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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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The  (20) hydrogen bond motif (a) and the arrangement of the molecules in the crystal structure of N′-(4-aminophenylsulfonyl)-4-chloropicolinimidamide viewed along b axis (b). Dashed lines: N–H···O and N–H···N interactions. H atoms not involved in interactions omitted
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Fig3: The (20) hydrogen bond motif (a) and the arrangement of the molecules in the crystal structure of N′-(4-aminophenylsulfonyl)-4-chloropicolinimidamide viewed along b axis (b). Dashed lines: N–H···O and N–H···N interactions. H atoms not involved in interactions omitted

Mentions: In the crystal structure of N′-(4-aminophenylsulfonyl)-4-chloropicolinimidamide, the H atoms from the amino group bonded with the C7 atom participate in the intramolecular N16–H16A···O18 and N16–H16B···N1 hydrogen bond (Table 3; Fig. 2). In the packing, the molecules are linked into chains of rings along the c axis (Fig. 3b). In these rings, four molecules of N′-(4-aminophenylsulfonyl)-4-chloropicolinimidamide are linked via N19–H19A···O17 and N19–H19B···N19 and form the (20) hydrogen bond ring motif (Fig. 3a). The parallel lying chains of rings are connected through the N16–H16A···O17 hydrogen bond and form columns along the b axis (Table 3; Fig. 3a). In the crystal lattice, these columns form a zipper-type supramolecular motif.Table 3


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)

The  (20) hydrogen bond motif (a) and the arrangement of the molecules in the crystal structure of N′-(4-aminophenylsulfonyl)-4-chloropicolinimidamide viewed along b axis (b). Dashed lines: N–H···O and N–H···N interactions. H atoms not involved in interactions omitted
© Copyright Policy
Related In: Results  -  Collection

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

Fig3: The (20) hydrogen bond motif (a) and the arrangement of the molecules in the crystal structure of N′-(4-aminophenylsulfonyl)-4-chloropicolinimidamide viewed along b axis (b). Dashed lines: N–H···O and N–H···N interactions. H atoms not involved in interactions omitted
Mentions: In the crystal structure of N′-(4-aminophenylsulfonyl)-4-chloropicolinimidamide, the H atoms from the amino group bonded with the C7 atom participate in the intramolecular N16–H16A···O18 and N16–H16B···N1 hydrogen bond (Table 3; Fig. 2). In the packing, the molecules are linked into chains of rings along the c axis (Fig. 3b). In these rings, four molecules of N′-(4-aminophenylsulfonyl)-4-chloropicolinimidamide are linked via N19–H19A···O17 and N19–H19B···N19 and form the (20) hydrogen bond ring motif (Fig. 3a). The parallel lying chains of rings are connected through the N16–H16A···O17 hydrogen bond and form columns along the b axis (Table 3; Fig. 3a). In the crystal lattice, these columns form a zipper-type supramolecular motif.Table 3

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