Synthesis,<i>in vitro</i>and<i>in vivo</i>antitumor and antiviral activity of novel 1-substituted benzimidazole derivatives

Shaker, Yasser M.; Omar, Mohamed A.; Mahmoud, Khaled; El‐Hallouty, Salwa M.; El‐Senousy, Waled M.; Ali, Mamdouh M.; Mahmoud, Abeer E.; Abdel-Halim, Abeer H.; Soliman, Saeed M.; Diwani, Hoda I. El

doi:10.3109/14756366.2014.979344

Cited by 47 publications

(37 citation statements)

References 40 publications

(40 reference statements)

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“…We initially attempted the reactiono f2 -chloro-1H-benzo[d]imidazole with the in situ generated nitrile oxide,w hichw as pre-pared by the base-mediated dehydrochlorination of N-hydroximoyl chloride 1a.T he reactionw as carried out in the presence of organic and inorganic bases and in aprotic and protic solvents, such as EtOH, MeOH,t etrahydrofuran (THF), dichloromethane (DCM), N,N-dimethylformamide (DMF), isopropanol, 1,4-dioxane, and dimethylsulfoxide (DMSO,T able 1, entries [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18]. At race amounto ft he desired compound 3a (Table 1, entries 3, 4, 10, and 11)w as formed by employing tetra-n-butylammonium fluoride (TBAF)o r4 -(N,N-dimethylamino)pyridine (DMAP)a sb ases (detected by high resolution HPLC-MS and 1 HNMR analysis).…”

Section: Resultsmentioning

confidence: 99%

“…Benzimidazoles and imidazoles are important molecular frameworks that are found in alkaloids, and compounds that contain these structuresg enerally have important biological activity, [1][2][3] including antitumor, [4][5][6] antimicrobial, [7,8] anti-inflammatory, [9,10] and antiviral properties. [11,12] Many commercial drugs also contain this moleculars keleton, such as protonp ump-inhibitors (e.g.,o meprazole) [13,14] and antihelmintics (e.g.,a lbendazole).…”

Section: Introductionmentioning

confidence: 99%

“…Reports of five-membered heteroaromatic-fusedi midazole synthetic methods are rare. We used either 2-chloro-1H-benzo[d]imidazole or 2-chloro-4nitro-1H-imidazole and N-hydroxybenzimidoyl chloride as substrates under moderate conditions to preparee ither 3-phenylbenzo [4,5] [1,2,4]oxadiazole derivatives in high yields. This methodp rovides an approach to obtain heterocyclic compounds that have excellent bioactivity but also contributes towards developments in medicinal chemistry.…”

Section: Introductionmentioning

confidence: 99%

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1,3‐Dipolar Cycloaddition of Imidazole Derivatives with Nitrile Oxide: Synthesis of Imidazo[1,2,4]oxadiazole Derivatives

2017

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Ac oncise and efficient synthesis of imidazo [1,2,4]oxadiazole derivativest hat proceeds through the [3+ +2] cycloaddition of 2-chloro-1H-benzo[d]imidazole with nitrile oxides has been developed. This strategy can conveniently construct tricyclic imidazole heterocyclic derivatives that contain ab road range of functional groups. Compound 3p showede xcellent cytotoxic activity against the KYSE410 cell line (IC 50 = 0.26 mm). These tricyclicimidazole heterocyclic derivatives are promising candidates fordrug discovery.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under https://doi.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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1,3‐Dipolar Cycloaddition of Imidazole Derivatives with Nitrile Oxide: Synthesis of Imidazo[1,2,4]oxadiazole Derivatives

2017

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“…Omeprazole 3 and Pimobendan 4 that are therapeutically useful in the management of peptic ulcer and congestive heart failure, respectively. Many derivatives of benzimidazoles are well known for their antimicrobial, [5][6][7][8][9][10] anthelmintic, 11 antiviral, [12][13][14][15][16] and antifungal 17,18 activities. Since 1985 benzimidazole containing compounds have been reported as well known anticancer agents.…”

