In silico-guided proposition of potential nematocidal and antibacterial N-(1,3,4-thiadiazol-2-yl)benzamides
Autor(a) principal: | |
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Data de Publicação: | 2022 |
Outros Autores: | , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UFLA |
Texto Completo: | http://repositorio.ufla.br/jspui/handle/1/50749 |
Resumo: | A series of amide derivatives containing the 1,3,4-thiadiazole moiety has been recently synthesized and tested against Meloidogyne incognita (Kofold & White) Chitwood (nematode) and Xanthomonas oryzae pv. oryzae (Ishiyama) Swings, van den Mooter, Vauterin, Hoste, Gillis, Mew & Kersters (rice bacteria). We have now reported the quantitative structure-activity relationship (QSAR) modeling of these biological activities, as well as docking studies to understand the action mechanisms of these compounds. Novel agrochemical candidates were proposed based on an interplay of the substituents which most affect the biological data. The reliable and predictive models obtained from multivariate image analysis applied to QSAR (nematocidal: r2 = 0.750 and r2pred = 0.751; antibacterial: r2 = 0.650 and r2pred = 0.668) were employed to estimate the biological activities of the proposed compounds. At least two chemical candidates for each endpoint exhibited promising agrochemical performance, as the substituents R1 = CF3 or 2,4-diCl, R2 = CH2CH2Cl or CH2CH2Br, and X = SO2 demonstrated a synergistic effect on the nematocidal and antibacterial activities. The promising outcomes were supported by docking studies against the acetylcholinesterase (for M. incognita) and β-ketoacyl-acyl carrier protein synthase (for Xoo) enzymes. |
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In silico-guided proposition of potential nematocidal and antibacterial N-(1,3,4-thiadiazol-2-yl)benzamidesQuantitative structure-activity relationship (QSAR)DockingMolecular modelingNematodeRice bacteriaRelações estrutura-atividade quantitativasModelagem molecularNematódeosXanthomonas oryzae pv. oryzaeA series of amide derivatives containing the 1,3,4-thiadiazole moiety has been recently synthesized and tested against Meloidogyne incognita (Kofold & White) Chitwood (nematode) and Xanthomonas oryzae pv. oryzae (Ishiyama) Swings, van den Mooter, Vauterin, Hoste, Gillis, Mew & Kersters (rice bacteria). We have now reported the quantitative structure-activity relationship (QSAR) modeling of these biological activities, as well as docking studies to understand the action mechanisms of these compounds. Novel agrochemical candidates were proposed based on an interplay of the substituents which most affect the biological data. The reliable and predictive models obtained from multivariate image analysis applied to QSAR (nematocidal: r2 = 0.750 and r2pred = 0.751; antibacterial: r2 = 0.650 and r2pred = 0.668) were employed to estimate the biological activities of the proposed compounds. At least two chemical candidates for each endpoint exhibited promising agrochemical performance, as the substituents R1 = CF3 or 2,4-diCl, R2 = CH2CH2Cl or CH2CH2Br, and X = SO2 demonstrated a synergistic effect on the nematocidal and antibacterial activities. The promising outcomes were supported by docking studies against the acetylcholinesterase (for M. incognita) and β-ketoacyl-acyl carrier protein synthase (for Xoo) enzymes.Elsevier2022-07-28T19:49:06Z2022-07-28T19:49:06Z2022-06info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfLICONA, J. S. F. et al. In silico-guided proposition of potential nematocidal and antibacterial N-(1,3,4-thiadiazol-2-yl)benzamides. Journal of Natural Pesticide Research, [S.I.], v. 1, 100003, June 2022. DOI: https://doi.org/10.1016/j.napere.2022.100003.http://repositorio.ufla.br/jspui/handle/1/50749Journal of Natural Pesticide Researchreponame:Repositório Institucional da UFLAinstname:Universidade Federal de Lavras (UFLA)instacron:UFLAhttp://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessLicona, Jessica S. F.Pereira, Ingrid V.Faria, Adriana C. deDaré, Joyce K.Cunha, Elaine F. F. daFreitas, Matheus P.eng2022-07-28T19:49:38Zoai:localhost:1/50749Repositório InstitucionalPUBhttp://repositorio.ufla.br/oai/requestnivaldo@ufla.br || repositorio.biblioteca@ufla.bropendoar:2022-07-28T19:49:38Repositório Institucional da UFLA - Universidade Federal de Lavras (UFLA)false |
dc.title.none.fl_str_mv |
In silico-guided proposition of potential nematocidal and antibacterial N-(1,3,4-thiadiazol-2-yl)benzamides |
title |
In silico-guided proposition of potential nematocidal and antibacterial N-(1,3,4-thiadiazol-2-yl)benzamides |
spellingShingle |
In silico-guided proposition of potential nematocidal and antibacterial N-(1,3,4-thiadiazol-2-yl)benzamides Licona, Jessica S. F. Quantitative structure-activity relationship (QSAR) Docking Molecular modeling Nematode Rice bacteria Relações estrutura-atividade quantitativas Modelagem molecular Nematódeos Xanthomonas oryzae pv. oryzae |
