Synthesis, in vitro Antiproliferative and Anti-Mycobacterium tuberculosis Activities of Novel β-Carboline Derivatives

Detalhes bibliográficos
Autor(a) principal: Moreira,Flora M. F.
Data de Publicação: 2016
Outros Autores: Croda,Julio, Sarragiotto,Maria H., Foglio,Mary A., Ruiz,Ana L. T. G., Carvalho,João E., Formagio,Anelise S. N.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000801398
Resumo: A series of β-carboline derivatives with amino or guanidinium were synthesized and evaluated in vitro against anti-Mycobacterium tuberculosis and for antiproliferative activities against nine human cancer cell lines. The compounds 1-(4-hydroxyphenyl)-3-carboxamide(ethylamine) β-carboline (24.9 µg mL-1) and 1-(4-methoxyphenyl)-3-carboxamide(ethylamine) β-carboline (26.9 µg mL-1) were the most active against M. Tuberculosis (MTB). Compounds 1-(4-hydroxyphenyl)-3-carboxamide(ethylamine) β-carboline and 1-(4-methoxyphenyl)-3-carboxamide(propylamine) β-carboline, which had the same substituted groups, inhibited the growth of all human tumor cell lines with growth inhibitory activity (GI50) values from 1.37 to 9.20 mmol L-1. Also in this series, compounds 1-(4-hydroxyphenyl)-3-carboxamide(propylamine) β-carboline and 1-(3-nitrophenyl)-3-carboxamide(propylamine) β-carboline demonstrated significant activity against NCI/ADR cells. Among compounds with a terminal guanidine group, compounds 1-(4-hydroxyphenyl)-3-carboxamide(ethyl)guanidine β-carboline (27.8 µg mL-1) and 1-(3-nitrophenyl)-3-carboxamide(ethyl)guanidine β-carboline (37.4 µg mL-1) demonstrated the greatest activity against MTB. Additionally, compounds 1-(4-methoxyphenyl)-3-carboxamide(ethyl)guanidine β-carboline (GI50 = 0.45 mmol L-1) effectively inhibited growth and was highly selective against NCI/ADR. The in silico study revealed that 1-(4-hydroxyphenyl)-3-carboxamide(ethylamine) β-carboline, 1-(4-methoxyphenyl)-3-carboxamide(ethylamine) β-carboline, 1-(4-hydroxyphenyl)-3-carboxamide(propylamine) β-carboline, 1-(4-methoxyphenyl)-3-carboxamide(propylamine) β-carboline and 1-(3-nitrophenyl)-3-carboxamide(propylamine) β-carboline compounds follow the rules established by Lipinski, suggesting that this compound has no problems with oral bioavailability.
id SBQ-2_120bb620b3bd9af0b0b08f63bee75f60
oai_identifier_str oai:scielo:S0103-50532016000801398
network_acronym_str SBQ-2
network_name_str Journal of the Brazilian Chemical Society (Online)
repository_id_str
spelling Synthesis, in vitro Antiproliferative and Anti-Mycobacterium tuberculosis Activities of Novel β-Carboline Derivativessynthesisβ-carbolineMycobacterium tuberculosisantiproliferative activityA series of β-carboline derivatives with amino or guanidinium were synthesized and evaluated in vitro against anti-Mycobacterium tuberculosis and for antiproliferative activities against nine human cancer cell lines. The compounds 1-(4-hydroxyphenyl)-3-carboxamide(ethylamine) β-carboline (24.9 µg mL-1) and 1-(4-methoxyphenyl)-3-carboxamide(ethylamine) β-carboline (26.9 µg mL-1) were the most active against M. Tuberculosis (MTB). Compounds 1-(4-hydroxyphenyl)-3-carboxamide(ethylamine) β-carboline and 1-(4-methoxyphenyl)-3-carboxamide(propylamine) β-carboline, which had the same substituted groups, inhibited the growth of all human tumor cell lines with growth inhibitory activity (GI50) values from 1.37 to 9.20 mmol L-1. Also in this series, compounds 1-(4-hydroxyphenyl)-3-carboxamide(propylamine) β-carboline and 1-(3-nitrophenyl)-3-carboxamide(propylamine) β-carboline demonstrated significant activity against NCI/ADR cells. Among compounds with a terminal guanidine group, compounds 1-(4-hydroxyphenyl)-3-carboxamide(ethyl)guanidine β-carboline (27.8 µg mL-1) and 1-(3-nitrophenyl)-3-carboxamide(ethyl)guanidine β-carboline (37.4 µg mL-1) demonstrated the greatest activity against MTB. Additionally, compounds 1-(4-methoxyphenyl)-3-carboxamide(ethyl)guanidine β-carboline (GI50 = 0.45 mmol L-1) effectively inhibited growth and was highly selective against NCI/ADR. The in silico study revealed that 1-(4-hydroxyphenyl)-3-carboxamide(ethylamine) β-carboline, 1-(4-methoxyphenyl)-3-carboxamide(ethylamine) β-carboline, 1-(4-hydroxyphenyl)-3-carboxamide(propylamine) β-carboline, 1-(4-methoxyphenyl)-3-carboxamide(propylamine) β-carboline and 1-(3-nitrophenyl)-3-carboxamide(propylamine) β-carboline compounds follow the rules established by Lipinski, suggesting that this compound has no problems with oral bioavailability.Sociedade Brasileira de Química2016-08-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000801398Journal of the Brazilian Chemical Society v.27 n.8 2016reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20160062info:eu-repo/semantics/openAccessMoreira,Flora M. F.Croda,JulioSarragiotto,Maria H.Foglio,Mary A.Ruiz,Ana L. T. G.Carvalho,João E.Formagio,Anelise S. N.eng2016-08-19T00:00:00Zoai:scielo:S0103-50532016000801398Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2016-08-19T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis, in vitro Antiproliferative and Anti-Mycobacterium tuberculosis Activities of Novel β-Carboline Derivatives
title Synthesis, in vitro Antiproliferative and Anti-Mycobacterium tuberculosis Activities of Novel β-Carboline Derivatives
spellingShingle Synthesis, in vitro Antiproliferative and Anti-Mycobacterium tuberculosis Activities of Novel β-Carboline Derivatives
Moreira,Flora M. F.
