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1.
J Fluoresc ; 2024 Oct 16.
Artigo em Inglês | MEDLINE | ID: mdl-39412725

RESUMO

This study reveals the solvent dependent third-order nonlinear optical (NLO) features of malachite green (MG) dye using Z-scan technique. MG dye is dissolved in polar solvents, including DMF, DMSO, ethanol, acetone, methanol, and 1-propanol. The study employs the Z-scan instrument, using a continuous wave (CW) laser as the excitation source, operating at a wavelength of 650 nm. The closed aperture (CA) and open aperture (OA) Z-scan techniques are used to assess the nonlinear indices of refraction (n2) and nonlinear coefficient of absorption (ß) of MG dye. MG dye demonstrates both saturable absorption (SA) and reverse saturable absorption (RSA) in the OA Z-scan results, due to negative and positive NLO absorption coefficients. MG dye proves a self-defocusing NLO refractive index while operating under low-power conditions. The third-order NLO susceptibility (χ3) of MG dye in various liquids are calculated to be the order of 10-6 esu. Multilinear regression fit is applied here to investigate the various intermolecular interactions between the solute and solvent. MG dye exhibited large thermo-optic coefficient of the order of 10- 3 K- 1 is observed. The results give important new information about the characteristics of MG dye and indicate potential sources of material for NLO applications in future.

2.
Environ Res ; 260: 119568, 2024 Nov 01.
Artigo em Inglês | MEDLINE | ID: mdl-38971357

RESUMO

The aim of this study was to synthesize effective and economical MoS2/CdNi@rGO photocatalysts and investigate their performance in the degradation of organic pollutants in synthetic effluent. The objective was to assess the characterization results of the synthesized photocatalysts using XRD, SEM/EDS, TEM/HR-TEM, Raman spectrum, and BET isotherm analysis tools. These analyses revealed the good adhesion of MoS2 with rGO and provided insights into the structure and properties of the materials. The results showed that the MoS2/CdNi@rGO photocatalysts exhibited remarkable degradation efficiency for organic pollutants such as Rhodamine-B, erichrome black, and malachite green. The outcomes of the study demonstrated that the MoS2/CdNi@rGO catalyst had the greatest rate constant for Rhodamine-B (RhB) decomposition. which would have been approximately 33 times higher than that of pure RGO (0.0121 min-1). The MoS2/CdNi@rGO photocatalysts also showed excellent recyclability and persistence across five recycle assays, indicating their potential for practical applications in wastewater treatment. The photocatalyst was moderately active, stable up to its fifth usage and stability of the photocatalyst before and after the photocatalytic reaction was also been studied using XRD and SEM. Further research in this area could lead to the development of advanced photocatalytic technologies for environmental remediation.


Assuntos
Dissulfetos , Molibdênio , Poluentes Químicos da Água , Poluentes Químicos da Água/química , Poluentes Químicos da Água/análise , Molibdênio/química , Dissulfetos/química , Catálise , Grafite/química
3.
Environ Res ; 242: 117761, 2024 Feb 01.
Artigo em Inglês | MEDLINE | ID: mdl-38036214

RESUMO

This paper describes a simple phyto-remediation of feather-like silver/copper bi-matrix (BMs) was constructed by employing pommagrant waste peel (PWP) extract as crucial role of reducing agent and chelating agents. Numerous strategies, including UV-Visible, XRD, SEM-EDX, and TEM and BET isotherm were used to analysis the optical, structural, surface area and functional properties. Ag/Cu BPNMs of TEM characterization shows feather-like architectural features with constrained size and shape. The Ag/Cu co-catalytic nanoparticles have a particle size of 34-64 nm. The photocatalytic efficiency of Ag/Cu BMs was investigated using a garment dye, Congo red (CR), at successive time intervals under halogen lamp exposure. For Ag/Cu bimetallic nanoparticles, the photocatalytic degradation rate was recorded to be 100% after 40 min which is caused by adsorption of Congo red dye molecules on Ag/Cu and their degradation by reactive oxygen species (ROS). ROS are free hydroxyl radicals such as •OH and O2• ions that have high oxidizing capacity. The developed Ag/Cu BMs shown effective bacteriostatic action against many infections.


