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Synthesis, structure, and biological activity of novel heterocyclic sulfonyl-carboximidamides.

Gobis K, Foks H, Sławiński J, Sikorski A, Trzybiński D, Augustynowicz-Kopeć E, Napiórkowska A, Bojanowski K - Monatsh. Chem. (2013)

Bottom Line: New structures were confirmed by IR and NMR spectra as well as elemental analyses.Preliminary results indicated that target compounds exhibited weak tuberculostatic and antibacterial activities.Seven compounds inhibited the growth of some cancer cell lines, whereas one of the 2-quinoline derivatives displayed favorable activity against all tested cancer cells with GI 50 values of 0.92-13 μM.

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Medical University of Gdańsk, Gdańsk, Poland.

ABSTRACT

Abstract: A series of novel heterocyclic sulfonyl-carboximidamides were synthesized in satisfactory yields via condensation of heterocyclic methyl carbimidates with 2-chlorobenzenesulfonamide and 4-chloropyridine-3-sulfonamide. New structures were confirmed by IR and NMR spectra as well as elemental analyses. X-ray crystallography of two derivatives was performed. The single-crystal structures confirmed the presence of a primary amine group in the amidine moiety. All the compounds were screened for their tuberculostatic, antibacterial, and anticancer activities. Preliminary results indicated that target compounds exhibited weak tuberculostatic and antibacterial activities. Seven compounds inhibited the growth of some cancer cell lines, whereas one of the 2-quinoline derivatives displayed favorable activity against all tested cancer cells with GI 50 values of 0.92-13 μM.

No MeSH data available.


Related in: MedlinePlus

Total cell/protein count for compounds 1, 2, and 15
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Fig3: Total cell/protein count for compounds 1, 2, and 15

Mentions: The most antibacterially potent sulfonylcarboximidamides 1, 2, and 15 were then tested for their effects on the proliferation of neonatal human dermal fibroblasts (ATCC PCS-201-010). MAP (magnesium ascorbyl phosphate) and bFGF (basic fibroblast growth factor) were used as the positive control (Fig. 3). Compound 2 had no cytotoxic activity. Irrespective to the compound concentration the cell growth remained at the level corresponding to the water-treated control. Compound 1 had a weak inhibitory activity. For low compound concentrations (6.25–12.5 μg/cm3) no cytotoxic effect was evident. In the range 25–100 μg/cm3 a linear relation of the cytotoxic effect was observed with an 88 % growth inhibitory activity at a concentration of 100 μg/cm3. Compound 15 was strongly cytotoxic, even at the lowest concentration tested (6.25 μg/cm3—70 % growth inhibitory activity).Fig. 3


Synthesis, structure, and biological activity of novel heterocyclic sulfonyl-carboximidamides.

Gobis K, Foks H, Sławiński J, Sikorski A, Trzybiński D, Augustynowicz-Kopeć E, Napiórkowska A, Bojanowski K - Monatsh. Chem. (2013)

Total cell/protein count for compounds 1, 2, and 15
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4494771&req=5

Fig3: Total cell/protein count for compounds 1, 2, and 15
Mentions: The most antibacterially potent sulfonylcarboximidamides 1, 2, and 15 were then tested for their effects on the proliferation of neonatal human dermal fibroblasts (ATCC PCS-201-010). MAP (magnesium ascorbyl phosphate) and bFGF (basic fibroblast growth factor) were used as the positive control (Fig. 3). Compound 2 had no cytotoxic activity. Irrespective to the compound concentration the cell growth remained at the level corresponding to the water-treated control. Compound 1 had a weak inhibitory activity. For low compound concentrations (6.25–12.5 μg/cm3) no cytotoxic effect was evident. In the range 25–100 μg/cm3 a linear relation of the cytotoxic effect was observed with an 88 % growth inhibitory activity at a concentration of 100 μg/cm3. Compound 15 was strongly cytotoxic, even at the lowest concentration tested (6.25 μg/cm3—70 % growth inhibitory activity).Fig. 3

Bottom Line: New structures were confirmed by IR and NMR spectra as well as elemental analyses.Preliminary results indicated that target compounds exhibited weak tuberculostatic and antibacterial activities.Seven compounds inhibited the growth of some cancer cell lines, whereas one of the 2-quinoline derivatives displayed favorable activity against all tested cancer cells with GI 50 values of 0.92-13 μM.

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Medical University of Gdańsk, Gdańsk, Poland.

ABSTRACT

Abstract: A series of novel heterocyclic sulfonyl-carboximidamides were synthesized in satisfactory yields via condensation of heterocyclic methyl carbimidates with 2-chlorobenzenesulfonamide and 4-chloropyridine-3-sulfonamide. New structures were confirmed by IR and NMR spectra as well as elemental analyses. X-ray crystallography of two derivatives was performed. The single-crystal structures confirmed the presence of a primary amine group in the amidine moiety. All the compounds were screened for their tuberculostatic, antibacterial, and anticancer activities. Preliminary results indicated that target compounds exhibited weak tuberculostatic and antibacterial activities. Seven compounds inhibited the growth of some cancer cell lines, whereas one of the 2-quinoline derivatives displayed favorable activity against all tested cancer cells with GI 50 values of 0.92-13 μM.

No MeSH data available.


Related in: MedlinePlus