synthesis
β-carboline
Mycobacterium tuberculosis
antiproliferative activity
title_short Synthesis, in vitro Antiproliferative and Anti-Mycobacterium tuberculosis Activities of Novel β-Carboline Derivatives
title_full Synthesis, in vitro Antiproliferative and Anti-Mycobacterium tuberculosis Activities of Novel β-Carboline Derivatives
title_fullStr Synthesis, in vitro Antiproliferative and Anti-Mycobacterium tuberculosis Activities of Novel β-Carboline Derivatives
title_full_unstemmed Synthesis, in vitro Antiproliferative and Anti-Mycobacterium tuberculosis Activities of Novel β-Carboline Derivatives
title_sort Synthesis, in vitro Antiproliferative and Anti-Mycobacterium tuberculosis Activities of Novel β-Carboline Derivatives
author Moreira,Flora M. F.
author_facet Moreira,Flora M. F.
Croda,Julio
Sarragiotto,Maria H.
Foglio,Mary A.
Ruiz,Ana L. T. G.
Carvalho,João E.
Formagio,Anelise S. N.
author_role author
author2 Croda,Julio
Sarragiotto,Maria H.
Foglio,Mary A.
Ruiz,Ana L. T. G.
Carvalho,João E.
Formagio,Anelise S. N.
author2_role author
author
author
author
author
author
dc.contributor.author.fl_str_mv Moreira,Flora M. F.
Croda,Julio
Sarragiotto,Maria H.
Foglio,Mary A.
Ruiz,Ana L. T. G.
Carvalho,João E.
Formagio,Anelise S. N.
dc.subject.por.fl_str_mv synthesis
β-carboline
Mycobacterium tuberculosis
antiproliferative activity
topic synthesis
β-carboline
Mycobacterium tuberculosis
antiproliferative activity
description A series of β-carboline derivatives with amino or guanidinium were synthesized and evaluated in vitro against anti-Mycobacterium tuberculosis and for antiproliferative activities against nine human cancer cell lines. The compounds 1-(4-hydroxyphenyl)-3-carboxamide(ethylamine) β-carboline (24.9 µg mL-1) and 1-(4-methoxyphenyl)-3-carboxamide(ethylamine) β-carboline (26.9 µg mL-1) were the most active against M. Tuberculosis (MTB). Compounds 1-(4-hydroxyphenyl)-3-carboxamide(ethylamine) β-carboline and 1-(4-methoxyphenyl)-3-carboxamide(propylamine) β-carboline, which had the same substituted groups, inhibited the growth of all human tumor cell lines with growth inhibitory activity (GI50) values from 1.37 to 9.20 mmol L-1. Also in this series, compounds 1-(4-hydroxyphenyl)-3-carboxamide(propylamine) β-carboline and 1-(3-nitrophenyl)-3-carboxamide(propylamine) β-carboline demonstrated significant activity against NCI/ADR cells. Among compounds with a terminal guanidine group, compounds 1-(4-hydroxyphenyl)-3-carboxamide(ethyl)guanidine β-carboline (27.8 µg mL-1) and 1-(3-nitrophenyl)-3-carboxamide(ethyl)guanidine β-carboline (37.4 µg mL-1) demonstrated the greatest activity against MTB. Additionally, compounds 1-(4-methoxyphenyl)-3-carboxamide(ethyl)guanidine β-carboline (GI50 = 0.45 mmol L-1) effectively inhibited growth and was highly selective against NCI/ADR. The in silico study revealed that 1-(4-hydroxyphenyl)-3-carboxamide(ethylamine) β-carboline, 1-(4-methoxyphenyl)-3-carboxamide(ethylamine) β-carboline, 1-(4-hydroxyphenyl)-3-carboxamide(propylamine) β-carboline, 1-(4-methoxyphenyl)-3-carboxamide(propylamine) β-carboline and 1-(3-nitrophenyl)-3-carboxamide(propylamine) β-carboline compounds follow the rules established by Lipinski, suggesting that this compound has no problems with oral bioavailability.
publishDate 2016
dc.date.none.fl_str_mv 2016-08-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000801398
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000801398
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.5935/0103-5053.20160062
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.27 n.8 2016
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
_version_ 1750318178680963072