Synthesis, Characterization and Preliminary Study on Acetylpyrazine N(4)Butylthiosemicarbazone as a Potential CDK2 Inhibitor Combined with DFT Calculations
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Outros Autores: | , , |
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=S0103-50532018001002197 |
Resumo: | In this study, a new thiosemicarbazone ligand, namely acetylpyrazine N(4)butylthiosemicarbazone (APBT), was synthesized and characterized using 1H and 13C nuclear magnetic resonance (NMR) and Fourier transform infrared (FTIR) spectroscopies. Quantum chemical calculations were performed using density functional theory at the B3LYP/6-311++G(d,p) basis set level. The optimized molecular geometry of APBT is discussed based on X-ray structural reports from the literature. The assignment of the vibrational frequencies was done based on a potential energy distribution analysis using the vibrational energy distribution analysis (VEDA) 4 software. The energy gap between the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) was evaluated to study the reactivity and stability of the compound. Global chemical reactivity and local reactivity descriptors of reactants and the product (APBT) were calculated to study the reaction mechanism. The region of interaction during the reaction to form APBT was determined using molecular electrostatic potential analysis. Finally, a preliminary study of the title compound as a cyclin-dependent kinase (CDK) inhibitor was further evaluated by performing a docking calculation. |
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Synthesis, Characterization and Preliminary Study on Acetylpyrazine N(4)Butylthiosemicarbazone as a Potential CDK2 Inhibitor Combined with DFT CalculationsthiosemicarbazoneDFTglobal reactivity descriptorsCDK inhibitorIn this study, a new thiosemicarbazone ligand, namely acetylpyrazine N(4)butylthiosemicarbazone (APBT), was synthesized and characterized using 1H and 13C nuclear magnetic resonance (NMR) and Fourier transform infrared (FTIR) spectroscopies. Quantum chemical calculations were performed using density functional theory at the B3LYP/6-311++G(d,p) basis set level. The optimized molecular geometry of APBT is discussed based on X-ray structural reports from the literature. The assignment of the vibrational frequencies was done based on a potential energy distribution analysis using the vibrational energy distribution analysis (VEDA) 4 software. The energy gap between the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) was evaluated to study the reactivity and stability of the compound. Global chemical reactivity and local reactivity descriptors of reactants and the product (APBT) were calculated to study the reaction mechanism. The region of interaction during the reaction to form APBT was determined using molecular electrostatic potential analysis. Finally, a preliminary study of the title compound as a cyclin-dependent kinase (CDK) inhibitor was further evaluated by performing a docking calculation.Sociedade Brasileira de Química2018-10-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018001002197Journal of the Brazilian Chemical Society v.29 n.10 2018reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20180097info:eu-repo/semantics/openAccessNormaya,ErnaAhmad,Mohammad N.Farina,YangBulat,Ku H. K.eng2018-09-21T00:00:00Zoai:scielo:S0103-50532018001002197Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2018-09-21T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Synthesis, Characterization and Preliminary Study on Acetylpyrazine N(4)Butylthiosemicarbazone as a Potential CDK2 Inhibitor Combined with DFT Calculations |
title |
Synthesis, Characterization and Preliminary Study on Acetylpyrazine N(4)Butylthiosemicarbazone as a Potential CDK2 Inhibitor Combined with DFT Calculations |
spellingShingle |
Synthesis, Characterization and Preliminary Study on Acetylpyrazine N(4)Butylthiosemicarbazone as a Potential CDK2 Inhibitor Combined with DFT Calculations Normaya,Erna thiosemicarbazone DFT global reactivity descriptors CDK inhibitor |
title_short |
Synthesis, Characterization and Preliminary Study on Acetylpyrazine N(4)Butylthiosemicarbazone as a Potential CDK2 Inhibitor Combined with DFT Calculations |
title_full |
Synthesis, Characterization and Preliminary Study on Acetylpyrazine N(4)Butylthiosemicarbazone as a Potential CDK2 Inhibitor Combined with DFT Calculations |
title_fullStr |
Synthesis, Characterization and Preliminary Study on Acetylpyrazine N(4)Butylthiosemicarbazone as a Potential CDK2 Inhibitor Combined with DFT Calculations |
title_full_unstemmed |
Synthesis, Characterization and Preliminary Study on Acetylpyrazine N(4)Butylthiosemicarbazone as a Potential CDK2 Inhibitor Combined with DFT Calculations |
title_sort |
Synthesis, Characterization and Preliminary Study on Acetylpyrazine N(4)Butylthiosemicarbazone as a Potential CDK2 Inhibitor Combined with DFT Calculations |
author |
Normaya,Erna |
author_facet |
Normaya,Erna Ahmad,Mohammad N. Farina,Yang Bulat,Ku H. K. |
author_role |
author |
author2 |
Ahmad,Mohammad N. Farina,Yang Bulat,Ku H. K. |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
Normaya,Erna Ahmad,Mohammad N. Farina,Yang Bulat,Ku H. K. |
dc.subject.por.fl_str_mv |
thiosemicarbazone DFT global reactivity descriptors CDK inhibitor |
topic |
thiosemicarbazone DFT global reactivity descriptors CDK inhibitor |
description |
In this study, a new thiosemicarbazone ligand, namely acetylpyrazine N(4)butylthiosemicarbazone (APBT), was synthesized and characterized using 1H and 13C nuclear magnetic resonance (NMR) and Fourier transform infrared (FTIR) spectroscopies. Quantum chemical calculations were performed using density functional theory at the B3LYP/6-311++G(d,p) basis set level. The optimized molecular geometry of APBT is discussed based on X-ray structural reports from the literature. The assignment of the vibrational frequencies was done based on a potential energy distribution analysis using the vibrational energy distribution analysis (VEDA) 4 software. The energy gap between the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) was evaluated to study the reactivity and stability of the compound. Global chemical reactivity and local reactivity descriptors of reactants and the product (APBT) were calculated to study the reaction mechanism. The region of interaction during the reaction to form APBT was determined using molecular electrostatic potential analysis. Finally, a preliminary study of the title compound as a cyclin-dependent kinase (CDK) inhibitor was further evaluated by performing a docking calculation. |
publishDate |
2018 |
dc.date.none.fl_str_mv |
2018-10-01 |
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=S0103-50532018001002197 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018001002197 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.21577/0103-5053.20180097 |
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.29 n.10 2018 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_ |
1750318181232148480 |