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Bellino, G.; Tidei, C.; Sancineto, L.; Bagnoli, L.; Marini, F.; Santi, C. Non Conventional Zinc Mediated Synthesis of Chalcogenoesters, in Proceedings of the 18th International Electronic Conference on Synthetic Organic Chemistry, 1–30 November 2014, MDPI: Basel, Switzerland, doi:10.3390/ecsoc-18-a040
Chalcogenoesters are important intermediates in several organic transformations, they were used as precursors of acyl radicals and anions and have attracted attention for the synthesis of new molecular materials, especially superconducting materials and liquid crystals. Applications of selenoesters have been expanded to the synthesis of proteins by chemical ligation, to the synthesis of substrates which undergo facile and efficient radical decarboxylation, as well as to the synthesis of the natural alkaloyd (+)- geissoschizine, ciguatoxins, and (-)- pseudolaric Acid B.We report here new zinc mediated and non-conventional protocols for their eco-friendly preparation.
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Maleki, A.; Jafari, A.; Yousefi, S.; Eskandarpour, V. One-Pot Multicomponent Synthesis of Pyrano[2,3-d]Pyrimidine Derivatives Catalyzed by Supported Magnetic Nanoparticles, in Proceedings of the 18th International Electronic Conference on Synthetic Organic Chemistry, 1–30 November 2014, MDPI: Basel, Switzerland, doi:10.3390/ecsoc-18-a041
Heterocycles are an important class of organic compounds, because of their biological and pharmaceutical activities. It is proved that heterocycles could have more attractive and beneficial properties when they are derived by fusion with other heterocyclic rings. For example, pyrimidine is one of the useful heterocycles that exhibit useful biological activities and clinical applications; it could have additive effect in combining with other heterocycles like pyran. The significance of pyranopyrimidine is due to the occurrence of the structure in many natural products.Nowadays, multicomponent reactions (MCRs) and magnetically nanocatalysts are coming to the aim of organic synthesis to improve synthetic routes. MCRs allow the formation of several bonds in a single operation so they offer remarkable advantages such as operational simplicity, reduction in the number of workup and extraction and purification processes. Magnetically nanocatalysts are accessible from inexpensive materials and could be separated from the product without filtration or centrifugation. So, magnetic separation is a green process and it avoids use of extra chemicals during the separation process. Herein, we have developed a synthetic route for one-pot three-component synthesis of annulated fused pyrano[2,3-d]pyrimidines from condensation of aromatic aldehydes, active methylene compounds and barbituric or thiobarbituric acid catalyzed by supported magnetic nanoparticles at room temperature. This efficient catalyst for the preparation of biologically and pharmaceutically pyrano[2,3-d]pyrimidine derivatives includes some important aspects like the easy workup procedure, reusability of catalyst as well as high atom economy, excellent yields, and mild reaction conditions.
In this study, nonionic surfactants were extracted from ginseng. The extraction of these surfactants from the plant was done by soxhlet. After the extraction, we used FT-IR spectroscopy for characterization of extracted saponin. Rates of change of water surface tension in terms of these surfactants concentration were obtained at 25°C. It shows that saponin as a surfactant decreased the surface tension of water. After that, the critical micelle concentration of these surfactants was obtained by curve of change of water surface tension in terms of change of these surfactants concentration.
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Shutalev, A.; Fesenko, A.; Albov, D.; Chernyshev, V.; Zamilatskov, I. Novel 14-Membered Hexaaza Macrocycles, in Proceedings of the 18th International Electronic Conference on Synthetic Organic Chemistry, 1–30 November 2014, MDPI: Basel, Switzerland, doi:10.3390/ecsoc-18-a042
An efficient method for the stereoselective synthesis of novel 14-membered cyclic bis-semicarbazones based on acid-catalyzed cyclization of the hydrazones of 3-(3-oxobutyl)semicarbazides has been developed. The starting semicarbazides were prepared according to a four-step strategy involving amidoalkylation of the sodium enolate of acetylacetone with N-(α-tosylbenzyl)carbamates followed by base-promoted retro-Claisen reaction and treatment of the obtained N-(3-oxobutyl)carbamates with hydrazine.
