Synthesis, in vitro Antimalarial Activity and in silico Studies of Hybrid Kauranoid 1,2,3-Triazoles Derived from Naturally Occurring Diterpenes

Synthesis, in vitro Antimalarial Activity and in silico Studies of Hybrid Kauranoid 1,2,3-Triazoles Derived from Naturally Occurring Diterpenes

We herein report the synthesis of hybrid kauranoid molecules of type 1,2,3-triazole-1,4-disubstituted aiming to improve the antimalarial activity of kaurenoic and xylopic acids. The CuI-catalyzed cycloaddition of azides and kauranoid terminal alkynes was explored as a hybridization strategy. Kauranoid terminal alkynes were prepared from kaurenoic and xylopic acids that were isolated from Wedelia paludosa D. C. (Asteraceae) and Xylopia frutescens Aubl. (Annonaceae). A total of 15 kauranoid derivatives, including nine new triazoles, were obtained and five out of these were more active than the original diterpenes. Interestingly, an increased activity was observed for a kauranoid propargyl ether. Interaction between ent-kaurane diterpene derivatives and Ca2+-ATPase (PfATP6) was investigated. Synthesis of diterpene derivatives emerges as a possible route to be explored in the quest of potentially new inhibitors of PfATP6.

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Main Authors: Santos,Juliana de O., Pereira,Guilherme R., Brandão,Geraldo C., Borgati,Tatiane F., Arantes,Lucas M., Paula,Renata C. de, Soares,Luciana F., Nascimento,Maria F. A. do, Ferreira,Márlia R. C., Taranto,Alex G., Varotti,Fernando P., Oliveira,Alaíde B. de
Format: Digital revista
Language:English
Published: Sociedade Brasileira de Química 2016
Online Access:http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000300551
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spelling oai:scielo:S0103-505320160003005512016-03-10Synthesis, in vitro Antimalarial Activity and in silico Studies of Hybrid Kauranoid 1,2,3-Triazoles Derived from Naturally Occurring DiterpenesSantos,Juliana de O.Pereira,Guilherme R.Brandão,Geraldo C.Borgati,Tatiane F.Arantes,Lucas M.Paula,Renata C. deSoares,Luciana F.Nascimento,Maria F. A. doFerreira,Márlia R. C.Taranto,Alex G.Varotti,Fernando P.Oliveira,Alaíde B. de kaurenoic acid xylopic acid click chemistry antiplasmodial activity PfATP6 inhibitors We herein report the synthesis of hybrid kauranoid molecules of type 1,2,3-triazole-1,4-disubstituted aiming to improve the antimalarial activity of kaurenoic and xylopic acids. The CuI-catalyzed cycloaddition of azides and kauranoid terminal alkynes was explored as a hybridization strategy. Kauranoid terminal alkynes were prepared from kaurenoic and xylopic acids that were isolated from Wedelia paludosa D. C. (Asteraceae) and Xylopia frutescens Aubl. (Annonaceae). A total of 15 kauranoid derivatives, including nine new triazoles, were obtained and five out of these were more active than the original diterpenes. Interestingly, an increased activity was observed for a kauranoid propargyl ether. Interaction between ent-kaurane diterpene derivatives and Ca2+-ATPase (PfATP6) was investigated. Synthesis of diterpene derivatives emerges as a possible route to be explored in the quest of potentially new inhibitors of PfATP6.info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.27 n.3 20162016-03-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000300551en10.5935/0103-5053.20150287
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language English
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author Santos,Juliana de O.
Pereira,Guilherme R.
Brandão,Geraldo C.
Borgati,Tatiane F.
Arantes,Lucas M.
Paula,Renata C. de
Soares,Luciana F.
Nascimento,Maria F. A. do
Ferreira,Márlia R. C.
Taranto,Alex G.
Varotti,Fernando P.
Oliveira,Alaíde B. de
spellingShingle Santos,Juliana de O.
Pereira,Guilherme R.
Brandão,Geraldo C.
Borgati,Tatiane F.
Arantes,Lucas M.
Paula,Renata C. de
Soares,Luciana F.
Nascimento,Maria F. A. do
Ferreira,Márlia R. C.
Taranto,Alex G.
Varotti,Fernando P.
Oliveira,Alaíde B. de
Synthesis, in vitro Antimalarial Activity and in silico Studies of Hybrid Kauranoid 1,2,3-Triazoles Derived from Naturally Occurring Diterpenes
author_facet Santos,Juliana de O.
Pereira,Guilherme R.
Brandão,Geraldo C.
Borgati,Tatiane F.
Arantes,Lucas M.
Paula,Renata C. de
Soares,Luciana F.
Nascimento,Maria F. A. do
Ferreira,Márlia R. C.
Taranto,Alex G.
Varotti,Fernando P.
Oliveira,Alaíde B. de
author_sort Santos,Juliana de O.
title Synthesis, in vitro Antimalarial Activity and in silico Studies of Hybrid Kauranoid 1,2,3-Triazoles Derived from Naturally Occurring Diterpenes
title_short Synthesis, in vitro Antimalarial Activity and in silico Studies of Hybrid Kauranoid 1,2,3-Triazoles Derived from Naturally Occurring Diterpenes
title_full Synthesis, in vitro Antimalarial Activity and in silico Studies of Hybrid Kauranoid 1,2,3-Triazoles Derived from Naturally Occurring Diterpenes
title_fullStr Synthesis, in vitro Antimalarial Activity and in silico Studies of Hybrid Kauranoid 1,2,3-Triazoles Derived from Naturally Occurring Diterpenes
title_full_unstemmed Synthesis, in vitro Antimalarial Activity and in silico Studies of Hybrid Kauranoid 1,2,3-Triazoles Derived from Naturally Occurring Diterpenes
title_sort synthesis, in vitro antimalarial activity and in silico studies of hybrid kauranoid 1,2,3-triazoles derived from naturally occurring diterpenes
description We herein report the synthesis of hybrid kauranoid molecules of type 1,2,3-triazole-1,4-disubstituted aiming to improve the antimalarial activity of kaurenoic and xylopic acids. The CuI-catalyzed cycloaddition of azides and kauranoid terminal alkynes was explored as a hybridization strategy. Kauranoid terminal alkynes were prepared from kaurenoic and xylopic acids that were isolated from Wedelia paludosa D. C. (Asteraceae) and Xylopia frutescens Aubl. (Annonaceae). A total of 15 kauranoid derivatives, including nine new triazoles, were obtained and five out of these were more active than the original diterpenes. Interestingly, an increased activity was observed for a kauranoid propargyl ether. Interaction between ent-kaurane diterpene derivatives and Ca2+-ATPase (PfATP6) was investigated. Synthesis of diterpene derivatives emerges as a possible route to be explored in the quest of potentially new inhibitors of PfATP6.
publisher Sociedade Brasileira de Química
publishDate 2016
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000300551
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