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1.
RSC Adv ; 14(8): 5264-5275, 2024 Feb 07.
Artigo em Inglês | MEDLINE | ID: mdl-38343997

RESUMO

Epoxy resin has been extensively used in many industrial and daily applications due to its unique properties. However, the high flammability of epoxy has limited its further development. DOPO derivatives, which are organophosphorus compounds, are highly effective components of flame retardant epoxy composites due to their good compatibility with the resin and their lower toxicity compared to halogenated compounds. This study synthesized sixteen new DOPO derivatives, characterizing their chemical structures with NMR spectroscopy. The combination of synthesized DOPO derivatives and APP-PEI (ammonium polyphosphate-polyethyleneimine) has shown a synergistic effect on enhancing the flame retardancy of epoxy resin with the UL-94 V-0 rating and the LOI value of 28.6%. Moreover, the epoxy composites displayed relatively high mechanical performance with the impact strength of 26-28 kJ m-2.

2.
Chem Biodivers ; 20(9): e202301037, 2023 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-37529975

RESUMO

Four undescribed phenolic glycosides including three stilbene derivatives (1 and 3) and sodium salt of 3 (2), and a chalcone glycoside (4), together with thirteen known compounds (5-17) were isolated from the leaves of Syzygium attopeuense (Gagnep.) Merr. & L.M.Perry. Their chemical structures were elucidated to be (Z)-gaylussacin (1), 6''-O-galloylgaylussacin sodium salt (2), 6''-O-galloylgaylussacin (3), 4'-O-[ß-D-glucopyranosyl-(1→6)-glucopyranosyl]oxy-2'-hydroxy-6'-methoxydihydrochalcone (4), gaylussacin (5), pinosilvin 3-O-ß-D-glucopyranoside (6), myricetin-3-O-(2''-O-galloyl)-α-L-rhamnopyranoside (7), myricetin-3-O-(3''-O-galloyl)-α-L-rhamnopyranoside (8), myricetin-3-O-α-L-rhamnopyranoside (9), quercitrin (10), myricetin-3-O-ß-D-glucopyranoside (11), myricetin-3-O-ß-D-galactopyranoside (12), quercetin 3-O-α-L-arabinopyranoside (13), myricetin-3-O-2''-O-galloyl)-α-L-arabinopyranoside (14), (+)-gallocatechin (15), (-)-epigallocatechin (16), and 3,3',4'-trimethoxyellagic acid 4-O-ß-D-glucopyranoside (17) by the analysis of HR-ESI-MS, 1D and 2D NMR spectra in comparison with the previously reported data. Compounds 1-3, 5, and 6 significant inhibition of NO production in LPS-activated RAW264.7 cells, with IC50 values ranging from 18.37±1.38 to 35.12±2.53 µM, compared to a positive control (dexamethasone) with an IC50 value of 15.37±1.42 µM.


Assuntos
Glicosídeos , Syzygium , Glicosídeos/farmacologia , Glicosídeos/química , Óxido Nítrico , Fenóis/farmacologia , Sódio , Estrutura Molecular
3.
J Nat Med ; 77(4): 964-971, 2023 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-37358723

RESUMO

Three undescribed triterpene glycosides syzybullosides A-C (1-3) along with fourteen known compounds were isolated from the leaves of Syzygium bullockii (Hance) Merr.& L.M. Perry, including six triterpene glycosides (1-6), four phenolics (7-9, 17), four megastigmanes (10-13), and three flavonoids (14-16). The structures of 1-17 were elucidated by extensive spectroscopic analysis, including IR, HR-ESI-MS, 1D and 2D NMR spectra. Compounds 1-10 and 12-17 inhibited nitric oxide (NO) production in lipopolysaccharide activated RAW264.7 cells with IC50 values ranging from 1.30 to 13.70 µM, lower than that of the positive control compound, L-NMMA (IC50 = 33.8 µM).


