Synthesis and Structure Activity Relationship of Some Indole Derivatives as Potential Anti-inflammatory Agents

Fatahala, Samar S.; Khedr, Mohammed A.; Mohamed, Mossad S.

doi:10.17344/acsi.2017.3481

Cited by 14 publications

(10 citation statements)

References 69 publications

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“…Indoles have been identified as a privileged scaffold for the design of medicinal drugs (O'Connor and Maresh, 2006;Liu et al, 2009;Biersack and Schobert, 2012), 3-selenylindoles are a significant class of indole compounds as they are bioactive (Nogueira et al, 2004), and the amido group is a very important substituent in medicinal chemistry. Amide-containing compounds are widely present in natural products and pharmaceuticals, displaying a wide range of biological activities, such as anticancer and antiviral properties (Fatahala et al, 2017). Considering the dominance of 3-selenylindole and the amido group in nature and their impact in medicinal chemistry, we designed a novel compound SYG-180-2-2 containing these two frameworks.…”

Section: Introductionmentioning

confidence: 99%

Small-Molecule Compound SYG-180-2-2 to Effectively Prevent the Biofilm Formation of Methicillin-Resistant Staphylococcus aureus

et al. 2022

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The resistance of methicillin-resistant Staphylococcus aureus (MRSA) has augmented due to the abuse of antibiotics, bringing about difficulties in the treatment of infection especially with the formation of biofilm. Thus, it is essential to develop antimicrobials. Here we synthesized a novel small-molecule compound, which we termed SYG-180-2-2 (C21H16N2OSe), that had antibiofilm activity. The aim of this study was to demonstrate the antibiofilm effect of SYG-180-2-2 against clinical MRSA isolates at a subinhibitory concentration (4 μg/ml). In this study, it was showed that significant suppression in biofilm formation occurred with SYG-180-2-2 treatment, the inhibition ranged between 65.0 and 85.2%. Subsequently, confocal laser scanning microscopy and a bacterial biofilm metabolism activity assay further demonstrated that SYG-180-2-2 could suppress biofilm. Additionally, SYG-180-2-2 reduced bacterial adhesion and polysaccharide intercellular adhesin (PIA) production. It was found that the expression of icaA and other biofilm-related genes were downregulated as evaluated by RT-qPCR. At the same time, icaR and codY were upregulated when biofilms were treated with SYG-180-2-2. Based on the above results, we speculate that SYG-180-2-2 inhibits the formation of biofilm by affecting cell adhesion and the expression of genes related to PIA production. Above all, SYG-180-2-2 had no toxic effects on human normal alveolar epithelial cells BEAS-2B. Collectively, the small-molecule compound SYG-180-2-2 is a safe and effective antibacterial agent for inhibiting MRSA biofilm.

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Section: Introductionmentioning

confidence: 99%

Small-Molecule Compound SYG-180-2-2 to Effectively Prevent the Biofilm Formation of Methicillin-Resistant Staphylococcus aureus

et al. 2022

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“…Pyrroles and its fused derivatives, are an important class of naturally 22,23 and synthetically [24][25][26] occurring compounds with a wide-range of biological activities; antibacterial [27][28][29] , antifungal [30][31][32][33] , antiviral [34][35][36][37][38][39] , anticancer 40,41 and anti-inflammatory 42,43 . Pyrrolnitin and fludioxonil, are two naturally secreted pyrroles, reported to bear a broad spectrum antifungal activities [44][45][46] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel pyrroles and fused pyrroles as antifungal and antibacterial agents

El-Hameed

Sayed

Ali

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Pyrroles and its fused forms possess antimicrobial activities, they can easily interact with biomolecules of living systems. A series of substituted pyrroles, and its fused pyrimidines and triazines forms have been synthesised, all newly synthesised compound structures were confirmed by spectroscopic analysis. Generally, the compounds inhibited growth of some important human pathogens, the best effect was given by: 2a, 3c, 4d on Gram-positive bacteria and was higher on yeast ( C. albican s), by 5c on Gram-negative bacteria and by 5a then 3c on filamentous fungi (A. fumigatus and F. oxysporum ). Such results present good antibacterial and antifungal potential candidates to help overcome the global problem of antibiotic resistance and opportunistic infections outbreak. Compound 3c gave the best anti-phytopathogenic effect at a 50-fold lower concentration than Kocide 2000, introducing a safe commercial candidate for agricultural use. The effect of the compounds on DNA was monitored to detect the mode of action.

