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1.
RSC Adv ; 14(8): 5264-5275, 2024 Feb 07.
Artículo en Inglés | MEDLINE | ID: mdl-38343997

RESUMEN

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.
Artículo en Inglés | MEDLINE | ID: mdl-37529975

RESUMEN

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.


Asunto(s)
Glicósidos , Syzygium , Glicósidos/farmacología , Glicósidos/química , Óxido Nítrico , Fenoles/farmacología , Sodio , Estructura Molecular
3.
J Nat Med ; 77(4): 964-971, 2023 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-37358723

RESUMEN

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).


Asunto(s)
Syzygium , Triterpenos , Estructura Molecular , Óxido Nítrico , Glicósidos/farmacología , Glicósidos/química , Triterpenos/farmacología , Triterpenos/química
4.
Chem Biodivers ; 20(3): e202201048, 2023 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-36879412

RESUMEN

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.


Asunto(s)
Flavanonas , Syzygium , Cromonas/farmacología , Flavanonas/farmacología , Glucósidos/farmacología , Glucósidos/química , Estructura Molecular , Óxido Nítrico , Extractos Vegetales/farmacología , Extractos Vegetales/química , Syzygium/química
5.
Vet Res Commun ; 47(3): 1773-1776, 2023 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-36823481

RESUMEN

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.


Asunto(s)
Virus de la Fiebre Porcina Africana , Fiebre Porcina Africana , Enfermedades de los Porcinos , Porcinos , Animales , Sus scrofa , Virus de la Fiebre Porcina Africana/genética , Fiebre Porcina Africana/epidemiología , Fiebre Porcina Africana/genética , ADN Intergénico/genética , Vietnam/epidemiología , Brotes de Enfermedades , Filogenia , Genotipo , Enfermedades de los Porcinos/epidemiología
6.
Sci Total Environ ; 862: 160802, 2023 Mar 01.
Artículo en Inglés | MEDLINE | ID: mdl-36493814

RESUMEN

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.


Asunto(s)
Nitrificación , Aguas Residuales , Amoníaco , Salinidad , Reactores Biológicos , Nitrógeno , Nitritos , Carbono , Oxidación-Reducción , Aguas del Alcantarillado , Desnitrificación
7.
Nat Prod Res ; 37(2): 305-312, 2023 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-34498962

RESUMEN

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).


Asunto(s)
Annonaceae , Flavonas , Quempferoles/análisis , Quercetina , Annonaceae/química , Flavonas/farmacología , Flavonas/análisis , Glicósidos/química , Hojas de la Planta/química , Estructura Molecular
8.
Nat Prod Res ; 36(6): 1616-1620, 2022 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-33615920

RESUMEN

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.


Asunto(s)
Styrax , Triterpenos , Estructura Molecular , Hojas de la Planta/química , Styrax/química , Triterpenos/química
9.
Mol Divers ; 26(1): 229-243, 2022 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-33765238

RESUMEN

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.


Asunto(s)
Araliaceae , alfa-Glucosidasas , Antioxidantes/química , Antioxidantes/farmacología , Araliaceae/metabolismo , Inhibidores de Glicósido Hidrolasas/química , Inhibidores de Glicósido Hidrolasas/farmacología , Humanos , Simulación del Acoplamiento Molecular , alfa-Glucosidasas/metabolismo
10.
Prog Chem Org Nat Prod ; 116: 135-209, 2021.
Artículo en Inglés | MEDLINE | ID: mdl-34698947

RESUMEN

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.


Asunto(s)
Plantas Medicinales , Xanthium , Medicina Tradicional , Fitoquímicos/farmacología , Extractos Vegetales
11.
Chem Biodivers ; 18(11): e2100396, 2021 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-34529335

RESUMEN

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.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Garcinia/química , Inhibidores de Glicósido Hidrolasas/farmacología , Simulación del Acoplamiento Molecular , Xantonas/farmacología , alfa-Glucosidasas/metabolismo , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Proliferación Celular/efectos de los fármacos , Ensayos de Selección de Medicamentos Antitumorales , Inhibidores de Glicósido Hidrolasas/química , Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Humanos , Estructura Molecular , Células Tumorales Cultivadas , Xantonas/química , Xantonas/aislamiento & purificación
12.
Carbohydr Polym ; 257: 117593, 2021 Apr 01.
Artículo en Inglés | MEDLINE | ID: mdl-33541634

RESUMEN

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.