Assuntos
Syzygium , Triterpenos , Estrutura Molecular , Óxido Nítrico , Glicosídeos/farmacologia , Glicosídeos/química , Triterpenos/farmacologia , Triterpenos/química
4.
Chem Biodivers ; 20(3): e202201048, 2023 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-36879412

RESUMO

A new isopropyl chromone (1) and a new flavanone glucoside (2) together with eleven known compounds (3-13) were isolated from the leaves of Syzygium cerasiforme (Blume) Merr. & L.M.Perry. Their structures were elucidated as 5,7-dihydroxy-2-isopropyl-6,8-dimethyl-4H-chromen-4-one (1), 5,7-dihydroxyflavanone 7-O-ß-D-(6''-O-galloylglucopyranoside) (2), strobopinin (3), demethoxymatteucinol (4), pinocembrin-7-O-ß-D-glucopyranoside (5), (2S)-hydroxynaringenin-7-O-ß-D-glucopyranoside (6), afzelin (7), quercetin (8), kaplanin (9), endoperoxide G3 (10), grasshopper (11), vomifoliol (12), litseagermacrane (13) by the analysis of HR-ESI-MS, NMR, and CD spectral data. Compounds 1, 2, 5, 6 and 10 inhibited NO production on LPS-activated RAW264.7 cells with IC50 values of 12.28±1.15, 8.52±1.62, 7.68±0.87, 9.67±0.57, and 6.69±0.34 µM, respectively, while the IC50 values of the other compounds ranging from 33.38±0.78 to 86.51±2.98 µM, compared to that of the positive control, NG -monomethyl-L-arginine acetate (L-NMMA) with an IC50 value of 32.50±1.00 µM.


Assuntos
Flavanonas , Syzygium , Cromonas/farmacologia , Flavanonas/farmacologia , Glucosídeos/farmacologia , Glucosídeos/química , Estrutura Molecular , Óxido Nítrico , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Syzygium/química
5.
Vet Res Commun ; 47(3): 1773-1776, 2023 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-36823481

RESUMO

African swine fever virus (ASFV) causes African swine fever (ASF), a deadly disease affecting both domestic pigs and wild boars. ASF has become endemic in Vietnam since its first appearance in early 2019. Our previous molecular surveillance studies revealed that all the ASFV strains circulating in Vietnam belong to p72 genotype II, p54 genotype II, CD2v serogroup 8, and CVR of B602L gene variant type I. However, the genetic analysis based on the tandem repeat sequences located between I73R and I329L genes revealed three different intergenic region (IGR) variants; I, II, and III. In this study, using ASFV field isolates collected from September 24th to December 27th, 2021, we report, for the first time, novel IGR IV variants circulating in the Vietnamese pig population.


Assuntos
Vírus da Febre Suína Africana , Febre Suína Africana , Doenças dos Suínos , Suínos , Animais , Sus scrofa , Vírus da Febre Suína Africana/genética , Febre Suína Africana/epidemiologia , Febre Suína Africana/genética , DNA Intergênico/genética , Vietnã/epidemiologia , Surtos de Doenças , Filogenia , Genótipo , Doenças dos Suínos/epidemiologia
6.
Sci Total Environ ; 862: 160802, 2023 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-36493814

RESUMO

In this study, the operation parameters of a partial nitrification process (PN) treating saline wastewater were optimized using the Box-Behnken design via the response surface methodology (BBD-RSM). A novel strategy based on the control of the carbon/nitrogen ratio (C/N), alkalinity/ammonia ratio (K/A), and salinity in three stages was used to achieve PN in a sequence batch reactor. The results demonstrated that a high and stable PN was completed after 50 d with an ammonia removal efficiency (ARE) of 98.37 % and nitrite accumulation rate (NAR) of 85.93 %. Next, BBD-RSM was applied, where ARE and NAR were the responses. The highest responses from the confirmation experiment were 99.9 % ± 0.04 and 95.25 % ± 0.32 when the optimum C/N, K/A, and salinity were identified as 0.84, 2, and 5.5 (g/L), respectively. The results were higher than those for the nonoptimized reactor. The developed regression model adequately forecasts the PN performance under optimal conditions. Therefore, this study provides a promising strategy for controlling the PN process and shows how the BBD-RSM model can improve the PN performance.


Assuntos
Nitrificação , Águas Residuárias , Amônia , Salinidade , Reatores Biológicos , Nitrogênio , Nitritos , Carbono , Oxirredução , Esgotos , Desnitrificação
7.
Nat Prod Res ; 37(2): 305-312, 2023 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34498962

RESUMO

A new muurolane-type sesquiterpene, a new flavone arabinofuranoside derivative, and other five known flavone arabinofuranoside derivatives were isolated from the leaves of Fissistigma bicolor (Annonaceae family). Their chemical structures were determined to be (1S,6R,7S)-muurola-4,10(14)-diene-15-ol (1), quercetin 3-O-ß-D-apiofuranosyl-(1→2)-α-L-arabinofuranoside (2), quercetin 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinofuranoside (3), quercetin 3-O-α-L-arabinofuranoside (4), kaempferol 3-O-ß-D-apiofuranosyl-(1→2)-α-L-arabinofuranoside (5), kaempferol 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinofuranoside (6), and kaempferol 3-O-α-L-arabinofuranoside (7) by analyses of HR-ESI-MS and NMR spectral data. Compounds 4 and 7 containing monosaccharide, arabinofuranoside, potentially inhibited NO productions in LPS activated RAW264.7 cells (IC50 13.4 ± 0.5 and 12.6 ± 0.4 µM) in compared to disaccharide derivatives (IC50 ranging from 58.9 ± 3.3 to 65.6 ± 3.8 µM).


