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1.
Food Chem ; 399: 133901, 2023 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-36001927

RESUMO

In this study, a novel supramolecular solvent based on surface-active ionic liquid was prepared and used as an extraction solvent for dispersive liquid-liquid microextraction of four triazine herbicides in tea samples. The formation mechanism, microstructure and physicochemical properties of supramolecular solvent were studied. Some parameters, including the molar ratio of surface-active ionic liquid to tetrahydrofuran, volume of supramolecular solvent, vortex time, pH of sample solution, type and amount of salt, were investigated and optimized. The good linearities (r > 0.9990) for the analytes were obtained. The limits of detection and quantification for triazine herbicides were in the range of 1.7-2.1 µg kg-1 and 5.6-7.1 µg kg-1, respectively. The spiked recoveries were 80.0-119.9 %. The supramolecular solvent prepared in this study has the advantages of simple preparation process, low viscosity and good dispersibility. It can be used for the extraction and enrichment of trace triazine herbicides in tea samples.


Assuntos
Herbicidas , Líquidos Iônicos , Microextração em Fase Líquida , Cromatografia Líquida de Alta Pressão , Herbicidas/análise , Líquidos Iônicos/química , Limite de Detecção , Solventes/química , Chá , Triazinas/análise
2.
Food Chem ; 399: 134010, 2023 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-36058099

RESUMO

A method using ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) was developed for the determination of toxoflavin and fervenulin in 6 types of food.The limits of detection (LODs, S/N ≥ 3) of toxoflavin and fervenulin reached 12 µg/kg and 24 µg/kg, respectively.The recoveries ranged from 70.1 % to 108.7 %.Intra-day RSDs (n = 5) and inter-day RSDs (n = 3) ranged from 0.9 % to 9.5 %.The method was successfully applied to analyse 36 samples, and one Tremella fuciformis Berk. sample was found with 7.5 mg/kg toxoflavin and 3.2 mg/kg fervenulin. Toxoflavin and fervenulin were acidic compounds and easily degraded in 0.1 % ammonia solution (v/v),degradation products were identified by ultra-high performance liquid chromatography-tandem quadrupole time-of-flight mass spectrometry (UHPLC-Q-TOF/MS).


Assuntos
Toxinas Bacterianas , Espectrometria de Massas em Tandem , Cromatografia Líquida de Alta Pressão/métodos , Pirimidinonas , Triazinas
3.
J Hazard Mater ; 444(Pt A): 130366, 2023 02 15.
Artigo em Inglês | MEDLINE | ID: mdl-36434920

RESUMO

As promising visible-light-responsive photocatalysts, triazine-based covalent organic frameworks (CTFs) still suffer from broad bandgap and high electron-hole recombination. As such, different contents of electron-rich ketone group were introduced to CTFs (X % keto-CTF), aiming to clarify the mechanism of quantitatively regulating ketone for enhanced visible-light photocatalytic performance of CTFs. As ketone content increased, the bandgap narrowed, electron-hole recombination decreased, charge transfer and quantum yield increased. As a result, keto-CTF outperformed other keto-CTFs in visible-light photocatalytic degradation of tetracycline, and apparent rate constant of TC (kobs) was 3.69 times higher than that of CTF. Importantly, ketone tuning induced varied types and concentrations of reactive species. Integrated with quantitative structure-activity relationships (QSARs) analysis and density functional theory (DFT) calculations, this study unravels how ketone content regulates bandgap structure of CTF, affects the contribution of varied reactive species, and quantitatively enhances the photocatalytic performance of CTFs. It also provides novel insights into the precise design and synthesis of CTFs-based catalyst structures for high-efficient visible-light photocatalytic degradation of organic pollutants.


