- Exploring electronic structure, and substituent effect of some biologically active benzimidazole derivatives: Experimental insights and DFT calculations
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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.
- Mansour, Ahmed M.,Shehab, Ola R.
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- Light-activated cytotoxicity of dicarbonyl Ru(ii) complexes with a benzimidazole coligand towards breast cancer
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Reaction between [RuCl2(CO)2]n and 1H-benzimidazol-2-ylmethyl-(N-phenyl)amine ligands (LR) functionalized with various electron-donating and electron-withdrawing substituents on the phenyl ring (R = H, 4-CH3, 4-Cl, 4-COOCH3, and 3-COOCH3) afforded the dark-stable photoactivatable carbon monoxide prodrugs of the general formula [RuCl2(CO)2LR]. Release of the CO molecules from the Ru(ii) compounds was examined by monitoring the electronic and IR spectra upon illumination at 365 nm. A noticeable decrease in the intensities of the two characteristic ν(CO) modes for Ru(CO)II2 species, and the growth of two new bands for the mono-carbonyl species and free CO, were the main features of the photolysis profiles. The cytotoxicity of the complexes towards breast cancer (MCF-7) cells was assessed with and without illumination at 365 nm. All the complexes except that with a 4-COOCH3 group (IC50 = 45.08 ± 3.5 μM) are nontoxic under dark conditions. Upon illumination, all the compounds acquired cytotoxicity in the following order: H > 4-COOCH3 > 4-CH3 > 4-Cl > 3-COOCH3. Investigation of the cytotoxicity of the CO-depleted fragments showed that the light-induced cytotoxicity can be attributed to the liberated CO and CO-depleted metal fragments, including the liberated benzimidazole ligands.
- Farag, Ahmad M.,Ibrahim, Nourhan M.,Khaled, Rabaa M.,Mansour, Ahmed M.,Radacki, Krzysztof,Ragheb, Mohamed A.
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p. 15389 - 15399
(2021/11/17)
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- Benzimidazole derivative, benzothiophene derivative as well as preparation method and application of benzoimidazole derivative and benzothiophene derivative
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The invention provides a benzimidazole derivative and a benzothiophene derivative. The benzimidazole derivative and the benzothiophene derivative respectively have structures shown in a formula (I) and a formula (IV). Experimental results show that the benzimidazole derivative and the benzothiophene derivative provided by the invention have good anti-tumor activity and can be used for preparing related tumor disease treatment medicines.
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Paragraph 0046-0048; 0050-0053; 0074-0078
(2020/08/25)
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- Novel tertiary sulfonamide derivatives containing benzimidazole moiety as potent anti-gastric cancer agents: Design, synthesis and SAR studies
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With the expectation to find out new anti-gastric cancer agents with high efficacy and selectivity, a series of novel tertiary sulfonamide derivatives were synthesized and the anti-cancer activity was studied in three selected cancer cell lines (MGC-803, PC-3, MCF-7) in vitro. Some of the synthesized compounds could significantly inhibit the proliferation of these tested cancer cells and were more potent than the positive control (5-Fu). The structure-activity relationship of tertiary sulfonamide derivatives was explored in this report. Among the tested compounds, compound 13g containing benzimidazole moiety showed the best anti-proliferation activities against MGC-803 cells (IC50 = 1.02 μM), HGC-27 cells (IC50 = 1.61 μM), SGC-7901 (IC50 = 2.30 μM) cells as well as the good selectivity between the cancer and normal cells. Cellular mechanism studies elucidated compound 13g inhibited the colony formation of gastric cancer cell lines. Meanwhile, compound 13g arrested cell cycle at G2/M phase and induced cell apoptosis. Mechanistically, compound 13g markedly decreased p-Akt and p-c-Raf expression, which revealed that compound 13g targeted gastric cancer cell lines via interfering with AKT/mTOR and RAS/Raf/MEK/ERK pathways. All the findings suggest that compound 13g might be a valuable lead compound for the anti-gastric cancer agents.
