Synthesis, antimicrobial and antiviral activity of substituted benzimidazoles

Sharma, Deepika; Narasimhan, Balasubramanian; Kumar, Pradeep; Judge, Vikramjeet; Narang, Rakesh; Clercq, Erik De; Balzarini, Jan

doi:10.1080/14756360802694427

Cited by 63 publications

(37 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, in medicine they are not used for treatment of fungal infections but rather as antihelminthics (mebendazole, eskazole). Many other derivatives have previously been described to have antifungal activities (12,39). In addition, an antineoplastic activity of certain benzimidazoles, like nocodazole, has been identified, pointing to a certain level of cytotoxic effects.…”

Section: Discussionmentioning

confidence: 99%

A Screening Assay Based on Host-Pathogen Interaction Models Identifies a Set of Novel Antifungal Benzimidazole Derivatives

Burger‐Kentischer

Finkelmeier

Keller

et al. 2011

Antimicrob Agents Chemother

View full text Add to dashboard Cite

Fungal infections are a serious health problem in clinics, especially in the immune-compromised patient. Disease ranges from widespread superficial infections like vulvovaginal infections to life-threatening systemic candidiasis. Especially for systemic mycoses, only a limited arsenal of antifungals is available. The most commonly used classes of antifungal compounds used include azoles, polyenes, and echinocandins. Due to emerging resistance to standard therapy, significant side effects, and high costs for several antifungals, there is a medical need for new antifungals in the clinic and general practice. In order to expand the arsenal of compounds with antifungal activities, we screened a compound library including more than 35,000 individual compounds derived from organic synthesis as well as combinatorial compound collections representing mixtures of compounds for antimycotic activity. In total, more than 100,000 compounds were screened using a new type of activity-selectivity assay, analyzing both the antifungal activity and the compatibility with human cells at the same time. One promising hit, an (S)-2-aminoalkyl benzimidazole derivative, was developed among a series of lead compounds showing potent antifungal activity. (S)-2-(1-Aminoisobutyl)-1-(3-chlorobenzyl) benzimidazole showed the highest antifungal activity and the best compatibility with human cells in several cell culture models and against a number of clinical isolates of several species of pathogenic Candida yeasts. Transcriptional profiling indicates that the newly discovered compound is a potential inhibitor of the ergosterol pathway, in contrast to other benzimidazole derivatives, which target microtubules.

show abstract

Section: Discussionmentioning

confidence: 99%

A Screening Assay Based on Host-Pathogen Interaction Models Identifies a Set of Novel Antifungal Benzimidazole Derivatives

Burger‐Kentischer

Finkelmeier

Keller

et al. 2011

Antimicrob Agents Chemother

View full text Add to dashboard Cite

show abstract

“…Gram positive bacteria ( S. aureus and B. subtilis ), Gram negative bacteria ( E. coli, P. aeruginosa and S. enterica ) and fungal strain ( C. albicans and A. niger ) then their minimum bactericidal concentration (MBC) and fungicidal concentration (MFC) were determined by petri dish method using nutrient agar media (antibacterial) and sabouraud dextrose agar media (antifungal) by subculturing 100 μl of culture from each test tube that remained clear in the MIC determination into fresh medium. The MBC and MFC values represent the lowest concentration of compound that produces in the range of 96–98% end point reduction of the used test bacterial and fungal species [19]. …”

Section: Resultsmentioning

confidence: 99%

Design, synthesis and antimicrobial evaluation of pyrimidin-2-ol/thiol/amine analogues

Narwal

Kumar

Verma

2017

Chemistry Central Journal

View full text Add to dashboard Cite

BackgroundPyrimidine is an aromatic heterocyclic moiety containing nitrogen atom at 1st and 3rd positions and play an important role to forms the central core for different necessity of biological active compounds, from this facts, we have designed and synthesized a new class of pyrimidin-2-ol/thiol/amine derivatives and screened for its in vitro antimicrobial activity.Results and discussionThe synthesized pyrimidine derivatives were confirmed by IR, 1H/13C-NMR, Mass spectral studies and evaluated for their in vitro antimicrobial potential against Gram positive (S. aureus and B. subtilis), Gram negative (E. coli, P. aeruginosa and S. enterica) bacterial strains and fungal strain (C. albicans and A. niger) by tube dilution method and recorded minimum inhibitory concentration in µM/ml. The MBC and MFC values represent the lowest concentration of compound that produces in the range of 96–98% end point reduction of the used test bacterial and fungal species.ConclusionIn general all synthesized derivatives exhibited good antimicrobial activity. Among them, compounds 2, 5, 10, 11 and 12 have significant antimicrobial activity against used bacterial and fungal strains and also found to be more active than the standard drugs.Graphical abstractPyrimidine is an aromatic heterocyclic moiety containing nitrogen atom at 1st and 3rd positions and play an important role to forms the central core for different necessity of biological active compounds, from this facts, we have designed and synthesized a new class of pyrimidin-2-ol/thiol/amine derivatives and screened for its in vitro antimicrobial activity. The synthesized pyrimidine derivatives were confirmed by IR, 1H/13C-NMR, Mass spectral studies and evaluated for their in vitro antimicrobial potential against Gram positive (S. aureus and B. subtilis), Gram negative (E. coli, P. aeruginosa and S. enterica) bacterial strains and fungal strain (C. albicans and A. niger) by tube dilution method and recorded minimum inhibitory concentration in µM/ml. The MBC and MFC values represent the lowest concentration of compound that produces in the range of 96–98% end point reduction of the used test bacterial and fungal species.

show abstract

“…A variety of new synthetic molecules capable of anion-recognition have been synthesized that offer hydrogen bonding includes, amides [6][7][8], protonated amine [9], guanidinium [10], indole [11][12][13], pyrroles [14,15], urea/thiourea [16,17] and benzimidazole [18]. Benzimidazole a hetero-aryl compound is an essential pharmacophore in the drug discovery and is associated with a wide range of biological activities [19][20][21][22]. The crystal structures of numerous benzimidazole based ligands, illustrates their potential as excellent hydrogen bond donors for the anions.…”

Section: Introductionmentioning

confidence: 99%