Navegando por Autor "Duarte, Vitor Santos"
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- ItemArylsulfonamide chalcones as alternatives for fuel additives: antioxidant activity and machine learning protocol studies(2023) Duarte, Vitor Santos; Borges, Igor Dalarmelino; D´Oliveira, Giulio Demetrius Creazzo; Faria, Eduardo Coelho da Mata; Almeida, Leonardo Rodrigues de; Silva, Valter Henrique Carvalho; Noda Pérez, Caridad; Napolitano, Hamilton BarbosaBiodiesel is a promising fuel with the potential to reduce some negative aspects of fossil fuels, such as the emission of pollutants and greenhouse gases (GHGs), the scarcity of natural resources and market instability. To amplify its low durability and stability the use of technologies based on molecular compounds that reduce the oxidation rate of biodiesel and preserve its physical–chemical properties is very common and necessary throughout the world. To reduce oxidative stability problems of diesel–biodiesel blends, arylsulfonamide chalcones were evaluated as potential additives for B20 blends. In this study, comprehensive structural, computational, and experimental analyses were undertaken to understand the antioxidant potential of these compounds as possible additives. The supramolecular arrangements were stabilized by weak molecular interactions (C–H⋯O and C–H⋯π), which are related to antioxidant and antibacterial action, and groups can act as electron-donating substituents. The energy range of 593.1–570.2 kJ mol−1 in the frontier molecular orbitals indicates high structural stability, due particularly to sulfonamide groups which enable electrophilic attack. Furthermore, the Fukui function aligned with kinetics parameters, obtained using machine learning protocols, provided information to clarify and expand the comprehension of chalcone antioxidant features mediated by free-radical capture. The heat of combustion indicated good energy availability (6530.5–7306.5 kcal kg−1), close to those of conventional fuels. In addition, the oxidative stability of the diesel–biodiesel blend (B20) remained at around 27 hours, after 140 days of storage, which is better than for some commercial additives. We hope that this comprehensive study will support the understanding of chalcone-based compounds as alternatives to fuel additives.
- ItemA comparative structural analysis of arylsulfonamide chalcones with potential as a biofuel additive(2023) Vieira, Diego Freire; Borges, Igor Dalarmelino; Aguiar, Antônio Sérgio Nakao de; Duarte, Vitor Santos; D´Oliveira, Giulio Demetrius Creazzo; Vaz, Wesley Fonseca; Costa, Rogério Ferreira da; Noda Pérez, Caridad; Napolitano, Hamilton BarbosaBiodiesel has a significant added value compared to petrodiesel regarding a series of improved properties such as biodegradability and reduction of most regulated exhaust emissions. However, some challenges associated with biodiesel include physicochemical improvements in oxidative stability, which can be addressed by antioxidants. In this aspect, chalcone derivatives are simple chemical scaffolds with industrial applications that can be boosted by the insertion of a sulfonamide group. An extensive structure characterization was carried out for arylsulfonamide chalcone N-(2-(3–4-methoxyphenyl-propanoyl)-phenyl)-benzenesulfonamide and its isomer, to describe their supramolecular arrangements and conformational changes. Solid state arrangements were described by XRD and stabilized by C–H⋯O and π⋯π stacking interactions. Theoretical calculations were carried out by DFT using the M06-2X/6-311++G(d,p) level of theory to identify the reactive sites of arylsulfonamide chalcones and their molecular electrostatic potential maps. The fundamental factors were correlated to antioxidant molecules and commercial additives found in the literature. The analysis carried out in this work will be a gateway to confirm the relationship between the structure of arylsulfonamide chalcones and their additive properties as biofuels.
- ItemExperimental and molecular modeling study of a novel arylsulfonamide chalcone(2019) Duarte, Vitor Santos; D´Oliveira, Giulio Demetrius Creazzo; Custodio, Jean Marcos Ferreira; Oliveira, Solemar Silva; Noda Pérez, Caridad; Napolitano, Hamilton BarbosaChalcones have been reported to present biological activities that are potentialized when a sulfonamide group is attached. A comprehensive structural study was performed for arylsulfonamide chalcone N-(2-(3–4-methoxyphenyl-propanoyl)-phenyl)-benzene-sulfonamide in order to describe its supramolecular arrangement and its physicochemical properties. The molecular packing arrangement was described by X-ray diffraction and Hirshfeld surfaces (HS). Theoretical calculations were performed using density functional theory (DFT), molecular electrostatic potential (MEP) mapping, ab initio Car-Parrinelo molecular dynamics (CPMD) and the quantum theory of atoms in molecules (QTAIM). The solid-state arrangement is stabilized by C– H⋯O and C–H⋯π interactions observed on HS and MEP map. The topological analysis was evaluated by QTAIM.