Assuntos
Vermelho Congo , Nanopartículas Metálicas , Animais , Cobre/química , Plumas , Espécies Reativas de Oxigênio , Vestuário , Nanopartículas Metálicas/química
4.
Environ Res ; 259: 119479, 2024 Oct 15.
Artigo em Inglês | MEDLINE | ID: mdl-38964575

RESUMO

This study investigates the use of Excoecaria agallocha leaves as a bio-template for the intercalation of Selenium nanoparticles (SeNPs). The synthesized SeNPs were characterized using techniques like SEM-EDX, TEM/HR-TEM, and XRD spectroscopic studies. The study found that SeNPs showed maximum cleaning ability at a dosage of 50 µl/mL, with 95% inhibition of DPPH radicals. However, cellular absorption was limited to 55% at concentrations of 300 µg/L over a 72-h period. The synthesized SeNPs also demonstrated a strong cytotoxic effect on MCF-7 breast cancer cell lines, indicating their potential as anti-cancer agents. Further research is needed to fully explore the potential of these novel nanocomposites.


Assuntos
Antibacterianos , Antioxidantes , Selênio , Humanos , Selênio/química , Selênio/farmacologia , Antioxidantes/farmacologia , Antioxidantes/química , Antibacterianos/farmacologia , Antibacterianos/química , Células MCF-7 , Nanopartículas Metálicas/química , Folhas de Planta/química , Nanopartículas/química , Poluentes Ambientais/toxicidade
5.
Environ Res ; 242: 117625, 2024 Feb 01.
Artigo em Inglês | MEDLINE | ID: mdl-38007079

RESUMO

Ecologically inspired to develop silver, gold and silver/gold bimetallic nanoparticles from discarded orange peel extract. The plant-derived compounds included in discarded orange peel extract have been accountable for the development of Ag, Au and Ag-Au bimetallic nanoparticles, that might be used in the biosynthetic process. The qualitative assessment of developed silver, gold and silver/gold bimetallic nanoparticles has been performed by UV-visible, XRD pattern, FT IR analysis, TEM/HRTEM, EDX and BET isotherm analysis. In this investigation, the photocatalytic effect of developed silver, gold and silver/gold bimetallic nanoparticles on Congo red dye breakdown efficiency was achieved at 96%, 94%, and 99.2%, respectively. Due to prolonged electron-hole recombination process was investigated using UV irradiation and reused for up to 5 consecutive runs without significant loss of photocatalytic activity. Moreover, silver, gold, and silver/gold bimetallic nanoparticles manufactured in an environmentally benign manner could potentially contribute to the ecological cleanup.


Assuntos
Citrus sinensis , Nanopartículas Metálicas , Prata , Vermelho Congo , Citrus sinensis/metabolismo , Carcinógenos , Ouro , Extratos Vegetais
6.
Environ Res ; 259: 119445, 2024 Oct 15.
Artigo em Inglês | MEDLINE | ID: mdl-38942259

RESUMO

In present investigation, Carica papaya leaf extract has been employed as a bio-reductant agent in order to synthesize ecologically sustainable bio-coupled gold nanoparticles. The formation of gold nanoparticles was confirmed based on colour change of solution and its surface plasmon resonance peak measured using UV-Vis Spectrophotometer (UV-Vis). The Morphology and size of nanoparticles were determined using transmission electron microscope (SEM/TEM), and its crystalline structure by X-ray diffraction studies. Surface area was determined via BET isotherm analysis. The elemental composition of Au nanoparticles was developed using the technique of energy dispersive spectroscopy (EDS). Furthermore, FTIR analysis delineated the presence of functional groups present in the samples of the synthesized AuNPs. Thus, the efficiency of bio coupled Au nanoparticles in photo catalytically decomposing methylene blue was examined under the influence of visible light., the lethal MB colorant had been reduced to 95 % Within 90 min. And also 60% TOC removal was recorded after 5 min of degradation reaction, which increased to 99% after 90 min. Furthermore, cytotoxic experiments on Michigan Cancer Foundations-7 (MCF-7) cell lines showed that Au nanoparticles are effective anticancer agents with an IC50 of 87.2 g/mL on the top of the present work revealed the eco-safety and affordable production of Au nanoparticles from Carica papaya leaf extract, which displayed photocatalytic debasement of organic pollutants and cyto-toxicity effects was investigated.