Assuntos
Annonaceae , Flavonas , Quempferóis/análise , Quercetina , Annonaceae/química , Flavonas/farmacologia , Flavonas/análise , Glicosídeos/química , Folhas de Planta/química , Estrutura Molecular
8.
Nat Prod Res ; 36(6): 1616-1620, 2022 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-33615920

RESUMO

New propene derivative 1-(3',4'-methylenedioxyphenyl)-2-(2''-hydroxy-5-(3'''-hydroxypropyl)-3''-methoxyphenyl)prop-2-en-1-one (1), along with three known triterpenoids ursolic acid (2), pomolic acid (3), and maslinic acid (4) were isolated from the leaves of Styrax annamensis species. All structures were assigned by spectroscopic analysis. Compound 1 showed potent cytotoxicity against four cancer cell lines (KB, HepG2, Lu, and MCF7) with the IC50 values of 3.19, 2.87, 2.33, and 2.44 µM, respectively.


Assuntos
Styrax , Triterpenos , Estrutura Molecular , Folhas de Planta/química , Styrax/química , Triterpenos/química
9.
Mol Divers ; 26(1): 229-243, 2022 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-33765238

RESUMO

Searching for bioactive agents from medicinal plants, eleven constituents were isolated from Polyscias guilfoylei stem for the first time, including a nucleoside uracil (1), two sterols ß-sitosterol (2) and daucosterol (3), a saponin androseptoside A (4), two lignans (+)-pinoresinol (5) and (+)-syringaresinol (6), four phenolic acids protocatechuic acid (7), methyl protocatechuate (8), caffeic acid (9), and 5-O-caffeoylquinic acid (10), and a flavonoid quercitrin (11). Metabolites 1, 4, and 6-11 have never been observed in genus Polyscias before. Phenolic compounds 7 and 9 possessed the respective IC50 values of 21.33 and 13.88 µg/mL in DPPH (2,2-diphenyl-1-picrylhydrazyl) antioxidative assay, as compared with that of the positive control resveratrol (IC50 = 13.21 µg/mL). From density functional theory (DFT) calculated approach, the DPPH free radical scavenging capacity of two compounds 7 and 9 can be explained by the role of OH groups at carbons C-3 and C-4. Antioxidative actions of these two potential agents are followed HAT (H atom transfer) mechanism by OH bond disruption in gas, but SPLET (sequential proton loss electron transfer) mechanism in solvents water and methanol. Compared to 4-OH group, 3-OH group showed better bond disruption enthalpies and better kinetic energies since it reacted with HOO• and DPPH radicals. Sterols 2-3 and flavonoid 11 induced the IC50 values of < 2.0 µg/mL better than the positive control acarbose (IC50 = 184.0 µg/mL) in α-glucosidase inhibitory assay. Their interactions with human intestinal C- and N-terminal domains of α-glucosidase were explored using molecular docking study. The obtained results proved that compounds 2, 3, and 11 bind relatively stronger with the C-terminal domain than to the N-terminal domain through pivotal residues in the binding site and could be hypothesized as mixed inhibitors.


Assuntos
Araliaceae , alfa-Glucosidases , Antioxidantes/química , Antioxidantes/farmacologia , Araliaceae/metabolismo , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Humanos , Simulação de Acoplamento Molecular , alfa-Glucosidases/metabolismo
10.
Prog Chem Org Nat Prod ; 116: 135-209, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34698947

