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Synthesis and biological activity of novel 3-heteroaryl-2H-pyrido[4,3-e][1,2,4]thiadiazine and 3-heteroaryl-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxides.

Gobis K, Foks H, Sławiński J, Augustynowicz-Kopeć E, Napiórkowska A - Monatsh. Chem. (2013)

Bottom Line: Those intermediates were successfully cyclized to corresponding 1,2,4-thiadiazine 1,1-dioxides in pyridine with the addition of DBU.The newly synthesized compounds were evaluated for their tuberculostatic and anticancer activities.Eight compounds were able to inhibit the growth of some renal and non-small cell lung cancer cell lines.

View Article: PubMed Central - PubMed

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

ABSTRACT

Abstract: A series of novel 1,2,4-thiadiazine 1,1-dioxides were synthesized by condensation of 2-chlorobenzenesulfonamide and 4-chloropyridine-3-sulfonamide with heterocyclic methyl carbimidates obtained from heterocyclic carbonitriles and used at the time of their creation. Substituted amidines were isolated as the intermediates in the reaction with 2-chlorobenzenesulfonamide. Those intermediates were successfully cyclized to corresponding 1,2,4-thiadiazine 1,1-dioxides in pyridine with the addition of DBU. The newly synthesized compounds were evaluated for their tuberculostatic and anticancer activities. Eight compounds were able to inhibit the growth of some renal and non-small cell lung cancer cell lines.

No MeSH data available.


Related in: MedlinePlus

Structures of possible tautomers of compound 6: 2H (6A) and 4H (6B)
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Fig1: Structures of possible tautomers of compound 6: 2H (6A) and 4H (6B)

Mentions: The 1H NMR signals for the aromatic protons and NH-group protons were observed at 12–13 ppm. To elucidate the possible tautomeric forms of the representative compounds 6 (Fig. 1) and 11, we estimated the total energies of the isolated molecules shown in Table 1.Fig. 1


Synthesis and biological activity of novel 3-heteroaryl-2H-pyrido[4,3-e][1,2,4]thiadiazine and 3-heteroaryl-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxides.

Gobis K, Foks H, Sławiński J, Augustynowicz-Kopeć E, Napiórkowska A - Monatsh. Chem. (2013)

Structures of possible tautomers of compound 6: 2H (6A) and 4H (6B)
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4495050&req=5

Fig1: Structures of possible tautomers of compound 6: 2H (6A) and 4H (6B)
Mentions: The 1H NMR signals for the aromatic protons and NH-group protons were observed at 12–13 ppm. To elucidate the possible tautomeric forms of the representative compounds 6 (Fig. 1) and 11, we estimated the total energies of the isolated molecules shown in Table 1.Fig. 1

Bottom Line: Those intermediates were successfully cyclized to corresponding 1,2,4-thiadiazine 1,1-dioxides in pyridine with the addition of DBU.The newly synthesized compounds were evaluated for their tuberculostatic and anticancer activities.Eight compounds were able to inhibit the growth of some renal and non-small cell lung cancer cell lines.

View Article: PubMed Central - PubMed

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

ABSTRACT

Abstract: A series of novel 1,2,4-thiadiazine 1,1-dioxides were synthesized by condensation of 2-chlorobenzenesulfonamide and 4-chloropyridine-3-sulfonamide with heterocyclic methyl carbimidates obtained from heterocyclic carbonitriles and used at the time of their creation. Substituted amidines were isolated as the intermediates in the reaction with 2-chlorobenzenesulfonamide. Those intermediates were successfully cyclized to corresponding 1,2,4-thiadiazine 1,1-dioxides in pyridine with the addition of DBU. The newly synthesized compounds were evaluated for their tuberculostatic and anticancer activities. Eight compounds were able to inhibit the growth of some renal and non-small cell lung cancer cell lines.

No MeSH data available.


Related in: MedlinePlus