- ItemInsights into chalcone analogues with potential as antioxidant additives in diesel–biodiesel blends(2022) Borges, Igor Dalarmelino; Faria, Eduardo Coelho da Mata; Custodio, Jean Marcos Ferreira; Duarte, Vitor Santos; Fernandes, Fernanda de Sousa; Alonso, Christian Gonçalves; Silva, Valter Henrique Carvalho; Oliveira, Guilherme Roberto de; Napolitano, Hamilton BarbosaBiodiesel production is one of the promising strategies to reduce diesel consumption and an important contribution to climate change. However, biodiesel stability remains a challenging problem in biofuel use in the global energy matrix. In this context, organic additives have been investigated to minimize these problems and reduce harmful emissions to comply with fuel requirement standards. In this study, we discuss a comprehensive structural description, a behavior of B15 [85% volume of diesel and 15% volume of biodiesel (B100)] stability in the presence of antioxidants (chalcone analogues), and a theoretical calculation to pave the way for clarifying and expanding the potential of title compounds as an antioxidant additive for diesel–biodiesel blends. Finally, a systematic description of the oxidation stability was undertaken using a specialized machine learning computational pySIRC platform.
- ItemInsights on a new sulfonamide chalcone with potential antineoplastic application(2021) Wenceslau, Patricia Rafaella Santana; Paula, Renata Layse Gonçalves de; Duarte, Vitor Santos; D´Oliveira, Giulio Demetrius Creazzo; Guimarães, Laura Maria Marques; Noda Pérez, Caridad; Borges, Leonardo Luiz; Martins, José Luís Rodrigues; Fajemiroye, James Oluwagbamigbe; Franco, Chris Hebert de JesusChalcones (E)-1,3-diphenyl-2-propene-1-ones, a class of biosynthetic precursor molecules of flavonoids, have a wide variety of biological applications. Besides the natural products, many synthetic derivatives and analogs became an object of continued interest in academia and industry. In this work, a synthesis and an extensive structural study were performed on a sulfonamide chalcone 1-Benzenesulfonyl-3-(4-bromobenzylidene)-2-(2-chlorophenyl)-2,3-dihydro-1H-quinolin-4-one with potential antineoplastic application. In addition, in silico experiments have shown that the sulfonamide chalcone fits well in the ligand-binding site of EGFR with seven μ-alkyl binding energy interactions on the ligand-binding site. Finally, the kinetic stability and the pharmacophoric analysis for EGFR indicated the necessary spatial characteristics for potential activity of sulfonamide chalcone as an antagonist.
- ItemInsights on sustainable fuels: a new benzimidazole derivative with potential as a diesel-biodiesel blend additive(2023) Duarte, Vitor Santos; Naves, Raquel Ferreira; Bortoluzzi, Adailton João; Faria, Eduardo Coelho da Mata; Magalhães, Aline da Silva; Mori, Vânia; Alonso, Christian Gonçalves; Oliveira, Guilherme Roberto de; Napolitano, Hamilton BarbosaBiodiesel is an important fuel in the energy industry with recurrent durability and stability problems. The use of molecular-based technologies to preserve the physicochemical properties of diesel-biodiesel blend is a promising path on additive studies. To minimize oxidative stability problems and get insights into the additive structural features, we evaluated a new benzimidazole derivative as a potential additive for diesel-biodiesel blends. In the study, an extensive structural description and supramolecular topological analysis, besides theoretical calculations to understand specific physicochemical properties related to oxidative stability when added to biofuel, were carried out. Also, the synthesis of the title compound in the presence of graphite oxide shows a sustainable synthetic route, and the supramolecular arrangement has only C–H···O and C–H···π interactions that are related to antibacterial and antioxidant activity. The new benzimidazole derivative structure has two alkoxy groups in the para position of the aromatic ring acting as electron-donating substituents – desirable conformations for antioxidant activity. The energy of 640.99 kJ/mol in the Frontier Molecular Orbitals indicates high kinetic stability and the oxidative stability in the diesel-biodiesel blend (B20) was 26.3 h (better than commercial additives). The obtained results indicate the potential of benzimidazole derivative as a diesel-biodiesel blend additive.
