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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

Possible tautomeric structures of sulfonyl-carboximidamides
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Fig1: Possible tautomeric structures of sulfonyl-carboximidamides

Mentions: In the 1H NMR spectra of the target amidines the signals for all the protons of aromatic systems were observed and two signals for the NH groups were shifted from each other at about 1 ppm. These separated signals could be due to the amino-imine structure adopted by the obtained derivatives (Fig. 1, structure B), as suggested by Northey and co-workers [20]. They could also be the result of the magnetic inequivalence of NH protons in the amine moiety upon formation of a hydrogen bond in the case of heterocyclic compounds in which the amidine group is in the α position to the nitrogen atom of the heterocyclic ring (structure A), as shown in the previous article [21].Fig. 1


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)

Possible tautomeric structures of sulfonyl-carboximidamides
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

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

Fig1: Possible tautomeric structures of sulfonyl-carboximidamides
Mentions: In the 1H NMR spectra of the target amidines the signals for all the protons of aromatic systems were observed and two signals for the NH groups were shifted from each other at about 1 ppm. These separated signals could be due to the amino-imine structure adopted by the obtained derivatives (Fig. 1, structure B), as suggested by Northey and co-workers [20]. They could also be the result of the magnetic inequivalence of NH protons in the amine moiety upon formation of a hydrogen bond in the case of heterocyclic compounds in which the amidine group is in the α position to the nitrogen atom of the heterocyclic ring (structure A), as shown in the previous article [21].Fig. 1

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