The present study highlights the importance of Terminalia chebula Linn, a plant used in traditional system of medicine for various disorders. This study was aimed at the evaluation of the anti-inflammatory activity of marker compound (chebulinic acid) from the pericarp of fruits of Terminalia chebula. There have been a number of reports in the literature, where the hydrolytic products of chebulinc acid i.e. gallic acid, ellagic acid and galloyl derivatives have shown marked anti-inflammatory properties, however the antiinflammatory properties of chebulinic acid have not been determined. As denaturation of protein is one of the major reason, which is responsible for inflammation, the activity was determined in terms of its ability to inhibit denaturation of proteins. Chebulinic acid was incubated at different concentrations ranging from 0.0 - 100.0 µg/ml with egg albumin in controlled experimental conditions and subjected to determination of absorbance and viscosity to assess the anti-inflammatory property. Chebulinic acid efficiently reduced the denaturation of protein in terms of percentage inhibition (IC50 - 43.92 µg/ml). The percentage inhibition was comparable with that of standard (diclofenac sodium) having IC50 value 47.04 µg/ml. Our study is the first report which focuses on anti-inflammatory response of chebulinic acid against denaturation of proteins. Since, the results are comparable with diclofenac sodium. The plants as well as compound can be taken for further in-vivo studies.
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Jain, P.K.; Patra, A.; Jain, S.; Khan, S.; Satpathy, S. Antibacterial and Antioxidant Activities of 3-O-methyl Ellagic Acid 4'-rhamnoside from Stem Bark of Polyalthia longifolia Thw., in Proceedings of the 18th International Electronic Conference on Synthetic Organic Chemistry, 1–30 November 2014, MDPI: Basel, Switzerland, doi:10.3390/ecsoc-18-b031
The plant Polyalthia longifolia (Annonaceae) is an ornamental tree that finds its reference in Indian medicinal literature owing to its popular Hindi name Ashoka i.e, Saraca indica. However, P. longifolia is equated with the name Asoka and often used as an adulterant or substitute of the genuine Asoka bark. The present investigation was carried out with an object to separate and isolate active phytomolecule(s) from stem bark of P. longifolia and to screen their antibacterial and antioxidant potential. Column chromatography of the butanol fraction of the hydroalcoholic extract (methanol:water, 1:1) has led to the isolation of a phenolic compound. Structural elucidation was done by IR, 1H NMR, 13C NMR, DEPT, COSY, HSQC, HMBC and mass spectroscopy techniques, and purity was checked by HPTLC and HPLC. Butanol fraction and the isolated compound were screened for antibacterial activity (against facultative aerobic and fastidious aerobic bacterial strains) and antioxidant potential (DPPH method). The compound was revealed to be 3-O-methyl ellagic acid 4'-rhamnoside (1), and the purity of the compound was 99.2%. The isolated compound comprises promising antibacterial and antioxidant activities.
Recently, great efforts were made to use green and environmentally friendly methods for the synthesis of nano size materials. These efforts involve the use of plant or fruit extracts as surfactants. Plant parts such as leaf, root, latex, seed, and stem are being used for metal nanoparticles synthesis. The greener environmentally friendly processes in chemistry and chemical technology are becoming increasingly popular. The techniques for obtaining nanoparticles using naturally occurring reagents such as plant extract, could be considered attractive for nanotechnology. Magnetic nanoparticles have attracted a great attention due to their unique physical, chemical and structural properties when the particle sizes approach to nanoscale. It is these unique features that endow magnetic nanoparticles with wide applications, such as magnetic storage, catalysis, microwave absorption, magnetic resonance contrast, cancer hyperthermia, cell separation and drug delivery. In this work, we present a novel green and cost-efficient method for synthesis of superparamagnetic magnetite nanoparticles with an average diameter of 30-46 nm by coprecipitation method and using Acanthophyllum Bracteatum extract as surfactant. We used soxhlet extractor as extraction technique. The sample was characterized by vibrating sample magnetization (VSM), scanning electron microscopy (SEM), X-ray diffraction (XRD), fourier-transform infrared spectroscopy (FTIR).
