear three-station viologen-phenylene-imidazole (V-P-I) derivative, avoiding undesired pH actuation. 1H NMR, UV-vis spectroscopy, mass spectrometry, ITC, and modeling were combined to show that ring translocation or uptake along a molecular thread is possible in water by Ag+ as a metal stimulus.
Activation of - N=CH - bond in a Schiff base by divalent nickel monitored by NMR evidence
Chandrakala,Nanje Gowda,Murthy,Nagasundara
, p. 335 - 340 (2012)
The Schiff base, 2-salicylidene-4-aminophenyl benzimidazole in ethanol undergoes activation of -N=CH- bond by Ni2+ in the presence of ammonia or primary alkyl amine to produce nickel complexes of the formula Ni{o-C6H4(O)CH NR}2. n H2O [R=H, Me; n=0; R=Et, n=0.5] and 4-aminophenyl benzimidazole. The products have been identified by elemental analysis, magnetic susceptibility measurements and IR, ESR, mass and extensive NMR spectral studies. The possible mechanism for the activation of -N=CH - bond has also been proposed. Copyright
Synthesis, DNA binding and antibacterial activity of metal(II) complexes of a benzimidazole Schiff base
Mahmood, Khalid,Hashmi, Waleed,Ismail, Hammad,Mirza, Bushra,Twamley, Brendan,Akhter, Zareen,Rozas, Isabel,Baker, Robert J.
, p. 326 - 334 (2019)
The benzimidazole derivative (E)-2-((4-(1H-benzo[d]imidazol-2-yl)phenylimino)methyl)-4-bromo phenol and the corresponding Zn(II), Ni(II), Cu(II), and Pd(II) complexes were prepared. The synthesized ligand and complexes were fully characterized and the ligand structure confirmed by single crystal X-ray diffraction analysis. The ability of this compound and its complexes to bind to DNA was first investigated with DNA thermal denaturation experiments, in general showing weak interactions. Additionally, UV–Vis absorption spectroscopy was used to assess the binding to DNA and the corresponding binding constants (Kb) were calculated suggesting an intercalative mode of binding for the benzimidazole ligand. All compounds were screened for their antibacterial activity and the Ni(II) complex showed promising results against all bacterial strains (Gram positive and Gram negative) while the rest of the compounds showed activity against selective strains.
Crystal structures and biological activities of Mn (II) and Cd (II) complexes from an asymmetrical Schiff base ligand
Zhang, Jing-An,Li, Yu,Fan, Yan-Zhong,Zou, Xun-Zhong,Liu, Ya-Jie,Zhang, Li-Jie,Zheng, Sheng-Run
, p. 136 - 139 (2014)
The Mn(II) and Cd(II) complexes of an asymmetrical Schiff base ligand 4-(1H-benzimidazol-2-yl)-phenyl]-pyridin-4-methyl amine have been prepared by the method of diethyl ether diffusion. The structures of the complexes were identified by elemental analysis (EA), infrared spectra (IR) and single-crystal X-ray diffraction. It was revealed that complexes 1 and 2 were composed of discrete mononuclear structures, and formed schistose structures via two different kinds of hydrogen bonds. The antibacterial and antifungal activities of the ligand and two complexes were tested, which may provide useful information for the research and application in pharmaceutical chemicals.
A Topotactic Synthetic Methodology for the Synthesis of Nanosized MFI Zeolites with Hierarchical Structures
Li, Ang,Wang, Xue,Wang, Tao,Liu, Huali,Gao, Tunan,Fan, Meihong,Huo, Qisheng,Qiao, Zhen-An
, p. 12600 - 12606 (2018)
Much effort has been invested in the designed synthesis of zeolites with nanosized and hierarchical structures in recent decades, on account of increasing demands in practical applications, especially catalysis. Herein, a new topotactic synthetic strategy is demonstrated to synthesize nanosized and hierarchical zeolites in a one-step procedure. By using silica spheres as the adjustable amorphous precursors and tetrapropylammonium hydroxide as a structure-directing agent, effortless control of both size and porosity can be achieved in this system with no extra templates. With a simple hydrothermal process, hierarchical zeolite spheres can be modified with acid cites (Al species incorporated in the framework). Benefitting from its mesoporosity, palladium nanoparticles are incorporated into the nanosized hierarchical zeolite, which makes the materials suitable for use in a cascade catalysis reaction of benzimidazole derivatives, including independent acid catalysis and hydrogenation sites. The nanocomposites show exceptional activity and stability in catalysis and recycling reaction. This strategy can be developed into other versatile and practicable scaffolds for advanced zeolite catalytic nanoreactor systems.
Novel Mixed Complexes Derived from Benzoimidazolphenylethanamine and 4-(Benzoimidazol-2-yl)aniline: Synthesis, characterization, antibacterial evaluation and theoretical prediction of toxicity
Aroua, Lotfi M.
, p. 1266 - 1272 (2020)
Benzoimidazolphenylethanamine (BPE) has been synthesized using condensation reaction from o-phenyldiamine and L-phenylalanine. Some metal complexes have been synthesized from 4-(benzoimidazol-2-yl)aniline, benzoimidazolylphenylethanamine and cadmium(II), tin(II), copper(II) and nickel(II) metal in a molar ratio (1:1:1). All new metal complexes were characterized by spectroscopic data of FTIR, UV-visible electronic absorption, X-ray powder diffraction and thermal analysis. Spectra analysis of the mixed metal complexes showed the coordination of ligands to the metal ions via nitrogen atoms. The XRD powder showed that metal complexes have a monoclinic system. The preliminary tested in vitro antibacterial activities of Sn(II) complex was assayed against four bacterial isolates namely Micrococcus luteus, Staphylococcus aureus as Gram-positive, Pseudomonas aerugmosa and Escherichia coli.
Computational design, synthesis and evaluation of new sulphonamide derivatives targeting HIV-1 gp120
Vangala, Radhika,Sivan, Sree Kanth,Peddi, Saikiran Reddy,Manga, Vijjulatha
, p. 39 - 54 (2020)
Attachment of envelope glycoprotein gp120 to the host cell receptor CD4 is the first step during the human immunodeficiency virus-1 (HIV-1) entry into the host cells that makes it a promising target for drug design. To elucidate the crucial three dimensional (3D) structural features of reported HIV-1 gp120 CD4 binding inhibitors, 3D pharmacophores were generated and receptor based approach was employed to quantify these structural features. A four-partial least square factor model with good statistics and predictive ability was generated for the dataset of 100 molecules. To further ascertain the structural requirement for gp120-CD4 binding inhibition, molecular interaction studies of inhibitors with gp120 was carried out by performing molecular docking using Glide 5.6. Based on these studies, structural requirements were drawn and new molecules were designed accordingly to yield new sulphonamides derivatives. A water based green synthetic approach was adopted to obtain these compounds which were evaluated for their HIV-1 gp120 CD4 binding inhibition. The newly synthesized compounds exhibited remarkable activity (10-fold increase) when compared with the standard BMS 806. Further the stability of newly synthesized derivatives with HIV-1 gp120 was also investigated through molecular dynamics simulation studies. This provides a proof of concept for molecular modeling based design of new inhibitors for inhibition of HIV-1 gp120 CD4 interaction.
