Antibacterial activities of sulfonyl or sulfonamide containing heterocyclic derivatives and its structure-activity relationships (SAR) studies: A critical review

Verma, Santosh Kumar; Verma, Rameshwari; Xue, Fan; Thakur, Pankaj; Girish, Yarabahally R.; Rakesh, K.P.

doi:10.1016/j.bioorg.2020.104400

Cited by 80 publications

(31 citation statements)

References 97 publications

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“…In contrast, compound 19 has a methoxy group at the para position on the phenethylamine ring. In view of the literature search, the presence of the methoxy group has been effected the antibacterial activity [27] . Ahmed and coworkers also reported that having methoxy groups on the phenyl ring showed excellent antibacterial activity [35] .…”

Section: Resultsmentioning

confidence: 99%

“…In addition, in recent years, structure‐activity relationship studies have shown that the presence and positions of electron‐withdrawing and electron‐donating groups attached to the aromatic ring greatly affect the antibacterial and anticancer properties of the compounds [22–25] . Also, structural modifications can enhance both antimicrobial and anticarcinogenic properties through phenyl ring‐ linked methoxy groups [26,27] …”

Section: Introductionmentioning

confidence: 99%

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Substituted Tetrahydronaphthalen‐1‐yl‐phenethyl Ureas: Synthesis, Characterization, and Biological Evaluations

2022

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Multi‐target drug discovery is one of the most important objectives in the treatment of carcinogenesis because of the different outcomes of the disease such as bacterial infections due to impaired immune systems. Therefore, a series of new urea derivatives were synthesized to acquire both anti‐proliferative and antimicrobial properties that can be used in chemotherapy. The anti‐cancer and anti‐microbial properties of synthesized urea compounds were investigated on the HeLa cancer line and multiple bacterial strains via using WST‐8 and disc diffusion methods. In anticancer investigations against the HeLa cell line, one synthesized urea derivative exhibited the best activity (IC50: 58.9 μM), which showed up to 8 times less toxic effect (SI: 8.5) against the non‐cancerous human dermal fibroblast (PCS201‐012) cell line. Additionally, some urea derivatives showed antibacterial activities against Acinetobacter baumannii, Escherichia coli, Enterococcus faecalis, and Staphylococcus aureus MRSA with the lowest MIC values. The MIC value obtained against Pseudomonas aeruginosa was at the level of μM for all urea derivatives and was calculated as 7.8125 μM. As a result, some synthesized urea derivatives may be considered as multipotent drug formulations with antibacterial and anticancer properties.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Substituted Tetrahydronaphthalen‐1‐yl‐phenethyl Ureas: Synthesis, Characterization, and Biological Evaluations

2022

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“…Amide linkage has been reported in many clinical drugs for metabolic disorders, inflammatory diseases, hypertension, and cancer . Some of the amides containing derivatives have demonstrated excellent BBB permeability and so reported to treat AD. , The sulfonyl functional groups have been important motifs in medicinal chemistry due to its multipurpose favorable pharmacological activities. , In synthetic chemistry, sulfonyl group containing derivatives have been traditionally implicated for the treatment of bacterial infections; however, its beneficial effects are now extended to other pathological conditions such as Alzheimer’s disease, while para-substituted and meta-substituted derivatives offer less steric hindrance and more synthetic yield as compared to ortho-substituted counterpart . Anti-acetylcholine esterases (anti-AchE) are the established anti-AD drugs currently in clinical practice for moderate AD treatment by increasing cholinergic neurotransmission associated with improved cognitive functions .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Benzimidazole Derivatives as Potential Neuroprotective Agents in an Ethanol-Induced Rodent Model

Imran

Shah

Nadeem

et al. 2021

ACS Chem. Neurosci.