Assuntos
Poluentes Ambientais , Estruturas Metalorgânicas , Triazinas , Cetonas , Luz
4.
Bioorg Chem ; 130: 106263, 2023 01.
Artigo em Inglês | MEDLINE | ID: mdl-36375350

RESUMO

Bruton's tyrosine kinase (BTK) is a promising drug target for the treatment of B-cell related malignancies. Irreversible inhibition of BTK by a covalent inhibitor has been proved to be a clinically effective therapy. However, most irreversible BTK inhibitors also inhibit other kinases including JAK3 and EGFR, leading to some adverse events. Herein, we reported the structure-based design and optimization of a series of irreversible BTK inhibitors bearing the 6-amino-1,3,5-triazine scaffold. Most of the synthesized compounds demonstrated considerable BTK inhibition and improved anti-proliferative activity against Raji and Ramos cells. Among them, compound C11 exhibited potent BTK inhibition (BTK IC50 = 17.0 nM) and a desirable selectivity profile especially over EGFR. Moreover, C11 effectively blocked activation of BTK and downstream signaling, arrested the cell cycle in G0/G1 phase and induced apoptosis in Raji cells. Its irreversible binding mode was further investigated by both molecular modeling and a washout experiment. Collectively, C11 is a novel selective irreversible BTK inhibitor worthy of further in-depth research.


Assuntos
Inibidores de Proteínas Quinases , Triazinas , Inibidores de Proteínas Quinases/química , Estrutura Molecular , Relação Dose-Resposta a Droga , Tirosina Quinase da Agamaglobulinemia , Relação Estrutura-Atividade , Triazinas/farmacologia , Receptores ErbB/metabolismo
5.
J Hazard Mater ; 444(Pt B): 130428, 2023 02 15.
Artigo em Inglês | MEDLINE | ID: mdl-36435039

RESUMO

Simultaneous regulation of adsorption and photocatalytic performance of covalent triazine frameworks (CTFs) to achieve efficient control of organic pollution in water is a promising strategy, but remains a formidable challenge. Herein, pyridine linkers were innovatively introduced into pristine CTF (p-CTF) and the bidirectional electron donor-acceptor (EDA) system of contaminant-to-pyridine and pyridine-to-triazine was constructed inside. Experimental results combined with theoretical calculations revealed that pyridine units with π-deficient properties performed as electron acceptors and electron donors in the adsorption and photocatalytic processes, respectively. This special structure provided a directional pathway for electron transfer, which endowed CTFs with excellent adsorption and photocatalytic properties. Compared to p-CTF, pyridine-linked CTF (M-CTF) showed a 16-fold increase in adsorption capacity for naphthalene (973.4 µmol·g-1). Benefiting from the optimized light absorption and electron transfer form (n → π*transition), M-CTF exhibited high regeneration efficiency after adsorption of both bisphenol A (94 % after 4 cycles) and naphthalene (95 % after 4 cycles). Besides, the removal performance of organic micropollutants from natural water showed a great advantage thanks to the bidirectional EDA system. Overall, the present study provides new insights into the optimization of electronic structures for carbon-based environmental functional materials applied to organic pollution control in water.


Assuntos
Elétrons , Triazinas , Piridinas , Oxidantes , Naftalenos , Água
6.
Anal Chim Acta ; 1238: 340638, 2023 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-36464452

RESUMO

Sensitive, accurate, and simultaneous determination of nitrobenzene compounds (NBs) in environmental water samples is of great significance due to their high risk to human health. In this work, a new triazine-based hyper-crosslinked polymer named CC-Py was constructed via the Friedel-Crafts reaction between cyanuric chloride (CC), pyridine (Py) and 1,2-dichloroethane. Due to its excellent stability, high surface area and hydrophilic-lipophilic (amphiphilic) structure, the CC-Py exhibited a high affinity toward the NBs (nitrobenzene, 2-nitrotoluene, 2,6-dimethylnitrobenzene, 3-nitrotoluene, 4-nitrotoluene, 3-nitrochlorobenzene, 4-nitrochlorobenzene, 2-nitrochlorobenzene, 2,4-dimethylnitrobenzene, 3-nitrobromobenzene, 4-nitrobromobenzene and 4-nitroiodobenzene). Then, a CC-Py based solid-phase microextraction coupled with gas chromatography-flame ionization detection was developed to detect the twelve NBs in real water samples. The results showed that the method had low limits of detection (0.20-0.50 µg L-1), good reproducibility (relative standard deviations (RSDs) < 8.6%) and high enrichment factors (967-1590). The recoveries for the NBs in six different types of water samples were between 90% and 111% with the RSDs less than 7.5%. This work provides a facile and sensitive method for the determination of trace level of NBs in real water samples.


