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

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 wer...

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Autores principales: Gobis, Katarzyna, Foks, Henryk, Sławiński, Jarosłw, Augustynowicz-Kopeć, Ewa, Napiórkowska, Agnieszka
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2013
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4495050/
https://www.ncbi.nlm.nih.gov/pubmed/26166884
http://dx.doi.org/10.1007/s00706-013-0988-5
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author Gobis, Katarzyna
Foks, Henryk
Sławiński, Jarosłw
Augustynowicz-Kopeć, Ewa
Napiórkowska, Agnieszka
author_facet Gobis, Katarzyna
Foks, Henryk
Sławiński, Jarosłw
Augustynowicz-Kopeć, Ewa
Napiórkowska, Agnieszka
author_sort Gobis, Katarzyna
collection PubMed
description 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. GRAPHICAL ABSTRACT: [Image: see text]
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spelling pubmed-44950502015-07-09 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, Katarzyna Foks, Henryk Sławiński, Jarosłw Augustynowicz-Kopeć, Ewa Napiórkowska, Agnieszka Monatsh Chem Original Paper 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. GRAPHICAL ABSTRACT: [Image: see text] Springer Vienna 2013-05-14 2013 /pmc/articles/PMC4495050/ /pubmed/26166884 http://dx.doi.org/10.1007/s00706-013-0988-5 Text en © The Author(s) 2013 https://creativecommons.org/licenses/by/2.0/ Open AccessThis article is distributed under the terms of the Creative Commons Attribution License which permits any use, distribution, and reproduction in any medium, provided the original author(s) and the source are credited.
spellingShingle Original Paper
Gobis, Katarzyna
Foks, Henryk
Sławiński, Jarosłw
Augustynowicz-Kopeć, Ewa
Napiórkowska, Agnieszka
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Original Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4495050/
https://www.ncbi.nlm.nih.gov/pubmed/26166884
http://dx.doi.org/10.1007/s00706-013-0988-5
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