Synthesis, Characterization and Study Biological Activity of New Para-methoxy Benzene Sulfonamide Derivatives and some Amino Acid

Awad, Sana Hitur; Sahib, S. A.; Hussein, Fatimah Ali; Al-Khfaji, Hussein Abdulkadhim Hasan

doi:10.1088/1757-899x/571/1/012093

Cited by 2 publications

(2 citation statements)

References 7 publications

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“…From 1950s till the present day, the synthesis of more potent high-profile sulpha drugs is still in progress. These include the antibacterial agent, sulphathiazole 12 [16], the carbonic anhydrase inhibitor, acetazolamide 13 [17] [18] which has been in use clinically for more than 45 years, the diuretic agent, Furosemide 14 [19] the hypoglycemic agent glibenclamide 15 [20], the anticancer sulphonamide, indisulam 16 [21], the aspartic HIV protease inhibitor amprenavir 17 [22] used for AIDS and HIV infection management and the metalloprotease (MMP) inhibitors 18 of the sulphonyl amino acid hydroxamate [23] just to mention but a few (Figure 5).…”

Section: A C C E P T E D Mmentioning

confidence: 99%

Preparation, Characterization, In silico and In vitro Antimicrobial Studies of Phenothiazine-3-sulphonamide Derivatives

Ayuk,

Uchegbu,

Ebiem-Kenechukwu

et al. 2024

Bioactivities

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The antibacterial activities of phenothiazine and sulphonamide derivatives have attracted so much interest. In this study, the synthesis and characterization of phenothiazine-3-sulphonamide derivatives and evaluation of their antimicrobial activity against the following pathogenic microorganisms is reported. Two Gram-positive bacteria; (Staphylococcus aureus (ATCC: 6538) and Streptococcus pyogenes (ATCC: 27853)), two Gram-negative bacteria; (Escherichia coli(ATCC: 3008), and Salmonella typhi (ATCC: 25175)) as well as one fungus (Aspergillus fumigatus (ATCC: 10231)) were used while ciprofloxacin, gentamycin and ketoconazole served as standard drugs. The synthesis of the derivatives was achieved through a base catalyzed the reaction of 4-chloroaniline with 1-naphthylamine to form 1-(naphthalen-1-yl)benzene-1,4-diamine. This intermediate was then treated with sulphur and iodine to yield the phenothiazine derivative while subsequent treatment of the phenothiazine compound with sulphonyl chlorides gave the final products. The synthesized compounds were characterized via proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR) and Fourier-transform infrared (FTIR) spectroscopic techniques. The minimum inhibitory concentration (MIC) of each compound was then determined using the agar well diffusion method. To predict the binding energies and patterns of the synthesized compounds with target proteins of the above-mentioned microorganisms, molecular docking simulations were run using Autodock Vina software (version 4.2). The spectra data of the compounds for FTIR, 1H-NMR and 13C-NMR spectral data were consistent with the assigned structures of the synthesized compounds. The binding energies (kcal/mol) for in silico antimicrobial studies were in the range -5.1 to -7.6 kcal/mol. The MIC values were in the range 3.5 to 1.0 mg/L. The results of the in vitro test revealed that the synthesized compounds exhibit promising antimicrobial activity and showed excellent bactericidal and fungicidal activities. The results obtained showed that the synthesized compounds possess drug-like properties and are good starting materials for drug production.

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Section: A C C E P T E D Mmentioning

confidence: 99%

Preparation, Characterization, In silico and In vitro Antimicrobial Studies of Phenothiazine-3-sulphonamide Derivatives

Ayuk,

Uchegbu,

Ebiem-Kenechukwu

et al. 2024

Bioactivities

View full text Add to dashboard Cite

show abstract

“…From 1950s till the present day, more potent high-profile sulpha drugs are being produced. These include the antibacterial agent, sulphathiazole 12 [16], the carbonic anhydrase inhibitor, acetazolamide 13 [17,18] which has been in use clinically for more than 45 years, the diuretic agent, Furosemide 14 [19] the hypoglycemic agent glibenclamide 15 [20], the anticancer sulphonamide, indisulam 16 [21], the aspartic HIV protease inhibitor amprenavir 17 [22] used for AIDS and HIV infection management and the metalloprotease (MMP) inhibitors 18 of the sulphonyl amino acid hydroxamate [23] just to mention but a few (Figure 5) Studies have shown that the presence of folate (folic acid) 22 is very vital in the manufacture of nucleic acids present in the cell wall of bacteria [24] while its absence renders the cells inactive and prevent DNA synthesis. This can be seen when sulphonamide 8 reacts with dihydropteridine diphosphate 19 to form dihydropteroic sulphonamide 23 in the path way B (scheme 1) [25] which hinders further reaction for the formation of folic acid.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, In silico and In vitro Antimicrobial Activity of Phenothiazine-3-sulphonamide Derivatives

Ayuk,

Uchegbu,

Aronimo

et al. 2024

Preprint

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The numerous biological activities of phenothiazine and sulphonamide derivatives, especially their antibacterial qualities, have attracted so much interest. In this study, the synthesis and characterization of phenothiazine-3-sulphonamide derivatives and evaluation their antimicrobial activity against the following pathogenic microorganisms is reported. Two gram-positive bacteria; (Staphylococcus aureus, and Streptococcus pyogenes), two gram-negative bacteria; (Escherichia coli, and Salmonella typhi) as well as one fungus (Aspergillus fumigatus) were used while ciprofloxacin, gentamycin and ketoconazole served as standard drugs. The synthesis of the derivatives was achieved through a base catalyzed the reaction of 4-chloroaniline with 1-naphthylamine to form 1-(naphthalen-1-yl) benzene-1,4-diamine. This intermediate was then treated with sulphur and iodine to yield the phenothiazine derivative while subsequent treatment of the phenothiazine compound with sulphonyl chlorides gave the final products. The synthesized compounds were characterized via proton nuclear magnetic resonance (1HNMR), carbon-13 nuclear magnetic resonance (13C NMR) and Fourier-transform infrared (FTIR) spectroscopic techniques. The minimum inhibitory concentration (MIC) of each compound was then determined using the agar well diffusion method. To predict the binding energies and patterns of the synthesized compounds with target proteins of the above mentioned microorganisms, molecular docking simulations were run using Autodock Vina software (version 4.2). The spectra data of the compounds for FTIR, 1H NMR and 13C NMR (δ) spectral data were consistent with the assigned structures of the synthesized compounds. The binding energies (kcal/mol) for in silico antimicrobial studies were in the range -5.1 to -7.6 kcal/mol. The MIC values were in the range -3.5 to 1.0 mg/L. The results of the in vitro test revealed that the synthesized compounds exhibits promising antimicrobial activity, and showed excellent bactericidal and fungicidal activities. The results obtained showed that the synthesized compounds possess drug-like properties and are good starting materials for drug production.

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Synthesis, Characterization and Study Biological Activity of New Para-methoxy Benzene Sulfonamide Derivatives and some Amino Acid

Cited by 2 publications

References 7 publications

Preparation, Characterization, In silico and In vitro Antimicrobial Studies of Phenothiazine-3-sulphonamide Derivatives

Preparation, Characterization, In silico and In vitro Antimicrobial Studies of Phenothiazine-3-sulphonamide Derivatives

Synthesis, Characterization, In silico and In vitro Antimicrobial Activity of Phenothiazine-3-sulphonamide Derivatives

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