Assuntos
Polímeros , Triazinas , Humanos , Reprodutibilidade dos Testes , Nitrobenzenos , Água
7.
Bioorg Chem ; 130: 106225, 2023 01.
Artigo em Inglês | MEDLINE | ID: mdl-36335650

RESUMO

Enasidenib (AG-221) is the only approved IDH2 inhibitor, clinical study found Enasidenib have some side-effects. In this work, we synthesized series of novel s-triazine derivatives, and the in vitro and in vivo activity of anti-AML has been studied using AM7577 model. The cell activity found Ta and Th showed excellent inhibition to AM7577. We further used the HuKemia Acute Leukemia xenograft model to investigate the in vivo efficacy of compounds Ta and Th, compared with AG-221, although Ta and Th can't reduce the 2-HG level obviously, those two compounds can prolong the survival of rats. The research can expand the structure of novel IDH2 inhibitors and provide useful information for further research of novel AML drugs.


Assuntos
Isocitrato Desidrogenase , Leucemia Mieloide Aguda , Humanos , Ratos , Animais , Mutação , Aminopiridinas/farmacologia , Triazinas/farmacologia , Triazinas/uso terapêutico , Leucemia Mieloide Aguda/tratamento farmacológico
8.
Bioorg Chem ; 130: 106211, 2023 01.
Artigo em Inglês | MEDLINE | ID: mdl-36343598

RESUMO

Based on 2-(difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole (ZSTK474), three series of novel 1,3,5-triazine or pyrimidine derivatives containing semicarbazones have been designed and synthesized to obtain new potent and selective PI3Kα inhibitors. Their inhibitory activities in vitro were evaluated against PI3Kα and three tumor-derived cell lines (U87-MG, MCF-7, and PC-3). We also tested promising compounds (A4, A6, A10, and B1) for other PI3K class I subtype (PI3Kß, PI3Kδ, and PI3Kγ) activity. The representative compound A10 exhibited an IC50 value of 0.32 nM against PI3Kα, and demonstrated extraordinary subtype selectivity. Furthermore, compound A10 obviously inhibited proliferation of MCF-7 cell lines, induced a great decrease in mitochondrial membrane potential leading to apoptosis of cancer cells, and arrested G2 phase in a dose-dependent manner. Additionally, compound A10 induced significant tumor regressions in a xenograft mouse model of U87-MG cell line without an obvious sign of toxicity upon 20 mg/kg oral administration. Compound A10 may serve as a PI3Kα-selective inhibitor and provide the opportunity to spare patients the side effects associated with broader inhibition of the class I PI3K family.


Assuntos
Antineoplásicos , Humanos , Camundongos , Animais , Inibidores de Fosfoinositídeo-3 Quinase , Relação Estrutura-Atividade , Proliferação de Células , Antineoplásicos/farmacologia , Triazinas/farmacologia , Linhagem Celular Tumoral , Benzimidazóis/farmacologia , Desenho de Fármacos , Ensaios de Seleção de Medicamentos Antitumorais
9.
J Hazard Mater ; 443(Pt B): 130290, 2023 02 05.
Artigo em Inglês | MEDLINE | ID: mdl-36335906

RESUMO

Contamination with energetic compounds (ECs) is common in military sites and poses a great risk to the environment and human health. However, its effects on the soil bacterial communities remain unclear. This study assessed the variations of bacterial communities, co-occurrence patterns, and their influence factors in three types of typical military-contaminated sites (artillery range, military-industrial site, and ammunition destruction site). The results showed that the most polluted sites were ammunition destruction sites, followed by military-industrial sites, whereas pollution in the artillery ranges was minimal. The average concentrations of ECs including 2,4,6-trinitrotoluene (TNT), hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX), and octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) in the study sites ranged 120-1.67 × 105, 20-7.20 × 104, and 180-2.38 × 105 µg/kg, respectively. Bacterial diversity and community structure in military-industrial and ammunition destruction sites were significantly changed, but not in artillery ranges. TNT, pH, and soil moisture are the critical factors affecting bacterial communities in contaminated military sites. Co-occurrence network analysis indicated that the pressure of ECs affected bacterial interactions and microbiota function. Our findings provide new insights into the variations in bacterial communities in EC-contaminated military sites and references for the bioremediation of ECs.


