6468-35-5Relevant academic research and scientific papers
N-substituted benzimidazole acrylonitriles as in vitro tubulin polymerization inhibitors: Synthesis, biological activity and computational analysis
Perin,Hok,Be?,Persoons,Vanstreels,Daelemans,Vianello,Hranjec
, (2020/12/02)
We present the design, synthesis and biological activity of novel N-substituted benzimidazole based acrylonitriles as potential tubulin polymerization inhibitors. Their synthesis was achieved using classical linear organic and microwave assisted techniques, starting from aromatic aldehydes and N-substituted-2-cyanomethylbenzimidazoles. All newly prepared compounds were tested for their antiproliferative activity in vitro on eight human cancer cell lines and one reference non-cancerous assay. N,N-dimethylamino substituted acrylonitriles 30 and 41, bearing N-isobutyl and cyano substituents placed on the benzimidazole nuclei, showed strong and selective antiproliferative activity in the submicromolar range of inhibitory concentrations (IC50 0.2–0.6 μM), while being significantly less toxic than reference systems docetaxel and staurosporine, thus promoting them as lead compounds. Mechanism of action studies demonstrated that two most active compounds inhibited tubulin polymerization. Computational analysis confirmed the suitability of the employed benzimidazole-acrylonitrile skeleton for the binding within the colchicine binding site in tubulin, thus rationalizing the observed antitumor activities, and demonstrated that E-isomers are active substances. It also provided structural determinants affecting both the binding position and the matching affinities, identifying the attached NMe2 group as the most dominant in promoting the binding, which allows ligands to optimize favourable cation???π and hydrogen bonding interactions with Lys352.
Synthesis, computational analysis, and antiproliferative activity of novel benzimidazole acrylonitriles as tubulin polymerization inhibitors: Part 2
Be?, Anja,Daelemans, Dirk,Hok, Lucija,Hranjec, Marijana,Persoons, Leentje,Vanstreels, Els,Vianello, Robert
, (2021/11/01)
We used classical linear and microwave-assisted synthesis methods to prepare novel N-substituted, benzimidazole-derived acrylonitriles with antiproliferative activity against several cancer cells in vitro. The most potent systems showed pronounced activit
N, O-Bidentate ligand-tunable copper(II) complexes as a catalyst for Chan-Lam coupling reactions of arylboronic acids with 1 H-imidazole derivatives
Jia, Xuefeng,Peng, Pai
, p. 8984 - 8988 (2018/12/10)
An efficient procedure for Chan-Lam coupling reactions of arylboronic acids with 1H-imidazole derivatives using N,O-bidentate ligand-tunable copper(ii) complexes as a catalyst under base-free conditions has been developed. This protocol features mild reac
Synthesis, crystal structure and spectroscopic study of novel benzimidazoles and benzimidazo[1,2-a]quinolines as potential chemosensors for different cations
Hranjec, Marijana,Horak, Ema,Tireli, Martina,Pavlovi?, Gordana,Karminski-Zamola, Grace
, p. 644 - 656 (2012/11/07)
In this manuscript the synthesis, crystal structure, spectroscopic characterization and titration with several metal chloride salts of novel E-3-phenyl-2-(1-phenylbenzimidazol-2-yl)acrylonitriles and 5- phenylbenzimidazo[1,2-a]quinoline derivatives are described. All compounds were characterized by means of 1H, 13C NMR, MS, UV/Vis and fluorescence spectroscopy. Crystal and molecular structures of E-3-(4-nitrophenyl)-2-(1-phenyl-benzimidazol-2-yl)acrylonitrile and 5-phenylbenzimidazo[1,2-a]quinoline-6-carbonitrile were determined by single-crystal X-ray diffractometry. The molecular assembly is characterized by the C-H···O and C-H···N intermolecular hydrogen bonds in E-3-(4-nitrophenyl)-2-(1-phenyl-benzimidazol-2-yl) acrylonitrile and 5-phenylbenzimidazo[1,2-a]quinoline-6-carbonitrile, respectively. Spectroscopic characterization of the prepared compounds was performed by using UV/Vis and fluorescence spectroscopy in ethanol. In order to determine a selectivity towards a variety of cations, to explore their use as potential chemosensors, the amino substituted 5-phenylbenzimidazo[1,2-a] quinoline-6-carbonitrile was chosen for a titration with metal chloride salts using fluorescence spectroscopy. The fluorescence intensity significantly increased upon addition of Zn2+ and Ag+ cations while decreased by addition of Mn2+, Co2+, Cu2+, Hg2+, Li+ and Fe3+ cations.
SYNTHESIS OF CYANO OXIMES BASED ON AZOLES AND AZINES AND THE EFFECT OF THEIR PROTON-ACCEPTING CHRACTERISTICS ON THE STABILITY OF THE COMPLEXES OF THE LIGANDS WITH THE Fe(II) ION
Chernov'yants, M. S.,Gus'kova, T. V.,Chernoivanova, T. M.,Bagdasarov, K. N.,Tsupak, E. B.
, p. 1993 - 1997 (2007/10/02)
In the series of ligand systems based on ?-deficient azoles and azines with a hydroxyiminocyanomethyl complexing group at the α position to the pyridine-type nitrogen atom the basicity of the heterocyclic nitrogen atom decreases during benzannelation.A comparative assesment was made of the complexing capacity of cyano oximes and the stability of their chelate compounds with the Fe(II) ion.
