Limits...
Antimicrobial and anticancer activity of some novel fluorinated thiourea derivatives carrying sulfonamide moieties: synthesis, biological evaluation and molecular docking

View Article: PubMed Central

ABSTRACT

Background: Various thiourea derivatives have been used as starting materials for compounds with better biological activities. Molecular modeling tools are used to explore their mechanism of action.

4a4c4d4a: A new series of thioureas were synthesized. Fluorinated pyridine derivative showed the highest antimicrobial activity (with MIC values ranged from 1.95 to 15.63 µg/mL). Interestingly, thiadiazole derivative and coumarin derivative exhibited selective antibacterial activities against Gram positive bacteria. Fluorinated pyridine derivative was the most active against HepG2 with IC50 value of 4.8 μg/mL. Molecular docking was performed on the active site of MK-2 with good results.

4a: Novel compounds were obtained with good anticancer and antibacterial activity especially fluorinated pyridine derivative and molecular docking study suggest good activity as mitogen activated protein kinase-2 inhibitor.

No MeSH data available.


The proposed mechanism for the formation of thiourea
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

License 1 - License 2
getmorefigures.php?uid=PMC5383913&req=5

Fig2: The proposed mechanism for the formation of thiourea

Mentions: The synthesis of N-(2,6-dimethoxypyrimidin-4-yl)-4-(3-(aryl) thio-ureido)benzenesulfonamides 3a–e is outlined in Scheme 2. Treatment of isothiocyanato benzenesulfonamide 2 with a variety of fluorinated aromatic amines in dry dioxane at reflux temperature in the presence of a catalytic amounts of triethylamine furnished the novel fluorinated N,N-disubstituted thioureas 3a–e in high yields (80–92%).The structure of the products 3a–e were established via inspection of their spectral data. Thioureas 3a–e were confirmed by the absence of characteristic infrared absorption peak at 2000–2200 cm−1 (N=C=S group). Also, the infrared of 3 is characterized by the presence of the NH, CN, thiocarbonyl (CS) and SO2 absorption bands. For example, the 1H NMR of compound 3a showed two singlets at δ 3.81, 3.84 ppm which were assigned for two methoxy protons, a singlet at δ 5.9 ppm assigned to the pyrimidine-H, two downfield singlets at δ 11.8, and 14.0 ppm which were readily assigned to the HN(1) and HN(2) protons, in addition to the presence of SO2NH and aromatic protons. The thiocarbonyl group of thiourea moiety was also observed in 13C-NMR. The formation of thiourea 3a–e can be explained by the reaction pathway depicted in Fig. 2.Scheme 2


Antimicrobial and anticancer activity of some novel fluorinated thiourea derivatives carrying sulfonamide moieties: synthesis, biological evaluation and molecular docking
The proposed mechanism for the formation of thiourea
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC5383913&req=5

Fig2: The proposed mechanism for the formation of thiourea
Mentions: The synthesis of N-(2,6-dimethoxypyrimidin-4-yl)-4-(3-(aryl) thio-ureido)benzenesulfonamides 3a–e is outlined in Scheme 2. Treatment of isothiocyanato benzenesulfonamide 2 with a variety of fluorinated aromatic amines in dry dioxane at reflux temperature in the presence of a catalytic amounts of triethylamine furnished the novel fluorinated N,N-disubstituted thioureas 3a–e in high yields (80–92%).The structure of the products 3a–e were established via inspection of their spectral data. Thioureas 3a–e were confirmed by the absence of characteristic infrared absorption peak at 2000–2200 cm−1 (N=C=S group). Also, the infrared of 3 is characterized by the presence of the NH, CN, thiocarbonyl (CS) and SO2 absorption bands. For example, the 1H NMR of compound 3a showed two singlets at δ 3.81, 3.84 ppm which were assigned for two methoxy protons, a singlet at δ 5.9 ppm assigned to the pyrimidine-H, two downfield singlets at δ 11.8, and 14.0 ppm which were readily assigned to the HN(1) and HN(2) protons, in addition to the presence of SO2NH and aromatic protons. The thiocarbonyl group of thiourea moiety was also observed in 13C-NMR. The formation of thiourea 3a–e can be explained by the reaction pathway depicted in Fig. 2.Scheme 2

View Article: PubMed Central

ABSTRACT

Background: Various thiourea derivatives have been used as starting materials for compounds with better biological activities. Molecular modeling tools are used to explore their mechanism of action.

4a4c4d4a: A new series of thioureas were synthesized. Fluorinated pyridine derivative showed the highest antimicrobial activity (with MIC values ranged from 1.95 to 15.63 µg/mL). Interestingly, thiadiazole derivative and coumarin derivative exhibited selective antibacterial activities against Gram positive bacteria. Fluorinated pyridine derivative was the most active against HepG2 with IC50 value of 4.8 μg/mL. Molecular docking was performed on the active site of MK-2 with good results.

4a: Novel compounds were obtained with good anticancer and antibacterial activity especially fluorinated pyridine derivative and molecular docking study suggest good activity as mitogen activated protein kinase-2 inhibitor.

No MeSH data available.