Assuntos
Carica , Flavonoides , Ouro , Nanopartículas Metálicas , Extratos Vegetais , Folhas de Planta , Ouro/química , Nanopartículas Metálicas/química , Folhas de Planta/química , Carica/química , Extratos Vegetais/química , Flavonoides/análise , Flavonoides/química , Humanos , Células MCF-7 , Azul de Metileno
7.
Environ Res ; 251(Pt 2): 118728, 2024 Jun 15.
Artigo em Inglês | MEDLINE | ID: mdl-38492840

RESUMO

Affordable and swiftly available h-BN@SnO2/TiO2 photocatalysts are being developed through an easy hydrothermally approach was used urea as boric acid precursors. With their constructed photo catalysts, the effect of h-BN@SnO2/TiO2 has been investigated under the assessment of Adsorption agents utilizing X-ray diffraction pattern (XRD), Scanning electron microscopy, Energy dispersive spectroscopic analysis (SEM/EDS), transmission electron microscopy (TEM), high resolution transmission electron microscopy (HR-TEM), and Burner Emit Teller (BET) isotherm testing methods, which also indicated that SnO2/TiO2 and h-BN have been tightly bound together. Because turquoise blue (TB) and Methyl orange (MO) fabric dyes can be found in the industrial wastewater being processed, the photo catalytic degradation process happens to be applied. According to the advantageous linkages of h-BN@SnO2/TiO2 photocatalysts, fantastic efficacy in breakdown towards hazardous compounds has been found. For the decomposition of Turquoise blue (TB) and Methyl orange (MO), the h-BN@SnO2/TiO2 catalysts proved the best performance stability (0.0386 min-1 and 1.524min-1) but were significantly 22 times quicker. Optical catalysis has additionally demonstrated extraordinary resilience and durability throughout five reprocessed efforts. On top of that, an approach enabling photocatalytic breakdown of harmful substances upon h-BN@SnO2/TiO2 has been presented.


Assuntos
Corantes , Compostos de Estanho , Titânio , Águas Residuárias , Poluentes Químicos da Água , Titânio/química , Poluentes Químicos da Água/química , Poluentes Químicos da Água/análise , Corantes/química , Compostos de Estanho/química , Águas Residuárias/química , Catálise , Eliminação de Resíduos Líquidos/métodos , Purificação da Água/métodos , Têxteis/análise , Fotólise
8.
Biotechnol Appl Biochem ; 71(3): 512-524, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38253987

RESUMO

The contemporary food industry's uses of nanoemulsions (NEs) include food processing, effective nutraceutical delivery, the development of functional chemicals, and the synthesis of natural preservatives, such as phytocompounds. Although cinnamon essential oil (CEO) is widely used in the cosmetic, pharmaceutical, and food industries, it is difficult to add to aqueous-based food formulations due to its weak stability and poor water solubility. This study describes the formulation of a CEO nanoemulsion (CEONE) by spontaneous emulsification and evaluates its antibacterial and antibiofilm properties against biofilm-forming Serratia rubidaea BFMO8 isolated from spoiled emperor fish (Lethrinus miniatus). Bacteria causing spoilage in emperor fish were isolated and identified as S. rubidaea using common morphological, cultural, and 16S RNA sequencing methods, and their ability to form biofilms and their susceptibility to CEONE were assessed using biofilm-specific methods. The spontaneous emulsification formulation of CEONE was accomplished using water and Tween 20 surfactant by manipulating organic and aqueous phase interface properties and controlling particle growth by capping surfactant increases. The best emulsification, with highly stable nano-size droplets, was accomplished at 750 rpm and a 1:3 ratio concentration. The stable CEONE droplet size, polydispersity index, and zeta potential values were 204.8 nm, 0.115, and -6.05 mV, respectively. FTIR and high-resolution liquid chromatography-mass spectrometry (HR-LCMS) analyses have revealed carboxyl, carbonyl, and phenol-like primary phytochemical functional groups in CEO and CEONE, which contribute to their antibacterial and antibiofilm properties.


