A novel series of N-acyl substituted indole-linked benzimidazoles and naphthoimidazoles as potential anti inflammatory, anti biofilm and anti microbial agents

Rajan, Anbarasan; Prakash, P.; Mahendran, Karthikeyan; Ramanathan, Murugappan

doi:10.1016/j.micpath.2017.12.021

Cited by 31 publications

(9 citation statements)

References 31 publications

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“…Moreover, a number of bioactive clinical candidates (Figure a) for example, Indomethacin, Arbidol and Indibulin were identified to possess N‐substituted indole framework. Various N‐substituted indoles with promising antifungal and anti‐biofilm activities were also reported previously (Figure b) which urged us to incorporate N‐substituted indole framework in the investigation of new antifungal agents.…”

Section: Introductionsupporting

confidence: 54%

Design, Synthesis and Biological Evaluation of Substituted (1‐(4‐chlorobenzyl)‐1H‐indol‐3‐yl) 1H‐(1,2,3‐triazol‐4‐yl)methanones as Antifungal Agents

et al. 2019

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In the perusal of our endeavour towards the synthesis of new bioactive agents, a new series of substituted (1‐(4‐chlorobenzyl)‐1H‐indol‐3‐yl) 1H‐(1,2,3‐triazol‐4‐yl) methanones (8a‐u) were designed, synthesized and investigated for their antimicrobial activity with special emphasis on their anti‐Candida potential and Candida biofilm inhibition. Among them, the hybrids 8e, 8f, and 8o demonstrated significant antifungal activity on most of the tested fungal strains with MIC values ranging between 1.9–7.8 μg/mL. In addition, the most promising compounds were found to be effective biofilm inhibitors. We have studied the Field emission Scanning Electron Microscope (FE‐SEM) micrographs for 8f to know the damage of the cells with altered membrane integrity and release of intracellular contents thereby validating the in vitro biofilm inhibition assay. Further, in enzymatic assay, active compounds inhibited ergosterol biosynthesis. Furthermore, docking studies revealed that they effectively bind to 14α‐demethylase (CYP51), thereby inhibiting ergosterol biosynthesis. Interestingly, they exhibited lower cytotoxicity in the normal cell line (MRC5).

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Section: Introductionsupporting

confidence: 54%

Design, Synthesis and Biological Evaluation of Substituted (1‐(4‐chlorobenzyl)‐1H‐indol‐3‐yl) 1H‐(1,2,3‐triazol‐4‐yl)methanones as Antifungal Agents

et al. 2019

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“…Recently, the antibacterial and anti-inflammatory activities of naphthoimidazoles were published. (26) For protozoa, all previous reports were authored by our group. Mechanistic studies revealed the activity of these naphthoquinone derivatives against all T. cruzi stages in vitro and revealed the mitochondrion as the main target.…”

Section: Discussionmentioning

confidence: 99%

Antiparasitic and anti-inflammatory activities of ß-lapachone-derived naphthoimidazoles in experimental acute Trypanosoma cruzi infection

Cascabulho

Meuser-Batista

Moura

et al. 2020

Mem. Inst. Oswaldo Cruz

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BACKGROUND Chagas disease, which is caused by the protozoan Trypanosoma cruzi, is endemic to Latin America and mainly affects low-income populations. Chemotherapy is based on two nitrocompounds, but their reduced efficacy encourages the continuous search for alternative drugs. Our group has characterised the trypanocidal effect of naphthoquinones and their derivatives, with naphthoimidazoles derived from β-lapachone (N1, N2 and N3) being the most active in vitro. OBJECTIVES In the present work, the effects of N1, N2 and N3 on acutely infected mice were investigated. METHODS in vivo activity of the compounds was assessed by parasitological, biochemical, histopathological, immunophenotypical, electrocardiographic (ECG) and behavioral analyses. FINDINGS Naphthoimidazoles led to a decrease in parasitaemia (8 dpi) by reducing the number of bloodstream trypomastigotes by 25-50% but not by reducing mortality. N1 protected mice from heart injury (15 dpi) by decreasing inflammation. Bradycardia was also partially reversed after treatment with N1 and N2. Furthermore, the three compounds did not reverse hepatic and renal lesions or promote the improvement of other evaluated parameters. MAIN CONCLUSION N1 showed moderate trypanocidal and promising immunomodulatory activities, and its use in combination with benznidazole and/or anti-arrhythmic drugs as well as the efficacy of its alternative formulations must be investigated in the near future.

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“…Benzimidazoles moieties linked with N-acyl substituted indole (81-86) were demonstrated by Abraham et al [75]. The assessment of antimicrobial activity was done against gram-negative and gram-positive bacteria like Pseudomonas aeruginosa (MTCC424), Staphylococcus aureus (MTCC 2940), Escherichia coli (MTCC 443), and Enterococcus fecalis.…”

Section: Antibacterial and Antifungal 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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A novel series of N-acyl substituted indole-linked benzimidazoles and naphthoimidazoles as potential anti inflammatory, anti biofilm and anti microbial agents

Cited by 31 publications

References 31 publications

Design, Synthesis and Biological Evaluation of Substituted (1‐(4‐chlorobenzyl)‐1H‐indol‐3‐yl) 1H‐(1,2,3‐triazol‐4‐yl)methanones as Antifungal Agents

Design, Synthesis and Biological Evaluation of Substituted (1‐(4‐chlorobenzyl)‐1H‐indol‐3‐yl) 1H‐(1,2,3‐triazol‐4‐yl)methanones as Antifungal Agents

Antiparasitic and anti-inflammatory activities of ß-lapachone-derived naphthoimidazoles in experimental acute Trypanosoma cruzi infection

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

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