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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.


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Mentions: One method presented in this article is to use 2-, 3-, and 4-pyridine-, 2-pyrimidine-, 2-pyrazine-, 6-chloro-2-pyrazine-, 6-methoxypyrazine-, and 2-quinolinecarbimidate. An important element of the chosen synthetic route is that there is no need for isolation of carbimidates and they are used in situ after generation from the corresponding carbonitriles in methanol in the presence of DBU (1,8-diazabicycloundec-7-ene). Isolated carbimidates are easy to obtain in pure form and can be also used for 2-pyrazine, 6-chloropyrazine, and 6-methoxypyrazine derivatives. The carbimidates mentioned above underwent reaction with 2-chlorobenzenesulfonamide and 4-chloropyridine-3-sulfonamide. The reactions were carried out in a methanol solution of DBU. That led to the formation of amidine structures with the 2-chlorobenzenesulfonyl or 4-chloropyridine-3-sulfonyl substituent (1–12, 15, 16; Scheme 1). The amidine structures 9, 10, 13, and 14 were prepared from pure isolated carbimidates by refluxing equimolar amounts of the reagents in diglyme (bis(2-methoxyethyl)ether).


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)

© Copyright Policy - OpenAccess
Related In: Results  -  Collection

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

Mentions: One method presented in this article is to use 2-, 3-, and 4-pyridine-, 2-pyrimidine-, 2-pyrazine-, 6-chloro-2-pyrazine-, 6-methoxypyrazine-, and 2-quinolinecarbimidate. An important element of the chosen synthetic route is that there is no need for isolation of carbimidates and they are used in situ after generation from the corresponding carbonitriles in methanol in the presence of DBU (1,8-diazabicycloundec-7-ene). Isolated carbimidates are easy to obtain in pure form and can be also used for 2-pyrazine, 6-chloropyrazine, and 6-methoxypyrazine derivatives. The carbimidates mentioned above underwent reaction with 2-chlorobenzenesulfonamide and 4-chloropyridine-3-sulfonamide. The reactions were carried out in a methanol solution of DBU. That led to the formation of amidine structures with the 2-chlorobenzenesulfonyl or 4-chloropyridine-3-sulfonyl substituent (1–12, 15, 16; Scheme 1). The amidine structures 9, 10, 13, and 14 were prepared from pure isolated carbimidates by refluxing equimolar amounts of the reagents in diglyme (bis(2-methoxyethyl)ether).

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