Assuntos
Antibacterianos , Biofilmes , Cinnamomum zeylanicum , Emulsões , Óleos Voláteis , Serratia , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Biofilmes/efeitos dos fármacos , Antibacterianos/farmacologia , Antibacterianos/química , Emulsões/química , Emulsões/farmacologia , Cinnamomum zeylanicum/química , Serratia/química , Serratia/efeitos dos fármacos , Serratia/metabolismo , Animais , Testes de Sensibilidade Microbiana , Peixes/microbiologia
9.
Molecules ; 29(5)2024 Feb 21.
Artigo em Inglês | MEDLINE | ID: mdl-38474443

RESUMO

Employing naturally extracted dyes and their derivatives as photosensitizers towards the construction of dye-sensitized solar cells (DSSCs) has been recently emerging for establishing sustainable energy conversion devices. In this present work, Rhodobacter Sphaeroides Photobacteria (Rh. Sphaeroides) was used as a natural source from which Bacteriopheophytine-a (Bhcl) dye was extracted. Further, two cationic derivatives of Bhcl, viz., Guanidino-bacteriopheophorbide-a (Gua-Bhcl) and (2-aminoethyl)triphenylphosphono-bacteriopheophorbide-a (2AETPPh-Bhcl) were synthesized. The thus obtained Bhcl, Gua-Bhcl and 2AETPPh-Bhcl were characterized using liquid chromatography-mass spectrometry (LC-MS) and their photophysical properties were investigated using excitation and emission studies. All three near-infrared (NIR) responsive dyes were employed as natural sensitizers towards the construction of DSSC devices, using platinum as a photocathode, dye-sensitized P25-TiO2 as a photoanode and I-/I3- as an electrolyte. DSSCs fabricated using all three dyes have shown reasonably good photovoltaic performance, among which 2AETPPh-Bhcl dye has shown a relatively higher power conversion efficiency (η) of 0.38% with a short circuit photocurrent density (JSC) of 1.03 mA cm-2. This could be attributed to the dye's natural optimal light absorption in the visible and NIR region and uniform dispersion through the electrostatic interaction of the cationic derivatives on the TiO2 photoanode. Furthermore, the atomic force microscopy studies and electrochemical investigations using cyclic voltammetry, electrochemical impedance spectroscopy and Bode's plot also supported the enhancement in performance attained with 2AETPPh-Bhcl dye.

10.
Environ Res ; 214(Pt 1): 113743, 2022 11.
Artigo em Inglês | MEDLINE | ID: mdl-35772503

RESUMO

The RGO-supported HoVO4-ZnO nanocomposite was synthesized using the ultra sonication process. X-ray diffraction patterns, Field emission scanning electron microscopy, high resolution transmission electron microscopy, Diffractive Reflectance spectroscopy, and photoluminescence spectroscopy were employed to examine the heterostructured photocatalyst in this research study. The photocatalytic efficiency of the RGO-supported HoVO4-ZnO nanoparticles, under UV light irradiation, in the degradation of Rhodamine-B dye was investigated. Undoped ZnO, bare HoVO4, and HoVO4 -ZnO, degraded at 55.6, 57.5, and 74.33 percent in 45 min, respectively. This new RGO coupled HoVO4-ZnO exhibits enhanced photocatalytic efficiency compared to the bare ZnO and HoVO4-ZnO nanocomposite.


Assuntos
Óxido de Zinco , Catálise , Grafite , Rodaminas , Ultrassom
11.
Org Biomol Chem ; 19(5): 1060-1065, 2021 02 11.
Artigo em Inglês | MEDLINE | ID: mdl-33416820

RESUMO

We have developed a one-pot, three-component, and solvent-free reaction for the synthesis of 3-aminofurans using a calcium catalyst. In this cascade reaction, the key intermediate, C,N-diacyliminium ion, is formed in situ from glyoxal and lactam, which further reacted with phenolic nucleophiles to form furan derivatives in good yields with broad substrate diversity. We also present here the preliminary photophysical studies of selected compounds.

