Anticancer, antimicrobial and antioxidant potential of sterically tuned bis-<i>N</i>-heterocyclic salts

Huda, Noor ul; Islam, Saiful; Zia, Muhammad; William, Kainaat; Abbas, Fakhar I; Umar, Muhammad Ihtisham; Iqbal, Muhammad Adnan; Mannan, Abdul

doi:10.1515/znc-2018-0095

Cited by 8 publications

(3 citation statements)

References 51 publications

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“…In a previous study, 1,2-disubstituted 1 H -benzimidazole derivatives with n -propyl and n -hexyl groups displayed their potency to inhibit MRSA (N315), with MIC values ranging from 4 1 to 8 μg mL ‑1 . , Noor ul Huda and co-workers synthesized six 3,3′-(1,3-phenylene (methylene)(1-alkyl-benzimidazolium) salts with a long chain at the N-1 position (butyl, propyl, benzyl, isopropyl, ethyl, and heptyl) and screened them for their antibacterial efficacy. Among the six derivatives, the compound bearing the heptyl group displayed the best zone of inhibition (21.00 mm against S. aureus and 21.60 mm against MRSA10 and MRSA11) due to its longest straight chain, which facilitated enhanced absorption into the cells.…”

Section: Resultsmentioning

confidence: 99%

Exploration of Remarkably Potential Multitarget-Directed N-Alkylated-2-(substituted phenyl)-1H-benzimidazole Derivatives as Antiproliferative, Antifungal, and Antibacterial Agents

et al. 2023

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Improving lipophilicity for drugs to penetrate the lipid membrane and decreasing bacterial and fungal coinfections for patients with cancer pose challenges in the drug development process. Here, a series of new N-alkylated-2-(substituted phenyl)-1H-benzimidazole derivatives were synthesized and characterized by 1 H and 13 C NMR, FTIR, and HRMS spectrum analyses to address these difficulties. All the compounds were evaluated for their antiproliferative, antibacterial, and antifungal activities. Results indicated that compound 2g exhibited the best antiproliferative activity against the MDA-MB-231 cell line and also displayed significant inhibition at minimal inhibitory concentration (MIC) values of 8, 4, and 4 μg mL −1 against Streptococcus faecalis, Staphylococcus aureus, and methicillin-resistant Staphylococcus aureus compared with amikacin. The antifungal data of compounds 1b, 1c, 2e, and 2g revealed their moderate activities toward Candida albicans and Aspergillus niger, with MIC values of 64 μg mL −1 for both strains. Finally, the molecular docking study found that 2g interacted with crucial amino acids in the binding site of complex dihydrofolate reductase with nicotinamide adenine dinucleotide phosphate.

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Section: Resultsmentioning

confidence: 99%

Exploration of Remarkably Potential Multitarget-Directed N-Alkylated-2-(substituted phenyl)-1H-benzimidazole Derivatives as Antiproliferative, Antifungal, and Antibacterial Agents

et al. 2023

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“…Compound 28 exhibited prominent activity against HCT-116 cancer cell lines showing 75% inhibition at 1 mg/ml as determined by using sulforhodamine Β assay. Compound 28 contains a lipophilic alkyl chain and the lipophilicity of the alkyl chain was linked to the increased activity of this derivative [48].…”

Section: Benzimidazolium Salts Having Aromatic and Aliphatic Substitu...mentioning

confidence: 99%

The Anticancer Profile of Benzimidazolium Salts and Their Metal Complexes

Khan¹,

Mohsin²,

Aslam³

et al. 2022

Benzimidazole

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Cancer is the most lethal ailment throughout the world in the present era. The development of new anticancer remedies with minor unhealthful effects and an alternate mechanism is crucial. Benzimidazole is a distinguished heterocyclic compound and is now recognized as the privileged scaffold for new drug discovery. This chapter deals with the anticancer capability of benzimidazolium salts and their metal complexes. The benzimidazolium derivatives have been prepared by the introduction of aliphatic and aromatic groups at two nitrogen atoms of the benzimidazole ring. Other modifications include hybridization with other pharmacophores and the preparation of metal complexes. The potent derivatives presented in this review can serve as novel drug candidates against cancer.

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“…Huda et al [159] designed and synthesized novel hybrids of 1,1′‐(1,3‐phenylene bis(methylene))bis(3‐alkyl/aryl‐1 H ‐benzimidazol‐3‐ium) salts and examined their anticancer activity against HCT‐116 (CRC) and MCF‐7 (human breast cancer cell lines) by SRB assay. Out of all, compound 127 (IC 50 = 14.63 μg/ml).…”

Section: Benzimidazole As Target Oriented Anticancer Agentsmentioning

confidence: 99%

Benzimidazole based derivatives as anticancer agents: Structure activity relationship analysis for various targets

Satija

Sharma

Madan

et al. 2021

Journal of Heterocyclic Chem

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Benzimidazole, the benzo derivative of imidazole, is a class of bicyclic aromatic organic compound consisting of six‐membered benzene ring fused to five‐membered imidazole at 4‐ and 5‐positions of the imidazole ring. It is a vital pharmacophore of many biologically active heterocyclic compounds with a variety of pharmacological activities. Over the time, benzimidazole and its derivatives have evolved as vibrant heterocyclic systems due to their potency in a wide range of bioactive compounds like analgesics, antifungals, anti‐inflammatory, antihypertensives, proton pump inhibitors, anti‐HIV, antiviral, and so on. Multi‐drug resistance in cancer that led to the failure of many chemotherapeutic drugs is a major concern. Various approaches are being developed to overcome this problem. One of them is target based drug discovery, which is an effective method to develop a novel anticancer drug. To develop newer drugs, previously reported work needs to be studied. Keeping this in mind, last 5 years literature on benzimidazole used as anticancer agents has been reviewed and summarized in the paper herein. This review article along with the target of cancer also deal with structure activity relationship of various compounds having benzimidazole ring.

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Anticancer, antimicrobial and antioxidant potential of sterically tuned bis-N-heterocyclic salts

Cited by 8 publications

References 51 publications

Exploration of Remarkably Potential Multitarget-Directed N-Alkylated-2-(substituted phenyl)-1H-benzimidazole Derivatives as Antiproliferative, Antifungal, and Antibacterial Agents

Exploration of Remarkably Potential Multitarget-Directed N-Alkylated-2-(substituted phenyl)-1H-benzimidazole Derivatives as Antiproliferative, Antifungal, and Antibacterial Agents

The Anticancer Profile of Benzimidazolium Salts and Their Metal Complexes

Benzimidazole based derivatives as anticancer agents: Structure activity relationship analysis for various targets

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