2963-77-1Relevant articles and documents
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.
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.
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
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.
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.
Spectroscopic, computational and electrochemical studies on 2-(4-nitrophenyl)-1H-benzo[d]imidazole and its interaction with cationic surfactant cetyltrimethylammonium bromide
Datta, Arup,Roy, Sanjay,Mondal, Palash,Guin, Partha Sarathi
, p. 1058 - 1064 (2016)
2-(4-Nitrophenyl)-1H-benzo[d]imidazole (4-NBI) was prepared and characterized by experimental and computational methods. Electrochemical reduction of the compound was studied in dimethyl sulphoxide media which showed that the nitro group of the molecule undergoes quasireversible three-step reduction producing -NH2 while the imidazole nitrogen bonded to hydrogen undergoes an irreversible one-electron reduction. The electronic spectra were studied by TDDFT computational method and compared with the experimental results which corroborated each other excellently. The interaction of 4-NBI with the cationic surfactant cetyltrimethylammonium bromide (CTAB) was investigated in aqueous solution at physiological pH (7.4) by UV-Vis spectroscopy. By using different nonlinear fitting methods binding parameters were evaluated for 4-NBI - CTAB micelles interaction. The results showed that the electrostatic interaction plays a major role over hydrophobic interaction in the binding of 4-NBI to CTAB micelles. The electrostatic interaction has also an important role in the distribution of 4-NBI between CTAB micelle-water phases. Gibbs free energy for the binding and distribution of 4-NBI between the bulk aqueous medium and surfactant micelles was calculated.
Synthesis and in vitro evaluation of novel triazine analogues as anticancer agents and their interaction studies with bovine serum albumin
Singla, Prinka,Luxami, Vijay,Paul, Kamaldeep
, p. 59 - 69 (2016)
A novel series of triazine-benzimidazole analogs has been designed and synthesized for their in vitro anticancer activities. Four compounds (6, 16, 17 and 20) were identified as highly potent anticancer agents against 60 human cancer cell lines with GI50 in the nanomolar range. To improve the drug applications toward cancer cells, there is a need to couple these compounds to some carrier macromolecules. Following this approach, the interaction between triazine-benzimidazole analogues and bovine serum albumin (BSA) has been investigated with UV-Visible and fluorescence spectroscopic methods under physiological conditions. The observed fluorescence quenching indicates that these compounds could efficiently bind with BSA and be transported to the target site.
In vitro evaluation of the potential pharmacological activity and molecular targets of new benzimidazole-based schiff base metal complexes
Aragón-Muriel, Alberto,Liscano, Yamil,Morales-Morales, David,O?ate-Garzón, Jose,Polo-Cerón, Dorian,Ramírez-Apan, María Teresa,Robledo, Sara M.,Upegui, Yulieth
, (2021/07/02)
Metal-based drugs, including lanthanide complexes, have been extremely effective in clinical treatments against various diseases and have raised major interest in recent decades. Hence, in this work, a series of lanthanum (III) and cerium (III) complexes, including Schiff base ligands derived from (1H-benzimidazol-2-yl)aniline, salicylaldehyde, and 2,4-dihydroxybenzaldehyde were synthesized and characterized using different spectroscopic methods. Besides their cytotoxic activities, they were examined in human U-937 cells, primate kidney non-cancerous COS-7, and six other, different human tumor cell lines: U251, PC-3, K562, HCT-15, MCF-7, and SK-LU-1. In addition, the synthesized compounds were screened for in vitro antiparasitic activity against Leishmania braziliensis, Plasmodium falciparum, and Trypanosoma cruzi. Additionally, antibacterial activities were examined against two Gram-positive strains (S. aureus ATCC 25923, L. monocytogenes ATCC 19115) and two Gram-negative strains (E. coli ATCC 25922, P. aeruginosa ATCC 27583) using the microdilution method. The lanthanide complexes generally exhibited increased biological activity compared with the free Schiff base ligands. Interactions between the tested compounds and model membranes were examined using differential scanning calorimetry (DSC), and interactions with calf thymus DNA (CT-DNA) were investigated by ultraviolet (UV) absorption. Molecular docking studies were performed using leishmanin (1LML), cruzain (4PI3), P. falciparum alpha-tubulin (GenBank sequence CAA34101 [453 aa]), and S. aureus penicillin-binding protein 2a (PBP2A; 5M18) as the protein receptors. The results lead to the conclusion that the synthesized compounds exhibited a notable effect on model membranes imitating mammalian and bacterial membranes and rolled along DNA strands through groove interactions. Interactions between the compounds and studied receptors depended primarily on ligand structures in the molecular docking study.