12.
Bioorg Chem ; 110: 104798, 2021 05.
Artigo em Inglês | MEDLINE | ID: mdl-33735710

RESUMO

Novel spirooxindolopyrrolidine embedded indandione heterocyclic hybrids were obtained in excellent yields via a regio- and stereoselective one-pot three component reaction between Baylis-Hillman adduct and non-stabilized azomethine ylides. The structure of newly synthesized compounds was elucidated through 1D and 2D spectroscopic data and the stereochemistry was determined by single crystal X-ray diffraction analysis. In vitro tubercular activity against Mycobacterium tuberculosis H37Rv using MABA assay reveals that the compound bearing chlorine substituted on the oxindole ring displayed the most potent activity with MIC 0.78 µg/mL and is two-fold active than the standard drug, ethambutol (MIC 1.56 µg/mL).


Assuntos
Antibacterianos/farmacologia , Indanos/farmacologia , Mycobacterium tuberculosis/efeitos dos fármacos , Oxindóis/farmacologia , Pirrolidinas/farmacologia , Compostos de Espiro/farmacologia , Antibacterianos/síntese química , Antibacterianos/química , Relação Dose-Resposta a Droga , Descoberta de Drogas , Indanos/síntese química , Indanos/química , Testes de Sensibilidade Microbiana , Estrutura Molecular , Oxindóis/síntese química , Oxindóis/química , Pirrolidinas/síntese química , Pirrolidinas/química , Compostos de Espiro/síntese química , Compostos de Espiro/química , Estereoisomerismo , Relação Estrutura-Atividade
13.
Molecules ; 27(1)2021 Dec 27.
Artigo em Inglês | MEDLINE | ID: mdl-35011374

RESUMO

Quinoline Schiff bases display potential applications in optoelectronics and laser fields because of their unique optical properties that arise from extensive delocalization of the electron cloud, and a high order of non-linearity. In this context, a new class of conjugated quinoline-derivative viz. N-(quinolin-3-ylmethylene)anilines were synthesized from 2-hydroxyquinoline-3-carbaldehyde in two good yielding steps. The ability of these imines to accept an electron from a donor is denoted by their electron acceptor number and sites, which is calculated using density functional theory (DFT). The optical properties such as FT-IR, Raman, UV-VIS, and EDS spectra were calculated using TD-DFT, which also provided the energy gap, HOMO-LUMO structure. The optical properties of the synthesized imino quinolines were experimentally studied using photoluminescence and absorption spectroscopy. The properties such as Stokes shift and quantum yield were calculated using experimental data. Furthermore, the compound bearing a methyl group on the aryl ring and ZnO nanoparticles (hydrothermally synthesized) were dissolved in toluene, and optically excited with a 355 nm nanosecond laser, which produced a random laser.

14.
Bioorg Med Chem Lett ; 30(2): 126789, 2020 01 15.
Artigo em Inglês | MEDLINE | ID: mdl-31753696

RESUMO

A small library of structurally fascinating spiropyrrolidine tethered imidazole heterocylic hybrids has been synthesized regioselectively in good yields employing [bmim]Br mediated 1,3-diplar cycloaddition strategy. The new class of azomethine ylide generated in situ from l-histidine and 11H-indeno[1,2-b]quinoxalin-11-one reacts with various substituted ß-nitrostyrenes affording the spiropyrrolidine tethered imidazole heterocylic hybrids. Compounds thus synthesized were assessed for their in vitro cholinesterase (ChEs) inhibitory activities, among them compounds possessing 4-methyl and 4-methoxy substituents on the aryl ring showed potent activities with IC50 values of 2.02 ±â€¯0.05 and 2.05 ±â€¯0.06 µM against AChE and 12.40 ±â€¯0.14 and 11.45 ±â€¯0.28 µM against BChE enzyme, respectively. In addition, the most active compounds were performed for their molecular docking simulation and the results revealed interesting binding templates to the active site channel of cholinesterase enzymes.