Asunto(s)
Antibacterianos/química , Quitosano/síntesis química , Quitosano/farmacología , Óxido de Etileno/química , Nanopartículas/química , Triazoles/química , Aldehídos/química , Ampicilina/química , Exoesqueleto , Animales , Antiinfecciosos , Catálisis , Química Clic , Ésteres , Gentamicinas/química , Tecnología Química Verde , Iones , Espectroscopía de Resonancia Magnética , Solubilidad , Solventes , Viscosidad
13.
Food Chem ; 343: 128676, 2021 May 01.
Artículo en Inglés | MEDLINE | ID: mdl-33250292

RESUMEN

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.


Asunto(s)
Antiinfecciosos/química , Quitosano/química , Embalaje de Alimentos/métodos , Nanopartículas/química , Antiinfecciosos/farmacología , Antioxidantes/química , Queso/análisis , Escherichia coli/efectos de los fármacos , Hongos/efectos de los fármacos , Taninos Hidrolizables/química , Metilcelulosa/química , Nanopartículas/toxicidad , Polietilenglicoles/química , Staphylococcus aureus/efectos de los fármacos , Temperatura , Resistencia a la Tracción
14.
SAGE Open Med Case Rep ; 8: 2050313X20981464, 2020.
Artículo en Inglés | MEDLINE | ID: mdl-33489233

RESUMEN

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.
Artículo en Inglés | MEDLINE | ID: mdl-31490126

RESUMEN

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.


Asunto(s)
Gnathostoma/anatomía & histología , Gnathostoma/genética , Gnathostomiasis/veterinaria , Enfermedades de los Porcinos/parasitología , Animales , ADN Espaciador Ribosómico/análisis , Complejo IV de Transporte de Electrones/análisis , Femenino , Gnathostomiasis/parasitología , Proteínas del Helminto/análisis , Masculino , Filogenia , Sus scrofa , Porcinos , Vietnam
16.
Emerg Infect Dis ; 25(7): 1433-1435, 2019 07.
Artículo en Inglés | MEDLINE | ID: mdl-31075078

RESUMEN

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.


Asunto(s)
Fiebre Porcina Africana/epidemiología , Fiebre Porcina Africana/historia , Fiebre Porcina Africana/virología , Animales , Asfarviridae/clasificación , Asfarviridae/genética , ADN Viral , Brotes de Enfermedades , Genes Virales , Genotipo , Secuenciación de Nucleótidos de Alto Rendimiento , Historia del Siglo XXI , Filogenia , Análisis de Secuencia de ADN , Porcinos
17.
Nat Prod Commun ; 11(12): 1789-1792, 2016 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-30508334

RESUMEN

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.


Asunto(s)
Antineoplásicos , Artemisininas , Triazoles , Zidovudina , Antineoplásicos/química , Antineoplásicos/farmacología , Artemisininas/química , Artemisininas/farmacología , Supervivencia Celular/efectos de los fármacos , Química Clic , Células Hep G2 , Humanos , Células KB , Triazoles/química , Triazoles/farmacología , Zidovudina/química , Zidovudina/farmacología
18.
Bioorg Med Chem Lett ; 24(10): 2244-6, 2014 May 15.
Artículo en Inglés | MEDLINE | ID: mdl-24745968

RESUMEN

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.


Asunto(s)
Oligopéptidos/síntesis química , Ensayos de Selección de Medicamentos Antitumorales , Células Hep G2 , Humanos , Células KB , Células MCF-7 , Oligopéptidos/química , Oligopéptidos/farmacología , Relación Estructura-Actividad
19.
Chemistry ; 19(19): 5966-71, 2013 May 03.
Artículo en Inglés | MEDLINE | ID: mdl-23512331

RESUMEN

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.


Asunto(s)
Azetidinas/síntesis química , Aziridinas/síntesis química , Dioxanos/síntesis química , Compuestos Heterocíclicos/química , Hidrocarburos Fluorados/química , Hidrocarburos Fluorados/síntesis química , Morfolinas/síntesis química , Oxígeno/química , Quinolizinas/síntesis química , Compuestos de Azufre/síntesis química , Azufre/química , Trifluoroetanol/análogos & derivados , Trifluoroetanol/química , Azetidinas/química , Aziridinas/química , Dioxanos/química , Morfolinas/química , Quinolizinas/química , Estereoisomerismo , Compuestos de Azufre/química
20.
Bioorg Med Chem Lett ; 15(10): 2629-31, 2005 May 16.
Artículo en Inglés | MEDLINE | ID: mdl-15863331

RESUMEN

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.


Asunto(s)
Antimaláricos/síntesis química , Artemisininas/síntesis química , Animales , Antimaláricos/farmacología , Artemisininas/farmacología , Plasmodium falciparum/efectos de los fármacos
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