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Synthesis, Anticancer and Antitubercular Properties of New Chalcones and Their Nitrogen-Containing Five-Membered Heterocyclic Hybrids Bearing Sulfonamide Moiety

A new series of sulfonamides, 8a-b, 10, 12, and 14a-b, were synthesized by N-sulfonation reaction with sulfonyl chlorides 6a-b. Five new series of chalcone-sulfonamide hybrids (16-20)a-f were prepared via Claisen–Schmidt condensation of the newly obtained sulfonamides with aromatic aldehydes 15a-f i...

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Autores principales: Castaño, Lina Fernanda, Quiroga, Jairo, Abonia, Rodrigo, Insuasty, Daniel, Vidal, Oscar M., Seña, Rosalia, Rubio, Vivian, Puerto, Gloria, Nogueras, Manuel, Cobo, Justo, Guzman, Juan, Insuasty, Alberto, Insuasty, Braulio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9604400/
https://www.ncbi.nlm.nih.gov/pubmed/36293443
http://dx.doi.org/10.3390/ijms232012589
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author Castaño, Lina Fernanda
Quiroga, Jairo
Abonia, Rodrigo
Insuasty, Daniel
Vidal, Oscar M.
Seña, Rosalia
Rubio, Vivian
Puerto, Gloria
Nogueras, Manuel
Cobo, Justo
Guzman, Juan
Insuasty, Alberto
Insuasty, Braulio
author_facet Castaño, Lina Fernanda
Quiroga, Jairo
Abonia, Rodrigo
Insuasty, Daniel
Vidal, Oscar M.
Seña, Rosalia
Rubio, Vivian
Puerto, Gloria
Nogueras, Manuel
Cobo, Justo
Guzman, Juan
Insuasty, Alberto
Insuasty, Braulio
author_sort Castaño, Lina Fernanda
collection PubMed
description A new series of sulfonamides, 8a-b, 10, 12, and 14a-b, were synthesized by N-sulfonation reaction with sulfonyl chlorides 6a-b. Five new series of chalcone-sulfonamide hybrids (16-20)a-f were prepared via Claisen–Schmidt condensation of the newly obtained sulfonamides with aromatic aldehydes 15a-f in basic medium. Chalcones substituted with chlorine at position 4 of each series were used as precursors for the generation of their five-membered heterocyclic pyrazoline (22-23)a-d, (24-25)a-b and carbothioamide 27a-f derivatives. The synthesized compounds were evaluated for their anticancer and antituberculosis activities. To determine their anticancer activity, compounds were screened against sixty human cancer cell lines at a single dose (10 μM). Compounds 17a-c were highly active against LOX IMVI (melanoma), with IC(50) values of 0.34, 0.73 and 0.54 μM, respectively. Chalcone 18e showed remarkable results against the entire panel of leukemia cell lines with IC(50) values between 0.99–2.52 μM. Moreover, compounds 20e and 20f displayed growth inhibition of Mycobacterium tuberculosis H37Rv at concentrations below 10 μM. Although they showed low selectivity in cytotoxicity tests against the Vero cell line, further optimization could advance the potential biological activity of the selected compounds.
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spelling pubmed-96044002022-10-27 Synthesis, Anticancer and Antitubercular Properties of New Chalcones and Their Nitrogen-Containing Five-Membered Heterocyclic Hybrids Bearing Sulfonamide Moiety Castaño, Lina Fernanda Quiroga, Jairo Abonia, Rodrigo Insuasty, Daniel Vidal, Oscar M. Seña, Rosalia Rubio, Vivian Puerto, Gloria Nogueras, Manuel Cobo, Justo Guzman, Juan Insuasty, Alberto Insuasty, Braulio Int J Mol Sci Article A new series of sulfonamides, 8a-b, 10, 12, and 14a-b, were synthesized by N-sulfonation reaction with sulfonyl chlorides 6a-b. Five new series of chalcone-sulfonamide hybrids (16-20)a-f were prepared via Claisen–Schmidt condensation of the newly obtained sulfonamides with aromatic aldehydes 15a-f in basic medium. Chalcones substituted with chlorine at position 4 of each series were used as precursors for the generation of their five-membered heterocyclic pyrazoline (22-23)a-d, (24-25)a-b and carbothioamide 27a-f derivatives. The synthesized compounds were evaluated for their anticancer and antituberculosis activities. To determine their anticancer activity, compounds were screened against sixty human cancer cell lines at a single dose (10 μM). Compounds 17a-c were highly active against LOX IMVI (melanoma), with IC(50) values of 0.34, 0.73 and 0.54 μM, respectively. Chalcone 18e showed remarkable results against the entire panel of leukemia cell lines with IC(50) values between 0.99–2.52 μM. Moreover, compounds 20e and 20f displayed growth inhibition of Mycobacterium tuberculosis H37Rv at concentrations below 10 μM. Although they showed low selectivity in cytotoxicity tests against the Vero cell line, further optimization could advance the potential biological activity of the selected compounds. MDPI 2022-10-20 /pmc/articles/PMC9604400/ /pubmed/36293443 http://dx.doi.org/10.3390/ijms232012589 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Castaño, Lina Fernanda
Quiroga, Jairo
Abonia, Rodrigo
Insuasty, Daniel
Vidal, Oscar M.
Seña, Rosalia
Rubio, Vivian
Puerto, Gloria
Nogueras, Manuel
Cobo, Justo
Guzman, Juan
Insuasty, Alberto
Insuasty, Braulio
Synthesis, Anticancer and Antitubercular Properties of New Chalcones and Their Nitrogen-Containing Five-Membered Heterocyclic Hybrids Bearing Sulfonamide Moiety
title Synthesis, Anticancer and Antitubercular Properties of New Chalcones and Their Nitrogen-Containing Five-Membered Heterocyclic Hybrids Bearing Sulfonamide Moiety
title_full Synthesis, Anticancer and Antitubercular Properties of New Chalcones and Their Nitrogen-Containing Five-Membered Heterocyclic Hybrids Bearing Sulfonamide Moiety
title_fullStr Synthesis, Anticancer and Antitubercular Properties of New Chalcones and Their Nitrogen-Containing Five-Membered Heterocyclic Hybrids Bearing Sulfonamide Moiety
title_full_unstemmed Synthesis, Anticancer and Antitubercular Properties of New Chalcones and Their Nitrogen-Containing Five-Membered Heterocyclic Hybrids Bearing Sulfonamide Moiety
title_short Synthesis, Anticancer and Antitubercular Properties of New Chalcones and Their Nitrogen-Containing Five-Membered Heterocyclic Hybrids Bearing Sulfonamide Moiety
title_sort synthesis, anticancer and antitubercular properties of new chalcones and their nitrogen-containing five-membered heterocyclic hybrids bearing sulfonamide moiety
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9604400/
https://www.ncbi.nlm.nih.gov/pubmed/36293443
http://dx.doi.org/10.3390/ijms232012589
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