The human immunodeficiency virus (HIV) is the causative agent of the acquired immunodeficiency syndrome (AIDS) that has been affected 34 million people worldwide. Though an unprecedented growth has been taken place in the development of anti-HIV drugs during the last two decades, there is still no cure for this deadly disease. Cross resistance to anti HIV drugs is also a major concern in the development of anti AIDS pharmaceuticals. Therefore, nowadays studies are being focused mainly on the development of newer drugs capable of inhibiting resistant mutants. HIV-1-RT is one of the major targets for the development of newer molecular entities (NMEs) for the treatment of HIV/AIDS. Inhibitors of HIV-1-RT are classified as nucleoside reverse transcriptase inhibitors (NRTIs) and non nucleoside reverse transcriptase inhibitors (NNRTIs). A compound incorporating the pyrazole structural unit, lersiverine was reported recently, as a NNRTI. The objective of this study was to elucidate the binding mode analysis of novel pyrazole analogs in the non nucleoside inhibitory binding pocket of reverse transcriptase (PDB ID IRT2). Molecular docking studies of 484 novel pyrazole analogs were performed by Glide program in the NNIBP of HIV-1 reverse transcriptase (PDB code 1RT2).The Novel pyrazole analogs bearing different substituted aryl groups were designed The following eight compounds with aryl substituents like R=2,5-2CH3 &R1= m-OCH3 , R=H &R1=m-OCH3,R=H &R1=m-CH3, R=o-Cl &R1=m-OCH3, R=o-Cl &R1=p-OCH3, R=m-CH3 &R1=m-CH3, R=m-Cl &R1=m-Cl, R=m-Cl &R1=2,4-2NO2, exhibited highest docking score in the NNIBP of IRT2 . Thus, it is evident that this kind of scaffold with hydrophobic and electron donating or electron withdrawing groups substituted in the phenyl rings can be exploited for the development of novel HIV-1-RT2 inhibitors which can facilitate better patient adherence and also inhibit the resistant strains of HIV.
The frequency of opportunistic fungal infection has increased drastically, mainly in patients who are immunocompromised due to organ transplant, leukaemia or HIV infection. Candida albicans is responsible for most infections caused by fungi; however, the incidence of non-albicans species that are resistant, less susceptible or potentially resistant to currently antifungal drugs, such as Candida parapsilosis, Candida krusei, Candida tropicalis, appears to be increasing. Filamentous fungi infections are less frequent than Candida species infection, but are associated with high mortality rates. Despite the addition of new classes of antifungals, the number of currently available drugs for the treatment of fungal infections remains limited.Perylene derivatives are compounds used in a variety of industrial applications for decades, especially in the dye-sensitized solar cells, organic light-emitting diodes, and organic thin film transistors. Moreover, these compounds have shown some anticancer, antiviral, antidepressant, and antibacterial activities.In this study, we have synthesized several perylene bisimide derivatives and evaluated the antifungal activity against human pathogenic yeasts (Candida spp.) and filamentous fungi (Aspergillus spp., Fusarium spp., and Trichophyton spp.).Three compounds (2-4) from the nine compounds tested presented relevant activity. Compound 2 was active against Candida albicans, C. parapsilosis and C. tropicalis with minimum inhibitory concentrations (MIC90) values of 25.0, 22.0 and 14.0 µg/mL, respectively. Similarly, compound 3 was active against these three yeasts with MIC90 values of 7.0, 5.0 and 6.0 µg/mL, respectively, while compound 4 showed a MIC90 value below 3,1 µg/mL, being this compound the most potent. These three compopunds also showed activity against filamentous fungi, F. oxysporum, T. rubrum and T. mentagrophytes at a concentration of 50 µg/mL. The resultant data indicates that perylene bisimides (2-4) display wide spectrum and relevant antifungal activity. Compound 4 represents a new scaffold for the development of antifungal agents and warrant further structure activity relationship studies.
Alzheimer´s disease (AD) is a progressive neurodegenerative disorder associated with memory impairment and cognitive deficit. It is characterized by low levels of the neurotransmitter acetylcholine (ACh) in the brain of AD patients. The inhibition of acetylcholinesterase (AChE), the enzyme that catalyzes ACh hydrolysis, is the main therapeutic strategy used to treat AD. In the healthy brain, another enzyme, namely butyrylcholinesterase (BChE), is involved in the metabolic degradation of ACh. BChE activity increases as AD progresses, which suggests that BChE may play an important role at the latter stages of AD. Therefore, selective BChE inhibitors attract interest nowadays. The chemistry of lupane-type triterpenoids has been actively explored due to their biological and pharmacological properties. Abundant in many plants, these metabolites are valuable natural raw materials to perform chemical modifications. In the present work, we aimed to evaluate of natural and semisynthetic lupanes as potential in vitro cholinesterase inhibitors. Lupeol (1) (lup-20(29)-en-3β-ol) and calenduladiol (2) (lup-20(29)-en-3β,16β-diol) have been isolated from Chuquiraga erinacea subsp. erinacea (Asteraceae), an endemic species growing wildly in our region. Semisynthetic lupanes 3-16 have been prepared from them. All of them failed to inhibit AChE, but we found that most of them exhibited BChE inhibition. The best BChE inhibitors were 16-oxolup-20(29)-en-3β-ol and 3,16,30-trioxolup-20(29)-ene with IC50 values of 28.9 and 21.5 µM respectively, an interesting result considering that the role of BChE is more relevant as the disease progresses.