RESUMO

Herbaceous annual plants of the genus Xanthium are widely distributed throughout the world and have been employed medicinally for millennia. This contribution aims to provide a systematic overview of the diverse structural classes of Xanthium secondary metabolites, as well as their pharmacological potential. On searching in various reference databases with a combination of three keywords "Xanthium", "Phytochemistry", and "Pharmacology", relevant publications have been obtained subsequently. From the 1950s to the present, phytochemical investigations have focused mainly on 15 Xanthium species, from which 300 compounds have been isolated and structurally resolved, primarily using NMR spectroscopic methodology. Xanthium constituents represent several secondary metabolite types, including simple phenols, sulfur and nitrogen-containing compounds, lignans, sterols, flavonoids, quinones, coumarins, and fatty acids, with terpenoids being the most common of these. Among the 174 terpenoids characterized, xanthanolide sesquiterpenoids are abundant, and most of the compounds isolated containing sulfur were found to be new in Nature. The ethnomedical uses of Xanthium crude extracts are supported by the in vitro and in vivo effects of their constituents, such as cytotoxicity, antioxidant, antibacterial, antifungal, antidiabetes, and hepatoprotective activities. Toxicological results suggest that Xanthium plant extracts are generally safe for use. In the future, additional phytochemical investigations, along with further assessments of the biological profiles and mechanism of action studies of the components of Xanthium species, are to be expected.


Assuntos
Plantas Medicinais , Xanthium , Medicina Tradicional , Compostos Fitoquímicos/farmacologia , Extratos Vegetais
11.
Chem Biodivers ; 18(11): e2100396, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34529335

RESUMO

A new racemic xanthone, garmckeanin A (1), and eight known analogs 2-9 were isolated from the ethyl acetate (AcOEt) extract of the Vietnamese Garcinia mckeaniana leaves. Their structures were determined by MS and NMR spectral analyses and compared with the literature. The AcOEt extract showed good cytotoxicity against cancer cell lines KB, Lu, Hep-G2 and MCF7, with IC50 values of 5.40-8.76 µg/mL, and it also possessed α-glucosidase inhibitory activity, with an IC50 value of 9.17 µg/mL. Garmckeanin A (1) exhibited inhibition of all cancer cell lines, with an IC50 value of 7.3-0.9 µM. Allanxanthone C (5) successfully controlled KB growth, with an IC50 value of 0.54 µM, higher than that of the positive control, ellipticine (IC50 1.22 µM). Norathyriol (8) was a promising α-glucosidase inhibitor, with an IC50 value of 0.07 µM, much higher than that of the positive control, acarbose (IC50 161.0 µM). The interactions of the potential α-glucosidase inhibitors with the C- and N-terminal domains of human intestinal α-glucosidase were also investigated by molecular docking study. The results indicated that bannaxanthone D (2), garcinone E (4), bannaxanthone E (6), and norathyriol (8) exhibit higher binding affinity to the C-terminal than to the N-terminal domain through essential residues in the active sites. In particular, compound 8 could be assumed to be the most potent mixed inhibitor.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Garcinia/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Simulação de Acoplamento Molecular , Xantonas/farmacologia , alfa-Glucosidases/metabolismo , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Humanos , Estrutura Molecular , Células Tumorais Cultivadas , Xantonas/química , Xantonas/isolamento & purificação
12.
Carbohydr Polym ; 257: 117593, 2021 Apr 01.
Artigo em Inglês | MEDLINE | ID: mdl-33541634

RESUMO

In this work, we treated chitin with 2-(azidomethyl)oxirane and successfully involved the resultant azido chitin derivatives in the ultrasound-assisted Cu(I)-catalyzed azido-alkyne click (CuAAC) reaction with propargylic ester of N,N,N-trimethyl glycine. Thus, we obtained novel water-soluble triazole chitin derivatives. The triazole chitin derivatives and their nanoparticles are characterized by a high in vitro antibacterial activity, which is the same or even higher than that of commercial antibiotics ampicillin and gentamicin. The obtained derivatives are non-toxic. Moreover, the obtained water-soluble polymers are highly efficient green catalysts for the aldol reaction in green solvent water. The catalysts can be easily extracted from the reaction mixture by its precipitation with green solvent ethanol followed by centrifugation and they can be reused at least 10 times.


Assuntos
Antibacterianos/química , Quitosana/síntese química , Quitosana/farmacologia , Óxido de Etileno/química , Nanopartículas/química , Triazóis/química , Aldeídos/química , Ampicilina/química , Exoesqueleto , Animais , Anti-Infecciosos , Catálise , Química Click , Ésteres , Gentamicinas/química , Química Verde , Íons , Espectroscopia de Ressonância Magnética , Solubilidade , Solventes , Viscosidade
13.
Food Chem ; 343: 128676, 2021 May 01.
Artigo em Inglês | MEDLINE | ID: mdl-33250292

