Biological evaluation of some new N -(2,6-dimethoxypyrimidinyl) thioureido benzenesulfonamide derivatives as potential antimicrobial and anticancer agents

Ghorab, Mostafa M.; Alsaid, Mansour S.; El‐Gaby, Mohamed S. A.; Safwat, Nesreen A.; Elaasser, Mahmoud M.; Soliman, Aiten M.

doi:10.1016/j.ejmech.2016.08.060

Cited by 81 publications

(44 citation statements)

References 36 publications

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“…The thiocarbonyl group of the thiourea moiety was also observed in the 13 C-NMR spectrum. The formation of thioureas 3a – t can be explained through the previously reported mechanism [24]. …”

Section: Resultsmentioning

confidence: 91%

“…For the above-mentioned reasons and as a part of our interest in the synthesis and screening of potentially bioactive compounds [20–24], we herein, report the synthesis of some novel N -(2,6-dimethoxypyrimidin-4-yl)-4-(3-(aryl)thioureido)benzenesulfonamides 3a – t to be evaluated for their antimycobacterial activity. The promising compounds 3i and 3s were docked inside the active site of M. tuberculosis enoyl reductase InhA, to predict their possible mode of action.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, docking study and biological evaluation of some new thiourea derivatives bearing benzenesulfonamide moiety

Ghorab

El‐Gaby

Soliman

et al. 2017

Chemistry Central Journal

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BackgroundA series of novel N-(2, 6-dimethoxypyrimidin-4-yl)-4-(3-(aryl)thioureido) benzenesulfonamides 3a–t was synthesized by the addition of N-(2,6-dimethoxypyrimidin-4-yl)-4-isothiocyanatobenzenesulfonamide 2 to the appropriate aromatic amine. The structures of the synthesized compounds were inspired from the second line antituberculosis pro-drugs.ResultsMost of the new compounds were screened for their activity against Mycobacterium tuberculosis. The results of the antimycobacterial assay showed that compound 3i exerted the highest activity (MIC = 3.13 µg/mL), followed by compound 3s (MIC = 6.25 µg/mL).ConclusionThe structure–activity relationship (SAR) analysis revealed that the introduction of the benzo[1,3]dioxol moiety in 3i and the 4-morpholinyl-4-phenyl moiety in 3s has proven to give the most potent compounds in this study. Docking of the promising compounds inside the active site of M. tuberculosis enoyl reductase InhA was performed in order to emphasize the results. The compounds showed a similar orientation to that of GSK 625 inside the active site of 5JFO and bind to Met 98 in a way similar to that of the co-crystallized ligand.

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Section: Resultsmentioning

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Synthesis, docking study and biological evaluation of some new thiourea derivatives bearing benzenesulfonamide moiety

Ghorab

El‐Gaby

Soliman

et al. 2017

Chemistry Central Journal

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“…DMSO was used for dissolving the tested compounds thus used as solvent control and showed no inhibition zones, conirming that it has no in luence on growth of the tested microorganisms. Positive controls were also performed using Amoxicillin as standard antibacterial drugs and Nystatin as standard antifungal drug y (Mastoura et al, 2018;Ghorab et al, 2016).…”

Section: Biological Activity Testmentioning

confidence: 99%

Triazoles with long chain alkyl groups as a potential biological compounds

Salman¹

2019

ijrps

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New series of four compounds was synthesized from multi hydroxyl group compounds such as methyl glycoside by coupling with long-chain alky propargyl ester ( C10, C12, C14 and unsaturated C18) via click chemistry after activation the hydroxyl at C6 position by chlorination with N-chlorosuccinimide NCS and functionalized with sodium azide NaN3. The chemical structures and the purity of the resulting triazoles derivatives was confirmed by elemental analysis (CHN) and spectroscopic analysis 1H NMR & 13C NMR. The biological activity for the target compounds was investigated, and they show good antibacterial and antifungal properties against some selected gram-posative and fungi, which make them suitable for medical applications.

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“…In the field of medical chemistry, thiourea derivatives are of great interest due to their synthetic utility and biological importance. The thiourea moiety is a structural part of many bioactive compounds, that display antimicrobial [ 1 , 2 , 3 , 4 , 5 ], antifungal [ 6 ], antitubercular [ 2 , 7 , 8 ], antiviral [ 9 , 10 , 11 , 12 ], and central nervous system stimulating [ 13 , 14 , 15 , 16 ] properties. Derivatives of this group are also viewed as one of the most promising classes of anticancer agents.…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand, bis-thiazoles derived from disubstituted thioureas are supposed to be involved in the regulation of the expression of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), overexpressed in pathological conditions; e.g., cancer [ 20 ]. Another group, thioureido benzenesulfonamide derivatives, was found to inhibit carbonic anhydrase CA IX, which triggers the migration of tumor cells and results in a raise of the aggressive/invasive phenotype of cancer [ 6 ]. Pyrimidinyl acyl thioureas have shown the ability to block Heat Shock Protein 90 (Hsp90) ATP binding site [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

Disubstituted 4-Chloro-3-nitrophenylthiourea Derivatives: Antimicrobial and Cytotoxic Studies

et al. 2018

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4-Chloro-3-nitrophenylthioureas 1–30 were synthesized and tested for their antimicrobial and cytotoxic activities. Compounds exhibited high to moderate antistaphylococcal activity against both standard and clinical strains (MIC values 2–64 μg/mL). Among them derivatives with electron-donating alkyl substituents at the phenyl ring were the most promising. Moreover, compounds 1–6 and 8–19 were cytotoxic against MT-4 cells and various other cell lines derived from human hematological tumors (CC50 ≤ 10 μM). The influence of derivatives 11, 13 and 25 on viability, mortality and the growth rate of immortalized human keratinocytes (HaCaT) was observed.

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Biological evaluation of some new N -(2,6-dimethoxypyrimidinyl) thioureido benzenesulfonamide derivatives as potential antimicrobial and anticancer agents

Cited by 81 publications

References 36 publications

Synthesis, docking study and biological evaluation of some new thiourea derivatives bearing benzenesulfonamide moiety

Synthesis, docking study and biological evaluation of some new thiourea derivatives bearing benzenesulfonamide moiety

Triazoles with long chain alkyl groups as a potential biological compounds

Disubstituted 4-Chloro-3-nitrophenylthiourea Derivatives: Antimicrobial and Cytotoxic Studies

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