Assuntos
Microbiota , Militares , Poluentes do Solo , Trinitrotolueno , Humanos , Azocinas/análise , Azocinas/química , Biodegradação Ambiental , Triazinas/química , Solo , Poluentes do Solo/análise
10.
Chemosphere ; 310: 136866, 2023 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-36270523

RESUMO

The deposition of explosive contaminants in particulate form onto the soil surface during low-order detonations can lead to ground and surface water contamination. The vertical fate and transport of insensitive munitions formulation IMX-104 through soil has been thoroughly studied, however the lateral transport of explosive particles on the surface is less known. The objective of this research was to understand the impact of overland flow on the transport of IMX-104 constituent compounds 3-nitro-1,2,4-triazol-5-one (NTO), 2,4-dinitroanisole (DNAN), hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX), and octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX). The effect of overland flow was examined in a rill flume using several flow rates (165-, 265-, and 300-mL min-1) and IMX-104 particle sizes (4.75-9.51 mm, 2.83-4.75 mm, 2-2.83 mm, and <2 mm). We found that the smaller particles were transported more in solution and with the sediment compared to the larger particles, which had a higher percent mass remaining on the surface. As flow rate increased, there was an increase in the percent mass found in solution and sediment and a decrease in the percent mass remaining on the surface. NTO fate was dominated by transport in solution, while DNAN, RDX and HMX were predominantly transported with the sediment. This research provides evidence of the role of overland flow in the fate of energetic compounds.


Assuntos
Substâncias Explosivas , Nitrocompostos , Anisóis , Triazinas , Solo
11.
Food Chem ; 403: 134415, 2023 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-36358072

RESUMO

In this work, a new sustainable melamine detection method was developed. Biomass-derived carbon dots (CDs) were successfully prepared by ionic liquid (1-Allyl-3-methylimidazolium chloride, IL) hydrothermal method using agricultural waste corn cob as the carbon source, and combined with silver nanoparticles (AgNPs) to construct fluorescent probe CDs@IL-AgNPs. The probe was characterized and the formation mechanism of the probe was discussed. The direct detection of H2O2 and the indirect sensitive detection of melamine were realized. The detection limit of melamine was 0.94 µmol/L, which is far lower than the minimum allowable amount of melamine in milk powder (7.95 µmol/L). The high sensitivity and selectivity probe was used to detect melamine in commercial dairy products, and the recovery rate of standard addition was between 94 % and 110 %. This study provides valuable new application ideas for the detection of melamine in dairy products and the low-carbon and environmentally friendly treatment of agricultural waste.


Assuntos
Líquidos Iônicos , Nanopartículas Metálicas , Animais , Prata , Corantes Fluorescentes , Peróxido de Hidrogênio/análise , Zea mays , Carbono , Limite de Detecção , Leite/química , Triazinas/análise
12.
Eur Rev Med Pharmacol Sci ; 26(22): 8567-8575, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-36459037

RESUMO

OBJECTIVE: Proteostasis is an important process occurring in all living cells and is highly indispensable for cell survival. The HslVU protease/chaperone complex's critical role in regulating proteostasis to maintain a healthy cellular proteome and its presence in pathogenic microbes made it an important drug target. This study aimed to identify small molecular inhibitors of the HslV protease. MATERIALS AND METHODS: Herein, a library of small molecules belonging to the triazine and chromone families has been evaluated for their inhibitory potential against the E. coli HslV protease using both in silico and in vitro techniques. RESULTS: Four compounds, i.e., SHS-II-123a, SHS-II-147a, US-IV-89, and US-IV-92, were identified as potential inhibitors of the HslV protease having IC50 values in the range of 0.1 to 0.32 µM. Additionally, these compounds' drug-likeness and ADMET profiles indicated their compatibility to be considered safer drug candidates. CONCLUSIONS: To the best of our knowledge, this is the first report on small molecules having inhibitory effects on the HslVU complex. These identified compounds can be efficiently subjected to further investigations to develop novel and safer antimicrobial agents.