RESUMO

We used nanoparticles which possess simultaneously active (antimicrobial, UV-protective and antioxidant) and smart (temperature sensing) properties. The nanoparticles (2Rh = 450 nm, PDI = 0.118 ± 0.014, ζ-potential = 21 mV and Tg = 8 ± 1 °C) are based on polyethylene glycol (PEG)/methyl cellulose (MC) core with anthocyanidin and sodium acetate, and chitosan/gallotannin-based shell. The core of nanoparticles acts as a temperature indicator, changing its color from colorless into deep purple at 8 °C, while the shell provides antimicrobial (due to chitosan), UV-protective and antioxidant (due to gallotannin) effects. We incorporated these nanoparticles into the chitosan matrix. The coatings demonstrated improved mechanical and barrier properties compared with the pure chitosan coating. The elaborated coatings pronouncedly improve the shelf-life of Ricotta cheese. Moreover, they serve as thermo indicators, which warn about cheese storage at an unacceptable temperature. Thus, we developed new coatings in which all properties are enabled by a single type of nanoparticles.


Assuntos
Anti-Infecciosos/química , Quitosana/química , Embalagem de Alimentos/métodos , Nanopartículas/química , Anti-Infecciosos/farmacologia , Antioxidantes/química , Queijo/análise , Escherichia coli/efeitos dos fármacos , Fungos/efeitos dos fármacos , Taninos Hidrolisáveis/química , Metilcelulose/química , Nanopartículas/toxicidade , Polietilenoglicóis/química , Staphylococcus aureus/efeitos dos fármacos , Temperatura , Resistência à Tração
14.
SAGE Open Med Case Rep ; 8: 2050313X20981464, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-33489233

RESUMO

Acute obstructive hydrocephalus is a complication of intraventricular hemorrhage, which requires a combination of medical and surgical treatments. We report a clinical case of intraventricular hemorrhage extension secondary to a ruptured arteriovenous malformation, successfully treated with a combination of methods: endovascular embolization of arteriovenous malformation, external ventricular drainage, intraventricular fibrinolysis with low-dose recombinant tissue plasminogen activator, and medical treatment with the neurotrophic drug Cerebrolysin in combination with neurorehabilitation.

15.
Folia Parasitol (Praha) ; 662019 Aug 19.
Artigo em Inglês | MEDLINE | ID: mdl-31490126

RESUMO

Gnathostomes are of interest because of their unique appearance and medical importance. Among 13 valid species of the genus Gnathostoma Owen, 1836 (Nematoda: Spirurida), two species, G. doloresi Tubangui, 1925 and G. hispidum Fedtschenko, 1872, are parasites of pigs but their larvae can infect humans to cause gnathostomiasis. In this study, we collected adults of Gnathostoma sp. from the stomach of domestic pigs (Sus scrofa domesticus Linnaeus) from Dien Bien Province, northern Vietnam. Morphologically, nematodes found here are most similar to G. doloresi with a slight difference in the spicules of males. In contrast, they are genetically distinct from G. doloresi and other species of Gnathostoma in both ITS2 and cox1 sequences. The findings of the present study suggest that specimens of Gnathostoma sp. found in Dien Bien are likely a new species and emphasise the need of further studies on the taxonomy and phylogenetic relationship of species of Gnathostoma. Special attention should also be paid to swine and human gnathostomiasis in Dien Bien Province, Vietnam and the neighbouring areas of China and Laos.


Assuntos
Gnathostoma/anatomia & histologia , Gnathostoma/genética , Gnatostomíase/veterinária , Doenças dos Suínos/parasitologia , Animais , DNA Espaçador Ribossômico/análise , Complexo IV da Cadeia de Transporte de Elétrons/análise , Feminino , Gnatostomíase/parasitologia , Proteínas de Helminto/análise , Masculino , Filogenia , Sus scrofa , Suínos , Vietnã
16.
Emerg Infect Dis ; 25(7): 1433-1435, 2019 07.
Artigo em Inglês | MEDLINE | ID: mdl-31075078

RESUMO

African swine fever is one of the most dangerous diseases of swine. We confirmed the 2019 outbreak in Vietnam by real-time reverse transcription PCR. The causative strain belonged to p72 genotype II and was 100% identical with viruses isolated in China (2018) and Georgia (2007). International prevention and control collaboration is needed.