Assuntos
Acetilcolinesterase/metabolismo , Butirilcolinesterase/metabolismo , Desenho de Fármacos , Imidazóis/química , Pirrolidinas/química , Compostos de Espiro/química , Acetilcolinesterase/química , Sítios de Ligação , Butirilcolinesterase/química , Domínio Catalítico , Inibidores da Colinesterase/síntese química , Inibidores da Colinesterase/metabolismo , Reação de Cicloadição , Humanos , Concentração Inibidora 50 , Simulação de Acoplamento Molecular , Relação Estrutura-Atividade
15.
Bioorg Chem ; 100: 103865, 2020 07.
Artigo em Inglês | MEDLINE | ID: mdl-32361055

RESUMO

Invasive fungal infections along with rising incidence of resistance to antifungal drugs pose increasing threat to immunocompromised individuals, including cancer patients. In this study, we examined the antifungal activity of dispiropyrrolidine tethered piperidone heterocyclic hybrids. Results indicate that compounds 5a and 6i have demonstrated a potent antifungal effect on multiple fungal strains, including Candida albicans, without exhibiting cytotoxicity to mammalian cells. Furthermore, these two compounds exhibited significant inhibition on Candida albicans hyphae and biofilm development that surpasses the FDA-approved antifungal drug currently used for treatment. Taken together, our results suggest that 5a and 6i are promising candidates for development into new antifungal drugs.


Assuntos
Antifúngicos/química , Antifúngicos/farmacologia , Candida albicans/efeitos dos fármacos , Cryptococcus neoformans/efeitos dos fármacos , Piperidonas/química , Piperidonas/farmacologia , Antifúngicos/síntese química , Candidíase/tratamento farmacológico , Candidíase/microbiologia , Linhagem Celular , Criptococose/tratamento farmacológico , Criptococose/microbiologia , Humanos , Modelos Moleculares , Piperidonas/síntese química , Pirrolidinas/síntese química , Pirrolidinas/química , Pirrolidinas/farmacologia
16.
Bioorg Chem ; 99: 103799, 2020 06.
Artigo em Inglês | MEDLINE | ID: mdl-32247109

RESUMO

A series of structurally intriguing novel class of spiropyrrolidine tethered quinoxaline heterocyclic hybrids has been achieved in excellent yields employing ionic liquid accelerated multicomponent 1,3-dipolar cycloaddition reaction strategy. ß-Nitrostyrenes were used as dipolarophiles, while the 1,3-dipole component was the azomemthine ylide, generated in situ from indenoquinoxaline and l-phenylalanine. The reaction provided three new bonds and four contiguous stereocenter with full distereomeric control. In vitro activity of these spiroheterocyclic hybrids against Mycobacterium tuberculosis H37Rv using MABA assay revealed that the compound with nitro group on the phenyl ring is the most active candidate (1.56 µg/mL) among the other analogues of the series and has an activity similar to that of the standard drug, Ethambutol.


Assuntos
Antituberculosos/farmacologia , Compostos Heterocíclicos/farmacologia , Mycobacterium tuberculosis/efeitos dos fármacos , Pirrolidinas/farmacologia , Quinoxalinas/farmacologia , Compostos de Espiro/farmacologia , Antituberculosos/síntese química , Antituberculosos/química , Relação Dose-Resposta a Droga , Compostos Heterocíclicos/síntese química , Compostos Heterocíclicos/química , Testes de Sensibilidade Microbiana , Estrutura Molecular , Pirrolidinas/síntese química , Pirrolidinas/química , Quinoxalinas/síntese química , Quinoxalinas/química , Compostos de Espiro/síntese química , Compostos de Espiro/química , Relação Estrutura-Atividade
17.
Molecules ; 25(23)2020 Nov 27.
Artigo em Inglês | MEDLINE | ID: mdl-33261115

RESUMO

With an aim to develop more effective and affordable anticancer agents possessing a unique mechanism of action, we designed and synthesized derivatives of spirooxindole-pyrrolidine heterocyclic hybrids in good yields through a one-pot three-component (3+2) cycloaddition strategy. The synthesized compounds were characterized thoroughly for the physicochemical properties by making use of FT-IR, NMR spectroscopy, and mass spectrometry. Further, these compounds have been evaluated for the influence of anticancer activity against HepG2 cells up to 200 µg/mL concentration. The highly active molecular scaffold was tested for the in-depth mechanistic studies, and it was found that the major pathway of cell death is apoptosis which occurs through the induction of reactive oxygen species followed by the involvement of caspases.