Section: Introductionmentioning

confidence: 99%

New approaches for the synthesis, cytotoxicity and toxicity of heterocyclic compounds derived from 2-cyanomethyl benzo[c]imidazole

Mohareb

Mohamed²,

Abdallah³

2016

ACSi

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The reaction of ethyl cyanoacetate with o-phenylenediamine gave the 2-cyanomethylbenzo[c]imidazole (1). The latter compound was used as the key starting material to synthesise biologically active heterocyclic derivatives. Thus, the reaction of 1 with cyclohexanone and either of benzaldehyde, 4-methoxybenzaldehyde or 4-chlorobenzaldehyde gave the annulated derivatives 2a-c, respectively. The antitumor evaluations of the newly synthesized products against the three cancer cell lines MCF-7 (breast adeno-carcinoma), NCI-H460 (non-small cell lung cancer) and SF-268 (CNS cancer) showed that compounds 2b, 6, 11b, 11c, 12b, 16a, 16b and 18a exhibited optimal cytotoxic effect against cancer cell lines, with IC 50 values in the nM range. Bioactive compounds are often toxic to shrimp larvae. Thus, in order to monitor these chemicals in vivo lethality to shrimp larvae (Artemia salina), Brine-Shrimp Lethality Assay was used. Compounds 11b, 12b and 16b showed no toxicity against the tested organisms.

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“…It acts by blocking cell growth or by inhibiting the enzymes responsible in the nucleic acid formation process. This inhibition prevents DNA transcription, which causes cell death [10][11][12][13]. Many studies have revealed the importance of benzimidazoles as anticancer agents including bendamustine, dovitinib, Hoechst 33342, and Hoechst 33258 (Fig.…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative, Cytotoxic, and Apoptotic Effects of New Benzimidazole Derivatives Bearing Hydrazone Moiety

Çevik

Sağlık

Korkut

et al. 2017

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).In order to take the advantages of the anticancer properties of benzimidazoles and hydrazones, we synthesized new 4-(5-chloro-1H-benzimidazol-2-yl)-benzoic acid benzylidene hydrazide derivatives (3a-3t) and evaluated their anticancer activity against A549 (human lung adenocarcinoma) and MCF-7 (human breast adenocarcinoma) cells. The structures of the compounds (3a-3t) were confirmed by IR, 1 H-NMR, 13 C-NMR, mass spectroscopy, and elemental analyses. Antiproliferative activities of the compounds were evaluated using MTT assay, BrdU method, and flow cytometric analysis. In addition, with purpose of determining selectivity the cytotoxic activities of the final compounds were screened against healthy NIH3T3 cell line (mouse vembryonic fibroblast cells). Among the tested compounds 3e and 3f showed significant cytotoxic activity against A549 and MCF-7 cancer cells with an IC 50 value of 0.0316 μM. Furthermore, compound 3p showed remarkable cytotoxic activity against MCF-7 comparing with standard drug cisplatin. Annexin V-FITC assay also suggested that this compounds induced cell death by apoptosis.

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Synthesis,in vitroandin vivoantitumor and antiviral activity of novel 1-substituted benzimidazole derivatives

Cited by 47 publications

References 40 publications

1,3‐Dipolar Cycloaddition of Imidazole Derivatives with Nitrile Oxide: Synthesis of Imidazo[1,2,4]oxadiazole Derivatives

1,3‐Dipolar Cycloaddition of Imidazole Derivatives with Nitrile Oxide: Synthesis of Imidazo[1,2,4]oxadiazole Derivatives

New approaches for the synthesis, cytotoxicity and toxicity of heterocyclic compounds derived from 2-cyanomethyl benzo[c]imidazole

Antiproliferative, Cytotoxic, and Apoptotic Effects of New Benzimidazole Derivatives Bearing Hydrazone Moiety

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