Assuntos
Cromonas , Peptídeo Hidrolases , Humanos , Cromonas/farmacologia , Triazinas/farmacologia , Tiazóis , Escherichia coli , Endopeptidases , Chaperonas Moleculares
13.
Pestic Biochem Physiol ; 188: 105263, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-36464368

RESUMO

The leafminer Liriomyza trifolii is an important insect pest of ornamental and vegetable crops worldwide. Cyromazine is an effective, commonly-used insecticide that functions as a growth regulator, but its effect on L. trifolii has not been previously reported. In this study, transcriptome analysis was undertaken in L. trifolii exposed to cyromazine. Clusters of orthologous groups analysis indicated that a large number of differentially expressed genes responding to cyromazine were categorized as "lipid transport and metabolism", "post-translational modification, protein turnover, chaperones", and "cell wall/membrane/envelope biogenesis". Gene ontology analysis indicated that pathways associated with insect hormones, growth and development, and cuticle synthesis were significantly enriched. In general, the transcriptome results showed that the genes related to insect hormones were significantly expressed after treatment with cyromazine. Furthermore, the combined exposure of L. trifolii to cyromazine and the hormone analogues 20-hydroxyecdysone (20E) or juvenile hormone (JH) indicated that hormone analogues can change the expression pattern of hormone-related genes (20EP and JHEH) and pupal length. The combined application of cyromazine with 20E improved the survival rate of L. trifolii, whereas the combination of JH and cyromazine reduced survival. The results of this study help elucidate the mechanistic basis for cyromazine toxicity and provide a foundation for understanding cyromazine resistance.


Assuntos
Dípteros , Hormônios de Inseto , Inseticidas , Animais , Dípteros/genética , Inseticidas/toxicidade , Triazinas/toxicidade , Hormônios Juvenis/farmacologia
14.
Pestic Biochem Physiol ; 188: 105271, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-36464376

RESUMO

The acute toxicity of chlorpyrifos and chlorpyrifos-oxon (organophosphorothioate insecticides) was examined alone and in combination with atrazine (triazine herbicide) and alachlor (chloroacetanilide herbicide) to honey bees (Apis mellifera). Atrazine and alachlor were observed to not be acutely toxic to bees at doses up to 10 and 4 µg per bee, respectively. However, atrazine significantly increased chlorpyrifos toxicity by 3-fold while reducing chlorpyrifos-oxon toxicity by 1.8-fold. These changes in toxicity are correlated with significant 1.3- and 1.2-fold inhibition of acetylcholinesterase (AChE) activity in bees exposed to chlorpyrifos and chlorpyrifos-oxon, respectively. Atrazine significantly increased cytochrome P450, general esterase, and glutathione S-transferase (GST) activities by 1.5-, 1.2-, and 1.2- fold respectively, in bees compared to untreated individuals. Alachlor increased chlorpyrifos toxicity by 2.5-fold but did not affect the toxicity of chlorpyrifos-oxon. Exposure to alachlor and chlorpyrifos did not affect AChE compared to chlorpyrifos alone. However, exposure to chlorpyrifos-oxon and alachlor significantly increased acetylcholinesterase (AChE) activity by 1.4-fold. GST activity, but not P450 or general esterases, was significantly increased in bees exposed to alachlor. These data provide evidence that triazine and chloroacetanilide herbicide exposure alters detoxification enzyme activity and, in turn, alters the sensitivity of bees to organophosphorothioate insecticides. Importantly, these data can be used to guide future studies aiming to test safety profiles for pollinators and expand regulatory framework required for pesticide registration.


Assuntos
Atrazina , Clorpirifos , Inseticidas , Abelhas , Animais , Atrazina/toxicidade , Clorpirifos/toxicidade , Acetilcolinesterase , Inseticidas/toxicidade , Triazinas , Esterases
15.
J Int Med Res ; 50(11): 3000605221133988, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-36418928

RESUMO

Lamotrigine is an antiepileptic drug that can be used to control many types of seizures as a single-agent or an add-on therapy in patients over 2 years of age. In addition to common adverse reactions, this current case report describes a paediatric male patient with a rare side-effect of persistent penile erectile due to lamotrigine. Previous studies have shown that it can improve sexual function in adult male patients. This patient suffered from refractory epilepsy and pneumonia. He had taken a variety of antiepileptic drugs for a long time and developed priapism after the dosage of lamotrigine had been increased. The priapism improved after drug withdrawal and sedation. Further research is needed to elucidate the mechanism of this rare side-effect.