Assuntos
Antineoplásicos/química , Antineoplásicos/farmacologia , Compostos Heterocíclicos/química , Pirrolidinas/química , Compostos de Espiro/química , Apoptose , Proliferação de Células , Reação de Cicloadição , Células Hep G2 , Humanos , Técnicas In Vitro , Estrutura Molecular , Relação Estrutura-Atividade
18.
Molecules ; 25(20)2020 Oct 18.
Artigo em Inglês | MEDLINE | ID: mdl-33080968

RESUMO

Our synthetic approach for the assembly of structurally complex spirooxindole heterocyclic hybrids was based on an ionic liquid, [bmim]Br mediated one-pot three-component cascade reaction strategy involving 1,3-dipolar cycloaddition reaction of N-1-(2-pyridinylmethyl)-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones and azomethine ylide generated in situ from isatin and L-phenyl alanine, affording a series of spirooxindole-pyrrolidine heterocyclic hybrids in good-to-excellent yields. In addition to serving as the reaction medium, [bmim]Br also functioned as a catalyst in this cycloaddition reaction and hence accelerated the reaction rate affording the cycloadducts in short reaction time.


Assuntos
Compostos Heterocíclicos/química , Líquidos Iônicos/química , Isatina/química , Piridonas/química , Compostos de Espiro/química , Compostos Azo/química , Reação de Cicloadição , Compostos Heterocíclicos/síntese química , Indóis/química , Estrutura Molecular , Oxindóis/química , Pirrolidinas/química , Tiossemicarbazonas/química
19.
Bioorg Med Chem Lett ; 29(5): 729-733, 2019 03 01.
Artigo em Inglês | MEDLINE | ID: mdl-30655213

RESUMO

Fungal infections caused by Candida and Cryptococcus are particularly dangerous for immunocompromised individuals. In this study, we identified that benzimidazole fused pyrrolo[3,4-b]quinoline compounds have potent antifungal activity against several clinical isolates of pathogenic fungal strains. Specifically, the compound 6a did not show cytotoxicity against mammalian cells at a concentration that inhibits the growth of fungal strains. In addition, the compound 6a also significantly reduced the metabolic activity of fungal cells in the Candida albicans biofilms. Collectively, our results indicate that benzimidazole fused quinoline compounds have a potential to develop as an antifungal agents.


Assuntos
Antifúngicos/farmacologia , Benzimidazóis/química , Candida albicans/efeitos dos fármacos , Cryptococcus/efeitos dos fármacos , Pirróis/química , Quinolinas/química , Biofilmes/efeitos dos fármacos , Testes de Sensibilidade Microbiana
20.
Bioorg Med Chem Lett ; 29(16): 2059-2063, 2019 08 15.
Artigo em Inglês | MEDLINE | ID: mdl-31320146

RESUMO

Invasive fungal infections are one of the leading causes of nosocomial bloodstream infections with a limited treatment option. A series of derivatized spirooxindolo-pyrrolidine tethered indole and imidazole heterocyclic hybrids have been synthesized, and their antifungal activity against fungal strains were determined. Here we characterize the antifungal activity of a specific spirooxindolo-pyrrolidine hybrid, dubbed compound 9c, a spirooxindolo-pyrrolidine tethered imidazole synthesized with a 2-chloro and trifluoromethoxy substituent. The compound 9c exhibited no cytotoxicity against mammalian cell line at concentrations that inhibited fungal strains. Compound 9c also significantly inhibited the fungal hyphae and biofilm formation. Our results indicate that spirooxindolo-pyrrolidine heterocyclic hybrids potentially represent a broad class of chemical agents with promising antifungal potential.


Assuntos
Antifúngicos/farmacologia , Imidazóis/farmacologia , Indóis/farmacologia , Pirrolidinas/farmacologia , Compostos de Espiro/farmacologia , Antifúngicos/síntese química , Antifúngicos/toxicidade , Biofilmes/efeitos dos fármacos , Candida/efeitos dos fármacos , Candida/fisiologia , Linhagem Celular Tumoral , Cryptococcus/efeitos dos fármacos , Cryptococcus/fisiologia , Humanos , Imidazóis/síntese química , Imidazóis/toxicidade , Indóis/síntese química , Indóis/toxicidade , Testes de Sensibilidade Microbiana , Pirrolidinas/síntese química , Pirrolidinas/toxicidade , Compostos de Espiro/síntese química , Compostos de Espiro/toxicidade
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