- Jian-Song,Gao, Qiu-Lei,Wu, Bo-Wen,Li, Dong,Shi, Lei,Zhu, Ting,Lou, Jian-Feng,Jin, Cheng-Yun,Zhang, Yan-Bing,Zhang, Sai-Yang,Liu, Hong-Min
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- Wavelength-Dependent Control of the CO Release Kinetics of Manganese(I) Tricarbonyl PhotoCORMs with Benzimidazole Coligands
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A series of photoactivatable CO-releasing molecules (PhotoCORMs) was prepared from manganese pentacarbonyl bromide and 1H-benzimidazol-2-ylmethyl-(N-phenyl)amine ligands (L) bearing different electron-donating and electron-withdrawing groups R = H, 4-CHs
- Mansour, Ahmed M.,Steiger, Christoph,Nagel, Christoph,Schatzschneider, Ulrich
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p. 4572 - 4581
(2019/11/20)
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- Design, synthesis, and biological evaluation of novel benzimidazole derivatives and their interaction with calf thymus DNA and synergistic effects with clinical drugs
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A series of new benzimidazole derivatives was synthesized and characterized by IR, 1H NMR, 13C NMR, MS, and HRMS spectra. All the new compounds were screened for their antimicrobial activities in vitro by a twofold serial dilution technique. The bioactive evaluation showed that 3,5-bis(trifluoromethyl)phenyl benzimidazoles were comparably or even more strongly antibacterial and antifungal than the reference drugs Chloromycin, Norfloxacin, and Fluconazole. The combination of 2,4-difluorobenzyl benzimidazole derivative 5l and its hydrochloride 7 respectively with the antibacterials Chloromycin, Norfloxacin, and the antifungal Fluconazole was more sensitive to methicillin-resistant MRSA and Fluconazole-insensitive A. flavus. In addition, the interaction of compound 5l with calf thymus DNA demonstrated that this compound could effectively intercalate into DNA to form a compound 5l-DNA complex that might block DNA replication and thereby exert good antimicrobial activity.
- Zhang, Huizhen,Lin, Jianmei,Rasheed, Syed,Zhou, Chenghe
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p. 807 - 822
(2014/06/24)
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- A unique one-pot reaction via CC cleavage from aminomethylene benzimidazoles to access benzimidazolones with wide potentiality
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A unique one-pot reaction via CC cleavage from aminomethylene benzimidazoles with commercial halides to access novel benzimidazolones is reported for the first time. The previously unexploited transformation is able to perform smoothly in the presence of
- Zhang, Hui-Zhen,Cui, Sheng-Feng,Nagarajan, Sangaraiah,Rasheed, Syed,Cai, Gui-Xin,Zhou, Cheng-He
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supporting information
p. 4105 - 4109
(2014/07/22)
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- Design, synthesis and antimicrobial evaluation of novel benzimidazole type of Fluconazole analogues and their synergistic effects with Chloromycin, Norfloxacin and Fluconazole
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A novel series of benzimidazole type of Fluconazole analogues were synthesized and characterized by 1H NMR, 13C NMR, IR, MS and HRMS spectra. All the new compounds were screened for their antimicrobial activities in vitro by two-fold serial dilution technique. The bioactive evaluation showed that 3,5-bis(trifluoromethyl)phenyl benzimidazoles gave comparable or even stronger antibacterial and antifungal efficiency in comparison with reference drugs Chloromycin, Norfloxacin and Fluconazole. The combination of 2,4-difluorobenzyl benzimidazole derivative 5m and its hydrochloride 7 respectively with antibacterial Chloromycin, Norfloxacin or antifungal Fluconazole showed better antimicrobial efficiency with less dosage and broader antimicrobial spectrum than the separated use of them alone. Notably, these combined systems were more sensitive to Fluconazole-insensitive Aspergillus flavus and methicillin-resistant MRSA.
- Zhang, Hui-Zhen,Damu, Guri L.V.,Cai, Gui-Xin,Zhou, Cheng-He
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p. 329 - 344
(2013/07/27)
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- Molecular structures of 2-arylaminomethyl-1H-benzimidazole: Spectral, electrochemical, DFT and biological studies
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In the present work, structural studies on (1H-benzimidazol-2-ylmethyl)-N- (4-chloro-phenyl)-amine (L1) and (1H-benzimidazol-2-ylmethyl)-N-(4- iodo-phenyl)-amine (L2) have been done extensively by a variety of physico-chemical techni
- Abdel Ghani, Nour T.,Mansour, Ahmed M.
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experimental part
p. 272 - 284
(2012/05/31)
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- Synthesis of aniline substituted benzimidazole derivatives
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2-Chloromethyl benzimidazole can be synthesized by the reaction of o-phenylene diamine with chloroacetic acid. This on reaction with substituted anilines in presence of ethanolic KOH gives corresponding benzimidazole derivatives. The synthesized compounds were characterized by IR, 1H NMR and mass spectral data.
- Tiwari, Abhishek,Singh, Anita,Tiwari, Varsha
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experimental part
p. 2823 - 2824
(2012/01/19)
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