Assuntos
Febre Suína Africana/epidemiologia , Febre Suína Africana/história , Febre Suína Africana/virologia , Animais , Asfarviridae/classificação , Asfarviridae/genética , DNA Viral , Surtos de Doenças , Genes Virais , Genótipo , Sequenciamento de Nucleotídeos em Larga Escala , História do Século XXI , Filogenia , Análise de Sequência de DNA , Suínos
17.
Nat Prod Commun ; 11(12): 1789-1792, 2016 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-30508334

RESUMO

Dihydroartemisinin was converted to its corresponding alkyne-functionalized esters, which were subsequently deployed as substrates for a 'click' chemistry-mediated coupling-with 3'-azido-3'-deoxythydimine (AZT) to furnish novel triazole-artesunate-AZT hybrid compounds. Moreover, various substituted triazole-artemisinin :hybrids were synthesized based on 'click' chemistry between propargyl-substituted derivatives and artemisinin containing a 2-hydroxypropane unit. Fourteen new hybrids were thus successfully prepared and evaluated as cytotoxic agents, revealing an interesting anticancer activity of four triazole-artemisinin derivative hybrids in KB and HepG2 cancer cell lines.


Assuntos
Antineoplásicos , Artemisininas , Triazóis , Zidovudina , Antineoplásicos/química , Antineoplásicos/farmacologia , Artemisininas/química , Artemisininas/farmacologia , Sobrevivência Celular/efeitos dos fármacos , Química Click , Células Hep G2 , Humanos , Células KB , Triazóis/química , Triazóis/farmacologia , Zidovudina/química , Zidovudina/farmacologia
18.
Bioorg Med Chem Lett ; 24(10): 2244-6, 2014 May 15.
Artigo em Inglês | MEDLINE | ID: mdl-24745968

RESUMO

In this Letter, we report a convenient and efficient method for the synthesis of new simplified derivatives of hemiasterlin in which the α,α-dimethylbenzylic moiety A is replaced by α,ß-unsaturated aryl groups as Michael acceptor. Most of these derivatives have a strong cytotoxic activity on three human tumor cell lines (KB, Hep-G2 and MCF7). Analogs 17b and 17f showed a high cytotoxicity against KB and Hep-G2 cancer cell lines comparable to paclitaxel and ellipticine.


Assuntos
Oligopeptídeos/síntese química , Ensaios de Seleção de Medicamentos Antitumorais , Células Hep G2 , Humanos , Células KB , Células MCF-7 , Oligopeptídeos/química , Oligopeptídeos/farmacologia , Relação Estrutura-Atividade
19.
Chemistry ; 19(19): 5966-71, 2013 May 03.
Artigo em Inglês | MEDLINE | ID: mdl-23512331

RESUMO

A five-step procedure for the synthesis of cis-1-tosyl-2-tosyloxymethyl-3-(trifluoromethyl)aziridine was developed, starting from 1-ethoxy-2,2,2-trifluoroethanol, involving imination, aziridination, ester reduction, hydrogenation, and N-,O-ditosylation steps. Further synthetic elaborations revealed a remarkable difference in the reactivity of cis-1-tosyl-2-tosyloxymethyl-3-(trifluoromethyl)aziridine with respect to aromatic sulfur and oxygen nucleophiles, thus enabling the selective deployment of this versatile substrate as a building block for the synthesis of functionalized aziridines, azetidines, and benzo-fused dithianes, oxathianes, dioxanes, and (thio)morpholines.


Assuntos
Azetidinas/síntese química , Aziridinas/síntese química , Dioxanos/síntese química , Compostos Heterocíclicos/química , Hidrocarbonetos Fluorados/química , Hidrocarbonetos Fluorados/síntese química , Morfolinas/síntese química , Oxigênio/química , Quinolizinas/síntese química , Compostos de Enxofre/síntese química , Enxofre/química , Trifluoretanol/análogos & derivados , Trifluoretanol/química , Azetidinas/química , Aziridinas/química , Dioxanos/química , Morfolinas/química , Quinolizinas/química , Estereoisomerismo , Compostos de Enxofre/química
20.
Bioorg Med Chem Lett ; 15(10): 2629-31, 2005 May 16.
Artigo em Inglês | MEDLINE | ID: mdl-15863331

RESUMO

The synthesis of novel 10-deoxoartemisinin derivatives containing heterocyclic rings and hydrophilic groups, and their antimalarial activity assessment are described. Most of the synthesized derivatives are more potent than artemisinin, especially, some of them are 20-25 times more potent than artemisinin to two chloroquine-resistant and sensitive clones of P. falciparum.


Assuntos
Antimaláricos/síntese química , Artemisininas/síntese química , Animais , Antimaláricos/farmacologia , Artemisininas/farmacologia , Plasmodium falciparum/efeitos dos fármacos
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