Please use this identifier to cite or link to this item:
https://hdl.handle.net/10316/100846
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Chaves, Otávio Augusto | - |
dc.contributor.author | Sueth-Santiago, Vitor | - |
dc.contributor.author | Pinto, Douglas Chaves de Alcântara | - |
dc.contributor.author | Netto-Ferreira, José Carlos | - |
dc.contributor.author | Decote-Ricardo, Debora | - |
dc.contributor.author | Lima, Marco Edilson Freire de | - |
dc.date.accessioned | 2022-07-14T10:43:37Z | - |
dc.date.available | 2022-07-14T10:43:37Z | - |
dc.date.issued | 2021 | - |
dc.identifier.issn | 1422-8599 | pt |
dc.identifier.uri | https://hdl.handle.net/10316/100846 | - |
dc.description.abstract | A novel curcumin analog namely 2-chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]- styryl}pyrimidine (compound 7) was synthesized by three-step reaction. The condensation reaction of protected vanillin with 2-chloro-4,6-dimethylpyrimidine (6) was the most efficient step, resulting in a total yield of 72%. The characterization of compound 7was performed by 1Hand 13C nuclearmagnetic resonance (NMR), as well as high-resolution mass spectrometry. The experimental spectrometric data were compared with the theoretical spectra obtained by the density functional theory (DFT) method, showing a perfectmatch between them.UV-visible spectroscopy and steady-state fluorescence emission studies were performed for compound 7 in solvents of different polarities and the results were correlated with DFT calculations. Compound 7 showed a solvatochromism effect presenting higher molar extinction coefficient (log " = 4.57) and fluorescence quantum yield ( = 0.38) in toluene than in acetonitrile or methanol. The simulation of both frontier molecular orbitals (FMOs) and molecular electrostatic potential (MEP) suggested that the experimental spectra profile in toluene was not interfered by a possible charge transfer. These results are an indication of a low probability of compound 7 in reacting with unsaturated phospholipids in future applications as a fluorescent dye in biological systems. | pt |
dc.description.sponsorship | This research was funded by the Brazilian agencies: Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and Fundação Carlos Chagas Filho de Amparo à Pesquisa do Estado do Rio de Janeiro (FAPERJ). The funders had no role in the design of the study; in the collection, analyses or interpretation of data; in the writing of the manuscript or in the decision to publish the results. | pt |
dc.language.iso | eng | pt |
dc.rights | openAccess | pt |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | pt |
dc.subject | curcumin analog | pt |
dc.subject | organic synthesis | pt |
dc.subject | photophysical properties | pt |
dc.subject | steady-state fluorescence | pt |
dc.subject | DFT calculation | pt |
dc.title | 2-Chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]styryl}pyrimidine: Synthesis, Spectroscopic and Computational Evaluation | pt |
dc.type | article | - |
degois.publication.firstPage | M1276 | pt |
degois.publication.issue | 3 | pt |
degois.publication.title | MolBank | pt |
dc.peerreviewed | yes | pt |
dc.identifier.doi | 10.3390/M1276 | pt |
degois.publication.volume | 2021 | pt |
dc.date.embargo | 2021-01-01 | * |
uc.date.periodoEmbargo | 0 | pt |
item.fulltext | Com Texto completo | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
item.languageiso639-1 | en | - |
item.openairetype | article | - |
item.cerifentitytype | Publications | - |
item.grantfulltext | open | - |
crisitem.author.researchunit | CQC - Coimbra Chemistry Centre | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.orcid | 0000-0001-6211-7659 | - |
Appears in Collections: | I&D CQC - Artigos em Revistas Internacionais |
Files in This Item:
File | Description | Size | Format | |
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2chloro46bisE3methoxy44methoxybenzyloxystyrylpyrimidine-Synthesis-spectroscopic-and-computational-evaluationMolBank.pdf | 1.58 MB | Adobe PDF | View/Open |
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This item is licensed under a Creative Commons License