RESUMEN
A hybrid pharmacophore strategy for unifying 1,2,3-triazole with 1,2,4-triazole cores to prepare mixed triazoles was accomplished by a ball-milling approach. The developed chemistry works under the catalysis of cupric oxide nanoparticles with salient features like one-jar operation, lower number of synthetic steps, catalyst recyclability, time-dependent product control, and good overall yields. π-Orbital properties based on theoretical calculations supported the suitability of these molecules for pharmacological screening. Therefore, the biological potency of the synthesized molecules was evaluated for antioxidant, anti-inflammatory, and anti-diabetic activities. By virtue of their proton-donating tendency, all compounds showed promising radical-scavenging activity with the inhibition level reaching up to 90 %. These molecular hybrids also exhibited anti-inflammatory and anti-diabetic potencies similar to those of standard compounds, owing to their electron-rich nature. Finally, α-amylase inhibitory potential was demonstrated in silico; significant regions necessary for enzyme inhibition were identified by hydrogen bonding interactions.
Asunto(s)
Azoles , Triazoles , Azoles/farmacología , Simulación del Acoplamiento Molecular , Triazoles/química , Antioxidantes/farmacología , Antiinflamatorios/farmacología , Relación Estructura-Actividad , Estructura MolecularRESUMEN
Rhodamine-based chromic materials have attracted significant interest owing to their cation recognition ability with high sensitivity. However, rhodamine chromophores with controllable sensing selectivity towards transition metal species are only at the advent. Herein, three triazole-conjugated rhodamine dyads with different peripheral substituents were synthesized. The key triazole precursors required for the desired chemistry were prepared by adopting our recently developed CTAB catalyzed mechano-click chemistry. Molecular properties derived from photophysics, electrochemistry and surface morphology of the synthesized dyads were analyzed. Furthermore, frontier molecular orbitals, electronic structure and secondary quantum chemical parameters of dyads were also compared. Screening of dyads for their sensing ability towards an array of alkali, alkaline and transition metal ions exhibited a noticeable naked-eye detection of Cu2+ ions and was confirmed by spectrophotometric titration. The specific binding mode of dyads as probable with Cu2+ over other metal ions attributes to the chemoselectivity.
RESUMEN
Chemical structures possessing both 1,2,3-triazole and bis(indolyl)methane fragments gained considerable interest in drug synthesis owing to their established biological efficacies. However, 1,2,3-triazoles linked at the bridging position of bis(indolyl)methane is a logical and unexplored design approach. In this regard, nine new triazolyl-bis(indolyl)methane conjugates under AuCl catalyzed ball-milling conditions were accomplished. Comparative evaluation on absorptive and emissive properties of the synthesized dyads were also analyzed. To unravel the influence of different peripheral substituents on the electronic structure and π-orbital properties, theoretical investigations were performed. Screening of molecules for free radical scavenging, anti-inflammatory and antidiabetic showed comparable potency against reference drugs. In particular, compounds 7 h, 7 d and 7 a displayed good efficiency of α-amylase inhibition. The DNA gyrase inhibitory potential of all compounds were assessed in silico which revealed high binding affinity (ΔG=-8.99 Kcal/mol) for 7 i followed by 7 h (ΔG=-7.80 Kcal/mol) with the targeted protein.
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Metano , Farmacóforo , Metano/química , Indoles/química , Catálisis , Triazoles/farmacologíaRESUMEN
4-Nitro-1,2,3-triazoles are crucial precursors for high energy materials, and their practical synthesis is a long-standing problem. Herein, we communicate a mechanochemical route for the selective synthesis of 4-nitro-1,2,3-triazoles via organocatalyzed oxidative [3 + 2] cycloaddition between ß-nitrostyrenes and organic azides. Our conditions avoid divergent pathways and permit the retention of the valuable NO2 group on the product. Nontoxic catalyst, catalyst recyclability, no rigorous solvent-extraction, no toxic byproducts, atmospheric oxygen, and gram-scale synthesis are some of the salient features.