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Alzheimer's disease (AD) is the most devastating and progressive neurodegenerative disease in middle to elder aged people, which can be exacerbated by lifestyle factors. Recent longitudinal studies demonstrated that alcohol consumption exacerbates memory impairments in adults. However, the underlying mechanism of alcohol-induced memory impairment is still elusive. The increased cellular manifestation of reactive oxygen species (ROS) and the production of numerous proinflammatory markers play a critical role in the neurodegeneration and pathogenesis of AD. Therefore, reducing neurodegeneration by decreasing oxidative stress and neuroinflammation may provide a potential therapeutic roadmap for the treatment of AD. In this study, eight new benzimidazole acetamide derivatives (FP1, FP2, FP5−FP10) were synthesized and characterized to investigate its neuroprotective effects in ethanol-induced neurodegeneration in a rat model. Further, three derivatives (FP1, FP7, and FP8) were selected for in vivo molecular analysis based on preliminary in vitro antioxidant screening assay. Molecular docking analysis was performed to assess the affinity of synthesized benzimidazole acetamide derivatives against selected proinflammatory targets (TNF-α, IL-6). Biochemical analysis revealed elevated expression of neuroinflammatory markers (TNF-α, NF-κB, IL-6, NLRP3), increased cellular oxidative stress, and reduced antioxidant enzymes in ethanol-exposed rats brain. Notably, pretreatment with new benzimidazole acetamide derivatives (FP1, FP7, and FP8) significantly modulated the ethanol-induced memory deficits, oxidative stress, and proinflammatory markers (TNF-α, NF-κB, IL-6, NLRP3) in the cortex. The multipurpose nature of acetamide containing benzimidazole nucleus and its versatile affinity toward numerous receptors highlight its multistep targeting potential. These results indicated the neuroprotective potential of benzimidazole acetamide derivatives (FP1, FP7, and FP8) as novel therapeutic candidates in ethanol-induced neurodegeneration which may partially be due to inhibition of the neuroinflammatory−oxidative stress vicious cycle.

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“…Nowadays, sulfathiazole bearing heterocyclic moieties have been synthesized and explored for their biological activities with specific target of diseases. Sulfathiazole bearing five member heterocyclic compounds have been widely studied due to their interesting applications as bioactive molecules [ 12 ]. After literature review of these traditional sulfonamides, we are reporting here synthesis of modified new derivatives to achieve sustainability in this area.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, DFT Analysis, and Evaluation of Antibacterial and Antioxidant Activities of Sulfathiazole Derivatives Combined with In Silico Molecular Docking and ADMET Predictions

Samuel

Garg

Mulugeta

2021

Biochemistry Research International

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Synthetic modifications of sulfathiazole derivatives become an interesting approach to enhance their biological properties in line with their applications. As a result, sulfathiazole derivatives become a good candidate and potential class of organic compounds to play an important role towards medicinal chemistry. In present study, one thiazole derivative and two new sulfathiazole derivatives are synthesized with 94% and 72–81% yields, respectively. Furthermore, the synthesized compounds were evaluated for their in vitro antibacterial activity against two Gram-negative (E. coli and P. aeruginosa) and two Gram-positive bacterial strains (S. pyogenes and S. aureus) by disk diffusion method. Among synthesized compounds, compound 11a showed potent inhibitory activity against Gram-negative, E. coli with 11.6 ± 0.283 mm zone of inhibition compared to standard drug sulfamethoxazole (15.7 ± 0.707 mm) at 50 mg/mL. The radical scavenging activities of these compounds were evaluated using DPPH radical assay, and compound 11a showed the strongest activity with IC50 values of 1.655 μg/mL. The synthesized compounds were evaluated for their in silico molecular docking analysis using S. aureus gyrase (PDB ID: 2XCT) and human myeloperoxidase (PDB ID: 1DNU) and were found to have minimum binding energy ranging from −7.8 to −10.0 kcal/mol with 2XCT and −7.5 to −9.7 with 1DNU. Compound 11a showed very good binding score −9.7 kcal/mol with both of the proteins and had promising alignment with in vitro results. Compound 11b also showed high binding scores with both proteins. Drug likeness and ADMET of synthesized compounds were predicted. The DFT analysis of synthesized compounds was performed using Gaussian 09 and visualized through Gauss view 6.0. The structural coordinates of the lead compounds were optimized using B3LYP/6–31 G (d,p) level basis set without any symmetrical constraints. Studies revealed that all the synthesized compounds might be candidates for further antibacterial and antioxidant studies.

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Antibacterial activities of sulfonyl or sulfonamide containing heterocyclic derivatives and its structure-activity relationships (SAR) studies: A critical review

Cited by 80 publications

References 97 publications

Substituted Tetrahydronaphthalen‐1‐yl‐phenethyl Ureas: Synthesis, Characterization, and Biological Evaluations

Substituted Tetrahydronaphthalen‐1‐yl‐phenethyl Ureas: Synthesis, Characterization, and Biological Evaluations

Synthesis and Biological Evaluation of Benzimidazole Derivatives as Potential Neuroprotective Agents in an Ethanol-Induced Rodent Model

Synthesis, DFT Analysis, and Evaluation of Antibacterial and Antioxidant Activities of Sulfathiazole Derivatives Combined with In Silico Molecular Docking and ADMET Predictions

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