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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

Structure of 3 (a) and 4 (b) showing 25 % probability displacements for ellipsoid. H atoms shown as small spheres of arbitrary radius. The arrangement of the molecules in the crystal structure of 3 (c) and 4 (d) viewed along b axis. Dashed lines N–H···O, N–H···N, C–H···Cl, and C–H···O interactions
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Fig2: Structure of 3 (a) and 4 (b) showing 25 % probability displacements for ellipsoid. H atoms shown as small spheres of arbitrary radius. The arrangement of the molecules in the crystal structure of 3 (c) and 4 (d) viewed along b axis. Dashed lines N–H···O, N–H···N, C–H···Cl, and C–H···O interactions

Mentions: Such a structure could also be stabilized by hydrogen bonding between the second proton of the amine group and the oxygen atom of the sulfonyl moiety. This issue was resolved by X-ray studies performed on derivatives 3 and 4. The obtained results revealed the tautomeric structure A (Fig. 2a, b). Thus, formation of hydrogen bonds is the reason for the magnetic inequivalence of the protons of the amino group and separate signals in the 1H NMR spectra of the synthesized compounds.Fig. 2


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)

Structure of 3 (a) and 4 (b) showing 25 % probability displacements for ellipsoid. H atoms shown as small spheres of arbitrary radius. The arrangement of the molecules in the crystal structure of 3 (c) and 4 (d) viewed along b axis. Dashed lines N–H···O, N–H···N, C–H···Cl, and C–H···O interactions
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

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

Fig2: Structure of 3 (a) and 4 (b) showing 25 % probability displacements for ellipsoid. H atoms shown as small spheres of arbitrary radius. The arrangement of the molecules in the crystal structure of 3 (c) and 4 (d) viewed along b axis. Dashed lines N–H···O, N–H···N, C–H···Cl, and C–H···O interactions
Mentions: Such a structure could also be stabilized by hydrogen bonding between the second proton of the amine group and the oxygen atom of the sulfonyl moiety. This issue was resolved by X-ray studies performed on derivatives 3 and 4. The obtained results revealed the tautomeric structure A (Fig. 2a, b). Thus, formation of hydrogen bonds is the reason for the magnetic inequivalence of the protons of the amino group and separate signals in the 1H NMR spectra of the synthesized compounds.Fig. 2

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