Design, synthesis, molecular docking, antimicrobial, and antioxidant activities of new phenylsulfamoyl carboxylic acids of pharmacological interest

Egbujor, Melford C.; Okoro, Uchechukwu C.; Okafor, Sunday N.

doi:10.1007/s00044-019-02440-3

Cited by 14 publications

(11 citation statements)

References 12 publications

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“…For the antibacterial, compound 3 had a better binding affinity (-10.95 kcal/mol) than penicillin (-10.89 kcal/mol) while antifungal study revealed that compounds 3 and 4 had binding affinities (-10.07 and -10.62 kcal/mol, respectively) comparable to ketoconazole (-10.85 kcal/mol). The high binding affinity of compound 3 is due to the fact that sulphamoyl carboxylic acids have excellent in silico antibacterial activities ( 41 ). It implies that compounds 3 and 4 had the best in silico antimicrobial activities.…”

Section: Discussionmentioning

confidence: 99%

Design, synthesis, and molecular docking of cysteine-based sulphonamide derivatives as antimicrobial agents

et al. 2022

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Background and purpose: The preponderance of microbial infections remains a global challenge. In the present study, synthesis of novel cysteine-based antimicrobial agents and their biological evaluation is reported. Experimental approach: The reaction of p -toluenesulphonyl chloride with cysteine afforded 2-{[(4-methylphenyl)sulphonyl]amino}-3-sulphanylpropanoic acid (3) which was acetylated based on Lumiere-Barbier method using acetic anhydride. The ammonolysis of the acetylated compound (4) gave the carboxamide derivative ( 5 ) which reacted with aniline, aminopyridine and diaminopyrimidine via nickel catalyzed Buchwald-Hartwig amidation reaction to afford compounds 6a, 6b, and 6c , respectively. The compounds were characterized using FTIR, 1 H-NMR, 13 C-NMR, and elemental analysis. The in vitro antimicrobial activities were determined. Their physicochemical properties were generated in silico and the molecular docking studied bacterial and fungal infections. Findings/Results: Compounds 4, 6b, and 6c exhibited excellent in vitro antibacterial activities while compound 4 had the best antifungal activities. From the in silico antimicrobial results, compound 3 had a better binding affinity (-10.95 kcal/mol) than penicillin (-10.89 kcal/mol) while compounds 3 and 4 had binding affinities (-10.07 and -10.62kcal/mol) comparable to ketoconazole (-10.85 kcal/mol). Conclusion and implication: All the synthesized compounds exhibited significant antibacterial and antifungal activities and were confirmed to be potential antimicrobial agents.

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Section: Discussionmentioning

confidence: 99%

Design, synthesis, and molecular docking of cysteine-based sulphonamide derivatives as antimicrobial agents

et al. 2022

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“…Oxidative stress and microbial infections are related in their mode of in luence on the immune system (Kock et al, 1987). Generally, α-amino acids, when combined with sulphonamides, yield good anti-oxidants and antimicrobials (Egbujor et al, 2019a) , (Egbujor and Okoro, 2019) they are also known as the most excellent category of pharmacologically active amino acids (Young, 1994). It is expected that the utilization of α-amino acids in this study would achieve improved drug potency.…”

Section: Introductionmentioning

confidence: 93%

Synthesis, Molecular Docking and Pharmacological Investigation of Some 4-Methylphenylsulphamoyl Carboxylic Acid Analogs

Egbujor

Okoro

Okafor

et al. 2020

ijrps

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Compounds bearing and amino acid moieties are considered the basis for sulfa drug development. The synthesis of 4-methylphenylsulphamoyl acids and the evaluation of their pharmacological activities are reported. The synthesis of these compounds was accomplished by the reaction of various acids and 4-methyl chloride in basic aqueous solution. Structures were confirmed by FTIR, 1HNMR, 13CNMR spectra and elemental analytical data. Molecular docking interactions of the analogues were determined using PyRx. In the in antimicrobial activity analysis, compounds 1, 3, 5and 7 had antimicrobial inhibitory concentration range of 0.5-1.0mg/ml comparable with 0.1-2.0mg/ml of and . In the in anti-oxidant activity study compounds 1, 2and 6displayed half-maximal inhibitory concentrations (IC50) of 1.104±0.001 /ml, 1.159±0.002µg/ml and1.240±0.001µg/ml respectively comparable with 0.999±0.002µg/ml of acid. In the molecular docking study, compound 4 had a strong 2D binding interaction with II amino acid residue and compounds 1, 3, 4, 5, 6 and 7 had in antimicrobial, anti-oxidant, and antimalarial properties similar to their standard drugs. Considering the outstanding pharmacological properties and their strict compliance with Lipinski’s rule, the synthesized 4-methylphenylsulphamoyl analogues could be considered as antimicrobial, antimalarial, and anti-oxidant drug candidates.

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“…10iii) based on QSAR and pharmacophore models. Egbujor et al [112] reported a design and synthesis of α-amino acid-based sulphonamide derivative, 3-hydoxy-2-[(phenylsulfonyl)amino]propanoic acid (Fig. 10iv) having antioxidant activity comparable with ascorbic acid.…”

Section: Fig 9 5-hydroxypyrimidinementioning

confidence: 99%

Antioxidant Drug Design: Historical and Recent Developments

Egbujor

Egu

Okonkwo

et al. 2021

JPRI

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The sustained interest in the design of potent antioxidants drugs over the years can be attributed to the indispensable roles antioxidants play in the mitigation of oxidative stress and its concomitant diseases. The high demand for exogenous antioxidants has been ascribed to the prevalence of oxidative stress-mediated diseases such as cancer, diabetes, stroke, cell aging, arteriosclerosis and central nervous system disorders occasioned by a biochemical disequilibrium between the production of free radicals and the body’s ability to eliminate these reactive species from the biological system. COVID-19 severity and death have been linked to a free radical generating process known as the cytokine storm. In an attempt to maintain optimal body function, antioxidant supplementation has increasingly become a wide spread practice because of antioxidants’ ability to directly scavenge free radicals, inhibit oxidative chain reactions thereby increasing the antioxidant defenses of the body. Recent data showed that researchers had made significant efforts to demonstrate the importance and timeliness of antioxidant therapy based on drug design from natural and synthetic sources. Therefore this review presents antioxidant drug design methodologies, identifying the lead and hits to provide a historical and up-to-date collection of research briefs on antioxidant drug design into a single piece in order to ensure easy accessibility, motivate readership and inspire future researches.

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Design, synthesis, molecular docking, antimicrobial, and antioxidant activities of new phenylsulfamoyl carboxylic acids of pharmacological interest

Cited by 14 publications

References 12 publications

Design, synthesis, and molecular docking of cysteine-based sulphonamide derivatives as antimicrobial agents

Design, synthesis, and molecular docking of cysteine-based sulphonamide derivatives as antimicrobial agents

Synthesis, Molecular Docking and Pharmacological Investigation of Some 4-Methylphenylsulphamoyl Carboxylic Acid Analogs

Antioxidant Drug Design: Historical and Recent Developments

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