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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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Possible systems of intramolecular hydrogen bonds in target molecules
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Fig1: Possible systems of intramolecular hydrogen bonds in target molecules

Mentions: The structures of all these new compounds were confirmed by IR and NMR spectra as well as elemental analyses. Two signals for the NH groups shifted from each other have been observed in the 1H NMR spectra. These separated signals can be due to the taken amino-imine structure of compounds obtained (Fig. 1, structure a) as we suggest for 3- and 4-pyridine derivatives 3–6. They can also be a result of the magnetic inequivalence of NH protons in the amine moiety upon formation of a hydrogen bond in the case of the heterocyclic compounds in which the amidine group is in the α position to the nitrogen atom of heterocyclic ring (structure b). X-ray diffraction analysis was performed for N′-(4-aminophenylsulfonyl)-4-chloropicolinimidamide to address that question. We have described the synthesis of this compound previously [24]. It was chosen because we were able to obtain its crystals of sufficient size. The results of the single-crystal diffraction study confirmed a tautomeric structure b (Fig. 1). If both hydrogen atoms are bonded to the same nitrogen atom in the solid state, their magnetic inequivalence in the solution is probably caused by formation of hydrogen bonds and reduction of symmetry.Fig. 1


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)

Possible systems of intramolecular hydrogen bonds in target molecules
© Copyright Policy
Related In: Results  -  Collection

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

Fig1: Possible systems of intramolecular hydrogen bonds in target molecules
Mentions: The structures of all these new compounds were confirmed by IR and NMR spectra as well as elemental analyses. Two signals for the NH groups shifted from each other have been observed in the 1H NMR spectra. These separated signals can be due to the taken amino-imine structure of compounds obtained (Fig. 1, structure a) as we suggest for 3- and 4-pyridine derivatives 3–6. They can also be a result of the magnetic inequivalence of NH protons in the amine moiety upon formation of a hydrogen bond in the case of the heterocyclic compounds in which the amidine group is in the α position to the nitrogen atom of heterocyclic ring (structure b). X-ray diffraction analysis was performed for N′-(4-aminophenylsulfonyl)-4-chloropicolinimidamide to address that question. We have described the synthesis of this compound previously [24]. It was chosen because we were able to obtain its crystals of sufficient size. The results of the single-crystal diffraction study confirmed a tautomeric structure b (Fig. 1). If both hydrogen atoms are bonded to the same nitrogen atom in the solid state, their magnetic inequivalence in the solution is probably caused by formation of hydrogen bonds and reduction of symmetry.Fig. 1

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