Design, synthesis and biological evaluation of 2-substituted-6-[(4-substituted-1-piperidyl)methyl]-1H-benzimidazoles as inhibitors of ebola virus infection

Bessières, Maxime; Plebanek, Elżbieta; Chatterjee, Payel; Shrivastava-Ranjan, Punya; Flint, Mike; Spiropoulou, Christina F.; Warszycki, Dawid; Bojarski, Andrzej J.; Roy, Vincent; Agrofoglio, Luigi A.

doi:10.1016/j.ejmech.2021.113211

Cited by 13 publications

(8 citation statements)

References 44 publications

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“…In the first step, α,α’-dibromo or dichloro- I -xylene ( I = o , m , p ) undergoes the Arbuzov reaction with triethyl phosphite to give diethyl (halogenomethyl)benzylphosphonates 6a – c following the procedure developed by Bessieres et al [ 35 ]. Compounds 6a – c were obtained in high yields (71–84%) and were consecutively characterized by spectroscopic methods ( 1 H, 13 C NMR, IR) and mass spectrometry.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Studies of Novel Aminophosphonates and Their Metal Carbonyl Complexes (Fe, Ru)

Kosińska

Virieux

Pirat

et al. 2022

IJMS

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The quest to find new inhibitors of biologically relevant targets is considered an important strategy to introduce new drug candidates for the treatment of neurodegenerative diseases. A series of (aminomethyl)benzylphosphonates 8a–c and their metallocarbonyl iron 9a–c and ruthenium 10a–c complexes were designed, synthesized, and evaluated for their inhibitory potentials against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) by determination of IC50. Metallocarbonyl derivatives, in general, did not show significant inhibition activity against these enzymes, the most potent inhibitor was the (aminomethyl)benzylphosphonate 8a (IC50 = 1.215 µM against AChE). Molecular docking analysis of AChE and (aminomethyl)benzylphosphonates 8a–c showed the strongest interactions of 8a and AChE compared to isomers 8b and 8c. Cytotoxicity studies of synthesized compounds towards the V79 cell line were also performed and discussed.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Studies of Novel Aminophosphonates and Their Metal Carbonyl Complexes (Fe, Ru)

Kosińska

Virieux

Pirat

et al. 2022

IJMS

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“…Compound (101) has been synthesized in a multi-step process by Bessieres et al in 2021 (Figure 26) [84]. A study about the inhibition of Ebola virus infection resulted in the design of a more potent and selective drug than the reference drug, Toremifene.…”

Section: Antiviral Activitymentioning

confidence: 99%

Exploring the Versatility of Benzimidazole Scaffolds as Medicinal Agents: A Brief Update

Kavya¹,

Sivan²

2022

Benzimidazole

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Benzimidazole, one of the finest classes of heterocyclic aromatic compounds have the characteristic structure of benzene fused with a five-membered imidazole ring. Despite being made their first appearance in the late 1870s, they are considered as a ‘privileged molecule’. The applications of this wonder molecule range from medicinal chemistry to material science. Benzimidazole being a potent inhibitor for various enzymes has got therapeutic effects like anticancer, antimicrobial, anthelmintic, antioxidant, anticonvulsant, antifungal, anti-inflammatory, antiviral, antihistaminic, antipsychotic, etc. It has also made its existence in various branches of medical science viz ophthalmology, neurology, cardiology and more. The applications of benzimidazole are not only limited to the biological field but also expanded to the field of material chemistry as well. This chapter summarizes the pharmacological properties of benzimidazole, illustrated on numerous derivatives since 2016.

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“…It is well known that benzimidazoles have antibacterial, 1 antimicrobial, [2][3][4][5] and antifungal 6 activities. Furthermore, several benzimidazoles show promising pharmacological activities such as antioxidant, [7][8][9] anticancer, 10 anti-inflammatory, 11 antiprotozoal, 12 antiviral, 13 antidiabetic, 14 antihypertensive, 15 antimycobacterial, 16 and antithrombin, 17 as well as tubulin 18 and dipeptidyl peptidase III 19 inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Novel Benzimidazole-Based Compounds as Antimicrobials: Synthesis, Molecular Docking, Molecular Dynamics and in silico ADME Profile Studies

Yeşilçayır

Çeli̇k²,

Şen³

et al. 2022

ACSi

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Some novel benzimidazole derivatives were synthesized and their antimicrobial activities were evaluated. Compounds 3a and 3b exhibited excellent antibacterial activity with MIC values <4 μg/mL against Staphylococcus aureus ATCC 29213 (MSSA) and Staphylococcus aureus ATCC 43300 (MRSA). Molecular docking analyzes of compounds with MIC values of 16 μg/mL and below against gram-positive bacteria and fungi were performed using FabH (β-ketoacyl-acyl carrier protein synthase III) as bacterial protein and CYP51 (sterol 14α-demethylase) as the fungal target protein. According to the molecular docking analysis, it was calculated that sufficient protein-ligand interaction energy was liberated between the compounds 2f, 3a, 3b, 3e and 3h and the antibacterial target protein FabH and strong interactions were formed between 2f and 3h and the antifungal target protein. According to RMSD, RMSF and MMPBSA measurements obtained from molecular dynamics, it is understood that compounds 3a and 3b maintain protein-ligand stability in silico physiological conditions.

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Design, synthesis and biological evaluation of 2-substituted-6-[(4-substituted-1-piperidyl)methyl]-1H-benzimidazoles as inhibitors of ebola virus infection

Cited by 13 publications

References 44 publications

Synthesis and Biological Studies of Novel Aminophosphonates and Their Metal Carbonyl Complexes (Fe, Ru)

Synthesis and Biological Studies of Novel Aminophosphonates and Their Metal Carbonyl Complexes (Fe, Ru)

Exploring the Versatility of Benzimidazole Scaffolds as Medicinal Agents: A Brief Update

Novel Benzimidazole-Based Compounds as Antimicrobials: Synthesis, Molecular Docking, Molecular Dynamics and in silico ADME Profile Studies

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