Synthesis, in silico Study and Antileishmanial Evaluation of New Selenides Derived from 7-Chloro-quinoline and N-Phenylacetamides
This study describes a virtual screening performed for two series of selenides (28 compounds), derived from N-phenylacetamides chlorides and 7-chloro-quinoline, to determine their potential for leishmanicidal activity against Leishmania amazonensis and Leishmania donovani. Seven compounds were predicted as potential leishmanicides; therefore, they were synthesized from elemental selenium, as a precursor for the production of NaHSe, and subsequent reactions with 4,7-dichloro-quinoline and N-phenylacetamides chlorides were performed. The compounds were characterized by infrared (IR), 1H and 13C nuclear magnetic resonance (NMR), and sent for in vitro cytotoxicity tests against L. amazonensis and were found to be active and selective, and two compounds presented half-maximal inhibitory concentrations (IC50) of 5.67 and 10.81 µg mL-1. They also presented good interaction energies in the docking study, suggesting that may exert their effects by inhibiting the N-myristoyltransferase and O-acetylserine sulfhydrylase enzymes in parasites.
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Sociedade Brasileira de Química
2021
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oai:scielo:S0103-505320210004007122021-03-25Synthesis, in silico Study and Antileishmanial Evaluation of New Selenides Derived from 7-Chloro-quinoline and N-PhenylacetamidesHuang,Min-Fu N.Luis,José A. S.Silva,Alison P. daRocha,Juliana C.Lima,Tatjana K. S.Scotti,Marcus T.Scotti,LucianaOliveira,Rafael F. deSouza,Helivaldo D. S.Athayde-Filho,Petrônio F. deBarbosa-Filho,José M. selenium selenide virtual screening anti-leishmanial molecular docking This study describes a virtual screening performed for two series of selenides (28 compounds), derived from N-phenylacetamides chlorides and 7-chloro-quinoline, to determine their potential for leishmanicidal activity against Leishmania amazonensis and Leishmania donovani. Seven compounds were predicted as potential leishmanicides; therefore, they were synthesized from elemental selenium, as a precursor for the production of NaHSe, and subsequent reactions with 4,7-dichloro-quinoline and N-phenylacetamides chlorides were performed. The compounds were characterized by infrared (IR), 1H and 13C nuclear magnetic resonance (NMR), and sent for in vitro cytotoxicity tests against L. amazonensis and were found to be active and selective, and two compounds presented half-maximal inhibitory concentrations (IC50) of 5.67 and 10.81 µg mL-1. They also presented good interaction energies in the docking study, suggesting that may exert their effects by inhibiting the N-myristoyltransferase and O-acetylserine sulfhydrylase enzymes in parasites.info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.32 n.4 20212021-04-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000400712en10.21577/0103-5053.20200223 |
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Huang,Min-Fu N. Luis,José A. S. Silva,Alison P. da Rocha,Juliana C. Lima,Tatjana K. S. Scotti,Marcus T. Scotti,Luciana Oliveira,Rafael F. de Souza,Helivaldo D. S. Athayde-Filho,Petrônio F. de Barbosa-Filho,José M. |
spellingShingle |
Huang,Min-Fu N. Luis,José A. S. Silva,Alison P. da Rocha,Juliana C. Lima,Tatjana K. S. Scotti,Marcus T. Scotti,Luciana Oliveira,Rafael F. de Souza,Helivaldo D. S. Athayde-Filho,Petrônio F. de Barbosa-Filho,José M. Synthesis, in silico Study and Antileishmanial Evaluation of New Selenides Derived from 7-Chloro-quinoline and N-Phenylacetamides |
author_facet |
Huang,Min-Fu N. Luis,José A. S. Silva,Alison P. da Rocha,Juliana C. Lima,Tatjana K. S. Scotti,Marcus T. Scotti,Luciana Oliveira,Rafael F. de Souza,Helivaldo D. S. Athayde-Filho,Petrônio F. de Barbosa-Filho,José M. |
author_sort |
Huang,Min-Fu N. |
title |
Synthesis, in silico Study and Antileishmanial Evaluation of New Selenides Derived from 7-Chloro-quinoline and N-Phenylacetamides |
title_short |
Synthesis, in silico Study and Antileishmanial Evaluation of New Selenides Derived from 7-Chloro-quinoline and N-Phenylacetamides |
title_full |
Synthesis, in silico Study and Antileishmanial Evaluation of New Selenides Derived from 7-Chloro-quinoline and N-Phenylacetamides |
title_fullStr |
Synthesis, in silico Study and Antileishmanial Evaluation of New Selenides Derived from 7-Chloro-quinoline and N-Phenylacetamides |
title_full_unstemmed |
Synthesis, in silico Study and Antileishmanial Evaluation of New Selenides Derived from 7-Chloro-quinoline and N-Phenylacetamides |
title_sort |
synthesis, in silico study and antileishmanial evaluation of new selenides derived from 7-chloro-quinoline and n-phenylacetamides |
description |
This study describes a virtual screening performed for two series of selenides (28 compounds), derived from N-phenylacetamides chlorides and 7-chloro-quinoline, to determine their potential for leishmanicidal activity against Leishmania amazonensis and Leishmania donovani. Seven compounds were predicted as potential leishmanicides; therefore, they were synthesized from elemental selenium, as a precursor for the production of NaHSe, and subsequent reactions with 4,7-dichloro-quinoline and N-phenylacetamides chlorides were performed. The compounds were characterized by infrared (IR), 1H and 13C nuclear magnetic resonance (NMR), and sent for in vitro cytotoxicity tests against L. amazonensis and were found to be active and selective, and two compounds presented half-maximal inhibitory concentrations (IC50) of 5.67 and 10.81 µg mL-1. They also presented good interaction energies in the docking study, suggesting that may exert their effects by inhibiting the N-myristoyltransferase and O-acetylserine sulfhydrylase enzymes in parasites. |
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Sociedade Brasileira de Química |
publishDate |
2021 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000400712 |
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