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“…Indole, an aromatic heterocyclic organic compound, has attracted the interest of scientists since it possesses a wide variety of pharmacological properties, such as analgesic [3,4], anti-inflammatory [3,5,6], antimicrobial [7][8][9][10], anticancer [11][12][13], anticonvulsant [14,15] and antiviral [16,17], COX-inhibitory [18,19], antidiabetic [20,21], and antitubercular [22,23] activities. Furthermore, indole moiety is present in some drug molecules, such as: indomethacin; yohimbine, an approved drug for the treatment of sexual disorders [24,25]; delavirdine, anti-HIV drug [26]; reserpine (Figure 1), and many others.…”

Section: Introductionmentioning

confidence: 99%

4-(Indol-3-yl)thiazole-2-amines and 4-ιndol-3-yl)thiazole Acylamines as Νovel Antimicrobial Agents: Synthesis, In Silico and In Vitro Evaluation

Simakov

Карцев²,

Petrou

et al. 2021

Pharmaceuticals

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This manuscript deals with the synthesis and computational and experimental evaluation of the antimicrobial activity of twenty-nine 4-(indol-3-yl)thiazole-2-amines and 4-ιndol-3-yl)thiazole acylamines. An evaluation of antibacterial activity against Gram (+) and Gram (−) bacteria revealed that the MIC of indole derivatives is in the range of 0.06–1.88 mg/mL, while among fourteen methylindole derivatives, only six were active, with an MIC in the range of of 0.47–1.88 mg/mL. S. aureus appeared to be the most resistant strain, while S. Typhimurium was the most sensitive. Compound 5x was the most promising, with an MIC in the range of 0.06–0.12 mg/mL, followed by 5d and 5m. An evaluation of these three compounds against resistant strains, namely MRSA P. aeruginosa and E. coli, revealed that they were more potent against MRSA than ampicillin. Furthermore, compounds 5m and 5x were superior inhibitors of biofilm formation, compared to ampicillin and streptomycin, in terms Compounds 5d, 5m, and 5x interact with streptomycin in additive manner. The antifungal activity of some compounds exceeded or was equipotent to those of the reference antifungal agents bifonazole and ketoconazole. The most potent antifungal agent was found to be compound 5g. Drug likeness scores of compounds was in a range of −0.63 to 0.29, which is moderate to good. According to docking studies, E. coli MurB inhibition is probably responsible for the antibacterial activity of compounds, whereas CYP51 inhibition was implicated in antifungal activity. Compounds appeared to be non-toxic, according to the cytotoxicity assessment in MRC-5 cells.

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Synthesis and Structure Activity Relationship of Some Indole Derivatives as Potential Anti-inflammatory Agents

Cited by 14 publications

References 69 publications

Small-Molecule Compound SYG-180-2-2 to Effectively Prevent the Biofilm Formation of Methicillin-Resistant Staphylococcus aureus

Small-Molecule Compound SYG-180-2-2 to Effectively Prevent the Biofilm Formation of Methicillin-Resistant Staphylococcus aureus

Synthesis of novel pyrroles and fused pyrroles as antifungal and antibacterial agents

4-(Indol-3-yl)thiazole-2-amines and 4-ιndol-3-yl)thiazole Acylamines as Νovel Antimicrobial Agents: Synthesis, In Silico and In Vitro Evaluation

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