RESUMEN
A practical synthesis of isoxazole/isoxazoline derivatives via Machetti-De Sarlo reaction under sustainable conditions has been accomplished. This protocol involves the use of readily available 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) to catalyze the cyclocondensation of primary nitroalkanes with alkynes/alkenes to afford a library of isoxazole/isoxazoline products. From an eco-benign perspective, notable advantages of this method are as follows: (i) water as the solvent, (ii) air as the oxidant, (iii) transition metal-free, (iv) no base required, (v) no toxic byproduct, (vi) no need of solvent extraction, (vii) diverse substrate scope, (viii) high chemical yields, (ix) excellent chemo- and regioselectivity, (x) short reaction time, (xi) gram-scale synthesis, (xii) extension to heterogeneous version, and (xiii) catalyst recyclability. For these reasons, the developed method is appropriate for safe laboratory use and can be expected to inspire the progress of TEMPO-based organocatalysis for the preparation of isoxazole/isoxazoline moieties in an environmentally benign fashion.
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Enterocytozoon hepatopenaei (EHP) is a microsporidian parasite that causes hepatopancreatic microsporidiosis (HPM) in penaeid shrimp. HPM was observed in several countries, including Thailand and India; it has become a prominent pathogen in shrimp culture. Based on observations on EHP infection in the wild, the route of transmission has been hypothesized. Identification of artificial EHP infection procedures can facilitate our understanding of EHP transmission. Experimental transmission of EHP was attempted using the immersion and oral infections of infection. In the immersion mode, post-larvae (PL) were exposed to an EHP tissue homogenate (0.2%) by immersion for 48 hr. Experimental samples were collected at various time points, and infection was confirmed using polymerase chain reaction, haematoxylin and eosin staining, transmission electron microscopy and modified trichrome staining. All test results revealed successful EHP transmission. Similar results were obtained through oral infection (oral infection). Innate immune gene expression patterns during infection were analysed; prophenoloxidase, crustin and superoxide dismutase were upregulated at 6, 6 and 48 hr post-challenge, respectively. Experimental infection procedures facilitate the development of diagnostic and prevention strategies. This is the first study demonstrating the experimental transmission of EHP in shrimp PL.
Asunto(s)
Enterocytozoon/aislamiento & purificación , Microsporidiosis/transmisión , Penaeidae/microbiología , Animales , Péptidos Catiónicos Antimicrobianos/genética , Catecol Oxidasa/genética , Transmisión de Enfermedad Infecciosa/veterinaria , Enterocytozoon/genética , Precursores Enzimáticos/genética , Perfilación de la Expresión Génica , Inmunidad Innata/genética , Penaeidae/inmunología , ARN Mensajero , Superóxido Dismutasa/genéticaRESUMEN
OBJECTIVE@#To evaluate the anti-inflammatory and analgesic activities of the ethanol and aqueous extracts of prop roots of Pandanus fascicularis (P. fascicularis) Lam (pandanaceae). And provide experimental evidence for its traditional use such as rheumatoid arthritis and spasmodic.@*METHODS@#The anti-inflammatory activity was observed by carrageenan-induced edema of the hind paw of rats. Analgesic activities of prop roots of P. fascicularis were determined using acetic acid induced writhing model and tail clip method in mice and rat, respectively. The ethanol fraction was then subjected to chromatographic analysis and a compound has been isolated and characterized by IR, (1)H-NMR and mass spectroscopy.@*RESULTS@#Edema suppressant effect of ethanol extract was found to be 37.03% inhibition whereas aqueous extract was found to be 63.22% inhibition after 3 h which was nearly equivalent to that of 10 mg/kg of indomethacin (67.81%). Percentage inhibition of writhing compared to control were 63.15%, 54.38%, 14.90% for aspirin, aqueous extract and ethanolic extract, respectively. Both ethanol and aqueous extracts show significant activity against appropriate controls after 60 min of treatment on tail clip method. The structure of the isolated compound is may be characterized as Hepta deca-5-ene-1-ol by analysis it's IR, (1)H-NMR and mass spectroscopy data.@*CONCLUSIONS@#The extracts of prop roots of P. fascicularis produce significant analgesic and anti-inflammatory activities, supporting the traditional application of this herb in treating various diseases associated with inflammation and pain.