Assuntos
Efeitos Colaterais e Reações Adversas Relacionados a Medicamentos , Epilepsia , Priapismo , Adulto , Humanos , Masculino , Criança , Lamotrigina/efeitos adversos , Anticonvulsivantes/efeitos adversos , Priapismo/induzido quimicamente , Priapismo/tratamento farmacológico , Epilepsia/tratamento farmacológico , Triazinas/efeitos adversos
16.
Inorg Chem ; 61(48): 19475-19482, 2022 Dec 05.
Artigo em Inglês | MEDLINE | ID: mdl-36414025

RESUMO

Bearing triazine-centered linkers, three primitive metal-organic frameworks (MOFs) with a Zr6O4 cluster have been prepared as ZrL1 (without any branch), ZrL2 (with -F), and ZrL3 (with -SCH3). The electrocatalytic hydrogen evolution reaction (HER) by their pristine and transition metal-loaded (TM-loaded) forms was studied. It was found that the loading of TM ions could enhance the electrocatalytic power of these TM-loaded MOFs in HER, as reflected by their lower overpotentials and smaller Tafel slopes when compared with primitive MOFs. More importantly, the best electrocatalytic HER performance of ZrL3-TM among all TM-loaded MOFs studied in this work highlights the effective housing of TM ions for unambiguous active sites through cooperative coordination by triazinic N and thioether pendants. This work proposes microenvironment regulation of MOFs as an effective strategy to enhance the electrocatalytic activity of MOF materials.


Assuntos
Estruturas Metalorgânicas , Elementos de Transição , Hidrogênio , Íons , Triazinas
17.
Int J Mol Sci ; 23(22)2022 Nov 10.
Artigo em Inglês | MEDLINE | ID: mdl-36430300

RESUMO

Methods for the synthesis of two types of isomeric dispirocompounds based on imidazothiazolotriazine and pyrrolidineoxindole, differing in the structure of imidazothiazolotriazine fragment, namely, linear dispiro[imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazine-6,3'-pyrrolidine- 4',3″-indolines] and angular dispiro[imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine-7,3'-pyrrolidine-4',3″-indolines] were proposed. The first method relies on a 1,3-dipolar cycloaddition of azomethine ylides generated in situ from paraformaldehyde and N-alkylglycine derivatives to the corresponding oxindolylidene derivatives of imidazothiazolotriazine. The cycloaddition leads to a mixture of two diastereomers resulted from anti- and syn-approaches of azomethine ylide in approximately a 1:1 ratio, which were separated by column chromatography. Another method consists in rearrangement of linear dispiro[imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazine-6,3'-pyrrolidine-4',3″-indolines] into hitherto unavailable angular dispiro[imidazo[4,5-e]thiazolo[2,3-c]-[1,2,4]triazine-7,3'-pyrrolidine-4',3″-indolines] upon treatment with KOH. It was found that the anti-diastereomer of linear type underwent rearrangement into the isomeric angular syn-diastereomer, while the rearrangement of the linear syn-diastereomer gave the angular anti-diastereomer.


Assuntos
Compostos de Espiro , Tiossemicarbazonas , Compostos de Espiro/química , Tiossemicarbazonas/química , Pirrolidinas/química , Triazinas
18.
Molecules ; 27(22)2022 Nov 12.
Artigo em Inglês | MEDLINE | ID: mdl-36431902

RESUMO

C-glycopyranosyl derivatives of six-membered heterocycles are scarcely represented in the chemical literature and the title 3-glycopyranosyl-1,2,4-triazines are completely unknown. In this paper, the first synthesis of this compound class is accomplished by the cyclocondensation of C-glycosyl formamidrazones and 1,2-dicarbonyl derivatives. In addition, the synthesis of C-glycopyranosyl 1,2,4-triazin-5(4H)-ones was also carried out by the transformation of the above formamidrazones with α-keto-carboxylic esters. Inverse electron demand Diels-Alder reactions of 3-glycopyranosyl-1,2,4-triazines with a bicyclononyne derivative yielded the corresponding annulated 2-glycopyranosyl pyridines.


