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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.


Synthesis of N-(2,6-dimethoxypyrimidin-4-yl)-4-isothiocyanato-benzenesulfonamide 2
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Sch1: Synthesis of N-(2,6-dimethoxypyrimidin-4-yl)-4-isothiocyanato-benzenesulfonamide 2

Mentions: Isothiocyanates are useful and widely used building blocks in the synthesis of nitrogen, sulfur and oxygen heterocycles and organometallic compounds of academic, pharmaceutical and industrial interest [36]. The high electrophilicity and nucleophilicity associated with the carbon and sulfur atoms, respectively, of the isothiocyanates and their extended π electron system make them unique precursors of a large variety of target molecules. Consequently, many classes of five and six-membered nitrogen and sulfur heterocycles, either carrying various substituents or fused with benzo or non-benzo nuclei to interesting poly heterocycles, have been synthesized from isothiocyanates which is undoubtedly a landmark in organosulfur chemistry [37]. The intermediate, N-(2,6-dimethoxypyrimidin-4-yl)-4-isothiocyanatobenzenesulfonamide 2 used for the preparation of target compounds have been synthesized in high yield via thiophosgenation of sulfa-dimethoxazine 1 at room temperature in the presence of dilute hydrochloric acid, according to literature procedure [38] (Scheme 1).Scheme 1


Antimicrobial and anticancer activity of some novel fluorinated thiourea derivatives carrying sulfonamide moieties: synthesis, biological evaluation and molecular docking
Synthesis of N-(2,6-dimethoxypyrimidin-4-yl)-4-isothiocyanato-benzenesulfonamide 2
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

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

Sch1: Synthesis of N-(2,6-dimethoxypyrimidin-4-yl)-4-isothiocyanato-benzenesulfonamide 2
Mentions: Isothiocyanates are useful and widely used building blocks in the synthesis of nitrogen, sulfur and oxygen heterocycles and organometallic compounds of academic, pharmaceutical and industrial interest [36]. The high electrophilicity and nucleophilicity associated with the carbon and sulfur atoms, respectively, of the isothiocyanates and their extended π electron system make them unique precursors of a large variety of target molecules. Consequently, many classes of five and six-membered nitrogen and sulfur heterocycles, either carrying various substituents or fused with benzo or non-benzo nuclei to interesting poly heterocycles, have been synthesized from isothiocyanates which is undoubtedly a landmark in organosulfur chemistry [37]. The intermediate, N-(2,6-dimethoxypyrimidin-4-yl)-4-isothiocyanatobenzenesulfonamide 2 used for the preparation of target compounds have been synthesized in high yield via thiophosgenation of sulfa-dimethoxazine 1 at room temperature in the presence of dilute hydrochloric acid, according to literature procedure [38] (Scheme 1).Scheme 1

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.