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Synthesis, structure, and antimicrobial activity of heterocyclic phenylsulfonyl- and 4-aminophenylsulfonyl-carboximidamides.

Gobis K, Foks H, Wiśniewska K, Dąbrowska-Szponar M, Augustynowicz-Kopeć E, Napiórkowska A, Sikorski A - Monatsh. Chem. (2012)

Bottom Line: A series of novel phenylsulfonyl- and 4-aminophenylsulfonyl-carboximidamides were synthesized by condensation of sulfonamides with heterocyclic methyl carbimidates obtained from heterocyclic carbonitriles and used 'at its inception.' The molecular structure of the obtained compounds is discussed.Compounds possessing heterocyclic systems with a nitrogen atom in the α position to the functional group showed a different single-crystal structure than expected.The synthesized derivatives were evaluated for antimicrobial activities: tuberculostatic, antibacterial, and antifungal. .

View Article: PubMed Central - PubMed

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

ABSTRACT

Abstract: A series of novel phenylsulfonyl- and 4-aminophenylsulfonyl-carboximidamides were synthesized by condensation of sulfonamides with heterocyclic methyl carbimidates obtained from heterocyclic carbonitriles and used 'at its inception.' The molecular structure of the obtained compounds is discussed. Compounds possessing heterocyclic systems with a nitrogen atom in the α position to the functional group showed a different single-crystal structure than expected. The synthesized derivatives were evaluated for antimicrobial activities: tuberculostatic, antibacterial, and antifungal.

Graphical abstract: .

No MeSH data available.


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Structure of N′-(4-aminophenylsulfonyl)-4-chloropicolinimidamide showing 25 % probability displacements for ellipsoids. H atoms are shown as small spheres of arbitrary radius (intramolecular N–H···O and N–H···N interactions are represented by dashed lines)
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Fig2: Structure of N′-(4-aminophenylsulfonyl)-4-chloropicolinimidamide showing 25 % probability displacements for ellipsoids. H atoms are shown as small spheres of arbitrary radius (intramolecular N–H···O and N–H···N interactions are represented by dashed lines)

Mentions: The study also resolved the molecular structure of the products of the reaction between carbimidates and 4-aminobenzenesulfonamide, as the active group in that reaction could be both the amine group of the sulfonamide moiety, as it was in the case of the reaction of benzene sulfonamide, or the aromatic amine group in the para position to the sulfonamide moiety, since the reactions of aromatic and aliphatic amines with carbimidates have been described [25, 26]. For that purpose, the reaction of methyl pyrazine-2-carbimidate with N-(4-sulfamoylphenyl)acetamide was carried out. The resulting product 9 was identical with the compound that was obtained by the acetic anhydride acylation of derivative 8, which was formed in the reaction of methyl pyrazine-2-carbimidate with 4-aminobenzenesulfonamide. This showed that the sulfonamide group was the active group in the reactions carried out, and the resulting compounds had structure c (Fig. 2).Fig. 2


Synthesis, structure, and antimicrobial activity of heterocyclic phenylsulfonyl- and 4-aminophenylsulfonyl-carboximidamides.

Gobis K, Foks H, Wiśniewska K, Dąbrowska-Szponar M, Augustynowicz-Kopeć E, Napiórkowska A, Sikorski A - Monatsh. Chem. (2012)

Structure of N′-(4-aminophenylsulfonyl)-4-chloropicolinimidamide showing 25 % probability displacements for ellipsoids. H atoms are shown as small spheres of arbitrary radius (intramolecular N–H···O and N–H···N interactions are represented by dashed lines)
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4494770&req=5

Fig2: Structure of N′-(4-aminophenylsulfonyl)-4-chloropicolinimidamide showing 25 % probability displacements for ellipsoids. H atoms are shown as small spheres of arbitrary radius (intramolecular N–H···O and N–H···N interactions are represented by dashed lines)
Mentions: The study also resolved the molecular structure of the products of the reaction between carbimidates and 4-aminobenzenesulfonamide, as the active group in that reaction could be both the amine group of the sulfonamide moiety, as it was in the case of the reaction of benzene sulfonamide, or the aromatic amine group in the para position to the sulfonamide moiety, since the reactions of aromatic and aliphatic amines with carbimidates have been described [25, 26]. For that purpose, the reaction of methyl pyrazine-2-carbimidate with N-(4-sulfamoylphenyl)acetamide was carried out. The resulting product 9 was identical with the compound that was obtained by the acetic anhydride acylation of derivative 8, which was formed in the reaction of methyl pyrazine-2-carbimidate with 4-aminobenzenesulfonamide. This showed that the sulfonamide group was the active group in the reactions carried out, and the resulting compounds had structure c (Fig. 2).Fig. 2

Bottom Line: A series of novel phenylsulfonyl- and 4-aminophenylsulfonyl-carboximidamides were synthesized by condensation of sulfonamides with heterocyclic methyl carbimidates obtained from heterocyclic carbonitriles and used 'at its inception.' The molecular structure of the obtained compounds is discussed.Compounds possessing heterocyclic systems with a nitrogen atom in the α position to the functional group showed a different single-crystal structure than expected.The synthesized derivatives were evaluated for antimicrobial activities: tuberculostatic, antibacterial, and antifungal. .

View Article: PubMed Central - PubMed

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

ABSTRACT

Abstract: A series of novel phenylsulfonyl- and 4-aminophenylsulfonyl-carboximidamides were synthesized by condensation of sulfonamides with heterocyclic methyl carbimidates obtained from heterocyclic carbonitriles and used 'at its inception.' The molecular structure of the obtained compounds is discussed. Compounds possessing heterocyclic systems with a nitrogen atom in the α position to the functional group showed a different single-crystal structure than expected. The synthesized derivatives were evaluated for antimicrobial activities: tuberculostatic, antibacterial, and antifungal.

Graphical abstract: .

No MeSH data available.


Related in: MedlinePlus