title_short |
In silico-guided proposition of potential nematocidal and antibacterial N-(1,3,4-thiadiazol-2-yl)benzamides |
title_full |
In silico-guided proposition of potential nematocidal and antibacterial N-(1,3,4-thiadiazol-2-yl)benzamides |
title_fullStr |
In silico-guided proposition of potential nematocidal and antibacterial N-(1,3,4-thiadiazol-2-yl)benzamides |
title_full_unstemmed |
In silico-guided proposition of potential nematocidal and antibacterial N-(1,3,4-thiadiazol-2-yl)benzamides |
title_sort |
In silico-guided proposition of potential nematocidal and antibacterial N-(1,3,4-thiadiazol-2-yl)benzamides |
author |
Licona, Jessica S. F. |
author_facet |
Licona, Jessica S. F. Pereira, Ingrid V. Faria, Adriana C. de Daré, Joyce K. Cunha, Elaine F. F. da Freitas, Matheus P. |
author_role |
author |
author2 |
Pereira, Ingrid V. Faria, Adriana C. de Daré, Joyce K. Cunha, Elaine F. F. da Freitas, Matheus P. |
author2_role |
author author author author author |
dc.contributor.author.fl_str_mv |
Licona, Jessica S. F. Pereira, Ingrid V. Faria, Adriana C. de Daré, Joyce K. Cunha, Elaine F. F. da Freitas, Matheus P. |
dc.subject.por.fl_str_mv |
Quantitative structure-activity relationship (QSAR) Docking Molecular modeling Nematode Rice bacteria Relações estrutura-atividade quantitativas Modelagem molecular Nematódeos Xanthomonas oryzae pv. oryzae |
topic |
Quantitative structure-activity relationship (QSAR) Docking Molecular modeling Nematode Rice bacteria Relações estrutura-atividade quantitativas Modelagem molecular Nematódeos Xanthomonas oryzae pv. oryzae |
description |
A series of amide derivatives containing the 1,3,4-thiadiazole moiety has been recently synthesized and tested against Meloidogyne incognita (Kofold & White) Chitwood (nematode) and Xanthomonas oryzae pv. oryzae (Ishiyama) Swings, van den Mooter, Vauterin, Hoste, Gillis, Mew & Kersters (rice bacteria). We have now reported the quantitative structure-activity relationship (QSAR) modeling of these biological activities, as well as docking studies to understand the action mechanisms of these compounds. Novel agrochemical candidates were proposed based on an interplay of the substituents which most affect the biological data. The reliable and predictive models obtained from multivariate image analysis applied to QSAR (nematocidal: r2 = 0.750 and r2pred = 0.751; antibacterial: r2 = 0.650 and r2pred = 0.668) were employed to estimate the biological activities of the proposed compounds. At least two chemical candidates for each endpoint exhibited promising agrochemical performance, as the substituents R1 = CF3 or 2,4-diCl, R2 = CH2CH2Cl or CH2CH2Br, and X = SO2 demonstrated a synergistic effect on the nematocidal and antibacterial activities. The promising outcomes were supported by docking studies against the acetylcholinesterase (for M. incognita) and β-ketoacyl-acyl carrier protein synthase (for Xoo) enzymes. |
publishDate |
2022 |
dc.date.none.fl_str_mv |
2022-07-28T19:49:06Z 2022-07-28T19:49:06Z 2022-06 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
LICONA, J. S. F. et al. In silico-guided proposition of potential nematocidal and antibacterial N-(1,3,4-thiadiazol-2-yl)benzamides. Journal of Natural Pesticide Research, [S.I.], v. 1, 100003, June 2022. DOI: https://doi.org/10.1016/j.napere.2022.100003. http://repositorio.ufla.br/jspui/handle/1/50749 |
identifier_str_mv |
LICONA, J. S. F. et al. In silico-guided proposition of potential nematocidal and antibacterial N-(1,3,4-thiadiazol-2-yl)benzamides. Journal of Natural Pesticide Research, [S.I.], v. 1, 100003, June 2022. DOI: https://doi.org/10.1016/j.napere.2022.100003. |
url |
http://repositorio.ufla.br/jspui/handle/1/50749 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.rights.driver.fl_str_mv |
http://creativecommons.org/licenses/by/4.0/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
http://creativecommons.org/licenses/by/4.0/ |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Elsevier |
publisher.none.fl_str_mv |
Elsevier |
dc.source.none.fl_str_mv |
Journal of Natural Pesticide Research reponame:Repositório Institucional da UFLA instname:Universidade Federal de Lavras (UFLA) instacron:UFLA |
instname_str |
Universidade Federal de Lavras (UFLA) |
instacron_str |
UFLA |
institution |
UFLA |
reponame_str |
Repositório Institucional da UFLA |
collection |
Repositório Institucional da UFLA |
repository.name.fl_str_mv |
Repositório Institucional da UFLA - Universidade Federal de Lavras (UFLA) |
repository.mail.fl_str_mv |
nivaldo@ufla.br || repositorio.biblioteca@ufla.br |
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1807835062280912896 |