Assuntos
Elétrons , Triazinas , Reação de Cicloadição , Triazinas/química , Ciclização , Piridinas/química
19.
Bioorg Med Chem Lett ; 77: 129042, 2022 12 01.
Artigo em Inglês | MEDLINE | ID: mdl-36332884

RESUMO

Triazine-linked triazole compounds (4a-j) were designed, synthesized, and then examined for their anticonvulsant abilities. Compounds 4e, 4f, 4g, 4i, and 4j displayed significant anticonvulsant activity in both maximum electroshock seizure (MES) and pentylenetetrazole (PTZ) induced seizure during the preliminary screening. The phase II anticonvulsant activity statistics revealed that compounds 4e, 4f, 4g, 4i, and 4j demonstrated excellent activity as compared to the conventional drugs methaqualone and valproate, supporting the potential of these triazine-linked triazole analogues as novel anticonvulsant agents. To take use of the findings, computational parameters including docking analysis and drug-likeness prediction were carried out. Molecular modelling studies supported the essential pharmacophoric information that the structure activity relationship offered. The triazine-linked triazole analogues that were investigated might be viewed as helpful models for future research and derivatization.


Assuntos
Anticonvulsivantes , Triazinas , Humanos , Anticonvulsivantes/farmacologia , Anticonvulsivantes/uso terapêutico , Anticonvulsivantes/química , Simulação de Acoplamento Molecular , Triazinas/farmacologia , Pentilenotetrazol , Convulsões/induzido quimicamente , Convulsões/tratamento farmacológico , Eletrochoque , Triazóis , Relação Estrutura-Atividade , Estrutura Molecular
20.
Molecules ; 27(21)2022 Oct 22.
Artigo em Inglês | MEDLINE | ID: mdl-36363982

RESUMO

A series of copper(II) complexes of 2-imino-2H-chromen-3-yl-1,3,5-triazines 2a-h, 3-(benzoxazol-2-yl)-2H-chromen-2-imines 4a-b, and 3-(benzothiazol-2-yl)-2H-chromen-2-imines 6a-c were obtained by reacting of appropriate 2-iminocoumarin ligands L1a-h, L3a-b, and L5a-c with 3-fold molar excess of copper(II) chloride. The structure of these compounds was confirmed by IR spectroscopy, elemental analysis, and single-crystal X-ray diffraction data (2f, 2g, 2h, and 6c). All the synthesized complexes were screened for their activity against five human cancer cell lines: DAN-G, A-427, LCLC-103H, SISO, and RT-4 by using a crystal violet microtiter plate assay and relationships between structure and in vitro cytotoxic activity are discussed. The coordination of 2-iminocoumarins with copper(II) ions resulted in complexes 2a-h, 4a-b, and 6a-c with significant inhibitory properties toward tested tumor cell lines with IC50 values ranging from 0.04 µM to 15.66 µM. In comparison to the free ligands L1a-h, L3a-b, and L5a-c, the newly prepared Cu(II) complexes often displayed increased activity. In the series of copper(II) complexes of 2-imino-2H-chromen-3-yl-1,3,5-triazines 2a-h the most potent compound 2g contained a 4-phenylpiperazine moiety at position 6 of the 1,3,5-triazine ring and an electron-donating diethylamino group at position 7' of the 2-iminocoumarin scaffold. Among the Cu(II) complexes of 3-(benzoxazol-2-yl)-2H-chromen-2-imines 4a-b and 3-(benzothiazol-2-yl)-2H-chromen-2-imines 6a-c the most active was benzoxazole-2-iminocoumarin 4b that also possessed a diethylamino group at position 7' of the 2-iminocoumarin moiety. Moreover, compound 4b was found to be the most prominent agent and displayed the higher potency than cisplatin against tested cell lines.


Assuntos
Antineoplásicos , Complexos de Coordenação , Humanos , Cobre/química , Benzoxazóis/farmacologia , Triazinas , Antineoplásicos/química , Linhagem Celular Tumoral , Benzotiazóis , Cristalografia por Raios X , Ligantes , Iminas , Complexos de Coordenação/química
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