Synthesis and characterization of novel sulfonamides derivatives and their  antimicrobial, antioxidant and cytotoxicity evaluation

Rehman, Habib ur; Qadir, Abdul; Ali, Zeyan Abdullah; Nazir, Sajidah Parveen and Hafsa and Imran Nazir Sajidah Parveen and Hafsa and Imran; Zahra, Asmat; Shahzady, Tanzeela Gulab

doi:10.4314/bcse.v31i3.13

Cited by 12 publications

(12 citation statements)

References 12 publications

(10 reference statements)

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“…4-(4′-Nitrophenyl)- N -tosylthiazol-2-amine ( 11a ) and 4-(4′-nitrophenyl)- N -benzenesulfonylthiazol-2-amine ( 11b ) were synthesized by electrophilic substitution reaction [ 22 ]. Compound 7 was reacted with benzene sulfonyl chloride/toluene sulfonyl chloride in methanol and the mixture was basified by dry pyridine to afford compound 11a , 11b with 81%, and 72% yield, respectively [ 26 ].…”

Section: Resultsmentioning

confidence: 99%

“…Sulfathiazole derivatives (11a-b) were synthesized according to protocol developed by Rehman et al, [ 22 ]. The intermediate 4-(4′-nitro phenyl) thiazol-2-amine (7) (4 mmol) was poured directly into 4 mmol of benzene/toluene sulfonyl chloride ( 8/9) , in the presence of pyridine (3 ml) in 40 mL of methanol for 24 hr at 25°C as represented in Scheme 2 .…”

Section: Methodsmentioning

confidence: 99%

“…Sulfathiazole derivatives (11a-b) were synthesized according to protocol developed by Rehman et al,[22].…”

Section: Synthesis Of Sulfathiazole Derivatives (11a-b)mentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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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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“…The lowest concentration inhibiting growth of the organism is recorded as the MIC. The amount of growth from the control tube before incubation is compared [23].…”

Section: Determination Of Minimal Inhibition Concentrations By Micro mentioning

confidence: 99%

Aqueous phase synthesis, crystal structure and antimicrobial activity of 4-(substituted phenylazo)-3-methyl-4H-isoxazol-5-one azo dyes

Banpurkar¹,

Wazalwar²,

Perdih³

2018

Bull. Chem. Soc. Eth.

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3-Methyl-4H-isoxazol-5-one was synthesized at room temperature by simple stirring method from ethyl acetoacetate and hydroxylamine hydrochloride in aqueous medium and coupled with diazotized substituted amine to form series of 4-(substituted phenylazo)-3-methyl-4H-isoxazol-5-ones through green chemistry. All the compounds formed were characterized by IR, 1 H and 13 C NMR spectroscopy, MS and elemental analysis. Crystal structure of novel 4-(4-fluorophenylazo)-3-methyl-4H-isoxazol-5-one was determined by the X-ray diffraction. Antibacterial and antifungal activity was studied against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Staphylococcus pyogenus and Candida albicans, Aspergillus niger, Aspergillus clavatus, respectively. All synthesized compounds were found to be active against a gram-positive bacterium Staphylococcus aureus. Two compounds showed antifungal activity against Candida albicans close to standard greseofulvin.

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“…[15][16][17] SN derivatives are an important class of drugs used in clinics as pharmacological agents such as anti-bacterial, anti-tumor, anti-thyroid, anti-fungal, anti-inflammatory, anti-obesity, etc. [18] Recent use of SNs includes anti-cancer, antiviral HIV (HIV protease inhibitors, non-nucleoside HIV reverse transcriptase or HIV integrase inhibitors), [19][20][21] and Alzheimer's disease [22] agents. Such properties of SN drugs are likely due to the presence of -SO 2 NH-(or -OSO 2 NH-, -NHSO 2 NH-) moieties which can react with metal ions or bio-macromolecules like amino acid residues in proteins and DNA or RNA acting as drug targets.…”

Section: Introductionmentioning

confidence: 99%

Lysozyme binding with sulfa group of antibiotics: Comparative binding thermodynamics and computational study

2022

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Protein-drug binding study addresses a broad domain of biological problems associating molecular functions to physiological processes composing and modifying safe and coherent drug therapeutics. Comparison of the binding and thermodynamic aspect of sulfa drugs, sulfamethazine (SMZ) and sulfadiazine (SDZ) with the protein, lysozyme (Lyz) was carried out using spectroscopic, molecular docking, and dynamic simulation studies. The fluorescence quenching and apparent binding constant for the binding reaction were calculated to be in the order of 10 4 M À1 , slightly higher for SMZ as compared to that of SDZ and the binding stoichiometry values show 1:1 drug binding with each protein molecule. The binding was an enthalpy-driven spontaneous exothermic reaction favored by a negative enthalpy and a positive entropy contribution for both the complexes. The binding from the fluorescence quenching data suggests a static quenching mechanism dominated by non-polyelectrolytic components. Synchronous fluorescence denoted a conformational change in the tryptophan moiety of the protein. Molecular docking and dynamic simulation study provided a clearer view of the interaction pattern, where the drug resides on the binding pocket of the protein structure. Overall the protein, Lyz binding of SMZ was slightly more favored over SDZ.

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Synthesis and characterization of novel sulfonamides derivatives and their antimicrobial, antioxidant and cytotoxicity evaluation

Cited by 12 publications

References 12 publications

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

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

Aqueous phase synthesis, crystal structure and antimicrobial activity of 4-(substituted phenylazo)-3-methyl-4H-isoxazol-5-one azo dyes

Lysozyme binding with sulfa group of antibiotics: Comparative binding thermodynamics and computational study

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