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

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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.


Synthetic route and structures for thiourea derivatives (4a–d)
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Sch3: Synthetic route and structures for thiourea derivatives (4a–d)

Mentions: The nucleophilic attack of the amino group of the aromatic amine on thiocarbonyl group of isothiocyanate leads to formation of an intermediate (A). During the consecutive steps, deprotonation and protonation of the intermediate results in the formation of the final product thiourea. Under similar reaction conditions, treatment of isothiocyanate 2 with fluorinated heterocyclic amines such as 2-amino-2,3,5,6-tetrafluoropyridine, 2-amino-6-fluorobenzothiazole, 2-amino-5-(trifluoromethyl)-1,3,4-thiadiazole and 7-amino-4-(trifluoromethyl)-coumarine afforded the corresponding fluorinated heterocyclic thioureas 4a–d, (Scheme 3). The composition and structure of products 4a–d were confirmed by the results of elemental analysis and data of IR and NMR spectra. The infrared of structure 4 displayed absorption band assignable for NH, thiocarbonyl (CS) and SO2 groups. The infrared of 4c exhibited stretching frequencies at 3415, 3310, 2978, 2841 and 1618 cm−1 for the two NH, CH-aliph and CN groups, in addition to the presence of absorption bands corresponding to SO2 and CS at 1311, 1195, 1274 cm−1. Its 1H NMR showed two singlets at δ 3.64, 3.66 ppm which were assigned for two methoxy protons, a singlet at δ 6.5 ppm assigned to the pyrimidine-H, two downfield singlets at δ 11.8, and 12.4 ppm which were readily assigned to the HN(1) and HN(2) protons, in addition to the presence of SO2NH and aromatic protons (Scheme 3).Scheme 3


Antimicrobial and anticancer activity of some novel fluorinated thiourea derivatives carrying sulfonamide moieties: synthesis, biological evaluation and molecular docking
Synthetic route and structures for thiourea derivatives (4a–d)
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

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

Sch3: Synthetic route and structures for thiourea derivatives (4a–d)
Mentions: The nucleophilic attack of the amino group of the aromatic amine on thiocarbonyl group of isothiocyanate leads to formation of an intermediate (A). During the consecutive steps, deprotonation and protonation of the intermediate results in the formation of the final product thiourea. Under similar reaction conditions, treatment of isothiocyanate 2 with fluorinated heterocyclic amines such as 2-amino-2,3,5,6-tetrafluoropyridine, 2-amino-6-fluorobenzothiazole, 2-amino-5-(trifluoromethyl)-1,3,4-thiadiazole and 7-amino-4-(trifluoromethyl)-coumarine afforded the corresponding fluorinated heterocyclic thioureas 4a–d, (Scheme 3). The composition and structure of products 4a–d were confirmed by the results of elemental analysis and data of IR and NMR spectra. The infrared of structure 4 displayed absorption band assignable for NH, thiocarbonyl (CS) and SO2 groups. The infrared of 4c exhibited stretching frequencies at 3415, 3310, 2978, 2841 and 1618 cm−1 for the two NH, CH-aliph and CN groups, in addition to the presence of absorption bands corresponding to SO2 and CS at 1311, 1195, 1274 cm−1. Its 1H NMR showed two singlets at δ 3.64, 3.66 ppm which were assigned for two methoxy protons, a singlet at δ 6.5 ppm assigned to the pyrimidine-H, two downfield singlets at δ 11.8, and 12.4 ppm which were readily assigned to the HN(1) and HN(2) protons, in addition to the presence of SO2NH and aromatic protons (Scheme 3).Scheme 3

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.