- ItemA new halogen-chalcone with potential for application in biofuels(2020) Faria, Eduardo Coelho da Mata; Duarte, Vitor Santos; Silva, Aline Magalhães da; Fernandes, Fernanda de Sousa; Oliveira, Guilherme Roberto de; Napolitano, Hamilton BarbosaFossil fuels, which represent an important villain for the terrestrial ecosystem, are non-renewable sources of energy, which prompt many discussions about how long petroleum will remain available for use. As an alternative, new energy sources have been explored, including biofuels, such as biodiesel and ethanol. However, their use can raise some problems, such as lower storage stability associated with poor oxidation stability and lower energy availability, which affect consumption, emissions, and energy efficiency. In this context, a comprehensive study with structural description, theoretical calculations, and calorific power test was performed for a new halogen chalcone 4-(4-chlorophenyl)-1-[4-(2-oxo-2-phenylethoxy)phenyl]butan-2-one to understand its supramolecular arrangement and physicochemical properties. The structural description was carried out by X-ray diffraction with the contribution of Hirshfeld surfaces. The theoretical calculations were carried out using density functional theory with the contribution of calorific power determined by a calorimetric pump. All observed results characterize the new chalcone as a potential additive for biofuels.
- ItemA new quinolinone-chalcone hybrid with potential antibacterial and herbicidal properties using in silico approaches(2022) Duarte, Vitor Santos; Paula, Renata Layse Gonçalves de; Custodio, Jean Marcos Ferreira; D´Oliveira, Giulio Demetrius Creazzo; Borges, Leonardo Luiz; Noda Pérez, Caridad; Perjesi, Pal; Oliver, Allen G.; Napolitano, Hamilton BarbosaQuinolinone-chalcones are hybrid compounds consisting of chalcone and quinolone moieties with biological activity related to their hybrid structure. This work seeks to describe the structural and theoretical parameters related to the physicochemical properties and biological activity of a new quinolinone-chalcone. The synthesis, structural characterization by X-ray diffraction, molecular topology by Hirshfeld surfaces and QTAIM, molecular electronic calculations, and pharmacophore analysis were described. The weak interactions C–H…O, C–H…π, and C–H…Br were responsible for crystal growth and stabilized the crystalline state. The DFT analysis shows that the sulfonamide group region is susceptible to observed interactions, and the frontier molecular orbitals indicate high kinetic stability. Also, pharmacophore analysis revealed potential antibacterial and herbicidal activity; by docking within the active site of TtgR, a transcription regulator for the efflux pump TtgABC from the highly resistant Pseudomonas putida (P. putida) strain DOT-TIE, we showed that the activation of TtgR relies upon the binding of aromatic-harboring compounds, which plays a crucial role in bacterial evasion. In this context, a new quinolinone-chalcone has a higher binding affinity than tetracycline, which suggests it might be a better effector for TtgR.
- ItemSynthesis, crystal structure and molecular modeling of a novel Chalcone-Quinolone Hybrid(2020) Paula, Renata Layse Gonçalves de; Carvalho, Fernanda Borges; D´Oliveira, Giulio Demetrius Creazzo; Duarte, Vitor Santos; Santin, Lauriane Gomes; Noda Pérez, Caridad; Oliveira, Solemar Silva; Napolitano, Hamilton BarbosaChalcones and their analogues have been found in nature or synthesized, and several biological activities have been reported to this class of compounds. A comprehensive study on molecular modeling and structural description were performed for a new chalcone-quinolinone hybrid 1-Benzenesulfonyl-3-(4-bromo-benzylidene)-2-(2-ethoxy-phenyl)-2,3-dihydro-1H-quinolin-4-one (CQH) in order to get a better understanding about its supramolecular arrangement and physicochemical properties. Moreover, the crystal structure, molecular interactions and supramolecular arrangement were described by X-ray diffraction with the contribution of Hirshfeld surfaces, and topological analysis to observed molecular interactions was performed by Quantum Theory of Atoms in Molecules (QTAIM). Finally, the electronic study for differences between the solid and gas phases was carried out by Car-Parrinello Molecular Dynamics (CPMD) using Density Functional Theory (DFT).