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Furanoterpene diversity and variability in the marine sponge Spongia officinalis, from untargeted LC-MS/MS metabolomic profiling to furanolactam derivatives

The Mediterranean marine sponge Spongia officinalis has been reported as a rich source of secondary metabolites and also as a bioindicator of water quality given its capacity to concentrate trace metals. In this study, we evaluated the chemical diversity within 30 S. officinalis samples collected over three years at two sites differentially impacted by anthropogenic pollutants located near Marseille (South of France). Untargeted liquid chromatography?mass spectrometry (LC-MS) metabolomic profiling (C18 LC, ESI-Q-TOF MS) combined with XCMS Online data processing and multivariate statistical analysis revealed 297 peaks assigned to at least 86 compounds. The spatio-temporal metabolite variability was mainly attributed to variations in relative content of furanoterpene derivatives. This family was further characterized through LC-MS/MS analyses in positive and negative ion modes combined with molecular networking, together with a comprehensive NMR study of isolated representatives such as demethylfurospongin-4 and furospongin-1. The MS/MS and NMR spectroscopic data led to the identification of a new furanosesterterpene, furofficin (2), as well as two derivatives with a glycinyl lactam moiety, spongialactam A (12a) and B (12b). This study illustrates the potential of untargeted LC-MS metabolomics and molecular networking to discover new natural compounds even in an extensively studied organism such as S. officinalis. It also highlights the effect of anthropogenic pollution on the chemical profiles within the sponge.

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A Novel One-Step Synthesis of 4H-Furo<3,4-b>pyrans and a Transformation into a Difuro<3,4-b:3',4'-e>pyridine

A simple one-step synthesis of 2-amino-4-aryl-5-oxo-4H-furo<3,4-b>pyran-3-carbonitriles 7 is described.It involves reaction of 2,4(3H,5H)-furandione (beta-tetronic acid) (5) with arylmethylenemalononitriles 4 in basic medium.Some substituent effects are noted and the assignments of 13C-NMR spectra are discussed.Ring transformation of the furo<3,4-b>pyran 7a leads to the difuro<3,4-b:3',4'-e>pyridine 9.Key Words: Furo<3,4-b>pyrans / Difuro<3,4-b:3',4'-e>pyridine / beta-Tetronic acid / Malononitriles, arylmethylene-

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Exploring the one-pot C-acylation of cyclic 1,3-diones with unactivated carboxylic acid

The use of DCC, triethylamine, and 4-dimethylaminopyridine in dichloromethane provides a general and standard one-pot procedure for the C-acylation of cyclic 1,3-diones with a wide range of carboxylic acids, giving rise to beta-triketones in good to excellent yields.

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In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 4971-56-6, name is Furan-2,4(3H,5H)-dione, introducing its new discovery. category: Tetrahydrofurans

An efficient three-component tandem reaction leading to pentacyclic isoindole-fused benzo[b,e][1,4]diazepines in water

An efficient methodology for the synthesis of highly functionalized pentacyclic isoindole-fused benzo[b,e][1,4]- diazepine derivatives from readily available common reactants in water has been developed. The tandem reaction resulted in efficient assembly of two new rings and four. bonds including three CN bonds in a one-pot operation.

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Synthesis of Pyrano[2, 3-d]Pyrimidine-2,4(3H)-Dione Derivatives Based-on Curcumin Using NiCo2O4@OCMC@Zn(BDC) Nanocomposite as a Novel and Efficient Catalyst

Curcumin, a category of phenolic compound derivatives from the base of Curcuma longa (Zingiberaceae), represent a variety of beneficial effects on health and on events that succor in hampering certain diseases. The present research explains an efficient procedure for the synthesis of pyrano[2,3-d] pyrimidine-2,4(3H)-diones in high yields and short response times via a three-ingredient reaction of curcumin, aromatic aldehydes and 1,3-dimethylbarbituric acid in the presence of NiCo2O4@OCMC@Zn(BDC) nanocomposite. The catalyst was determined by scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), Fourier transform infrared, (FT-IR) X-ray powder diffraction (XRD) and Brunauer?Emmett?Teller (BET). Moreover, the NiCo2O4@OCMC@Zn(BDC) catalyst can be recovered and reused several times without significant loss of its activity.

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alpha-((Tetronoyl)oxy)- and alpha-((tetramoyl)oxy)methyl ketone inhibitors of the interleukin-1beta converting enzyme (ICE)

Aryl-substituted tetronic acids, tetramic acids, and cyclic P-dicarbonyl moieties were evaluated as leaving groups in the peptidyl-COCH2-X type inhibitor iii. Tripeptidyl aspartyl alpha-((tetronoyl)oxy)- and alpha-((tetramoyl)oxy)methyl ketone derivatives demonstrate potent time-dependent inhibition (k(obs)/[I] 100,000-250,000 M-1 s-1) of the cysteine protease ICE.

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Catalytic processes in vitamins synthesis and production

Water- and fat-soluble vitamins are essential for human and animal nutrition. Several of them are produced in amounts of well above 1000 t annually worldwide. In this highly competitive field, catalytic methods represent ideal tools to lower production costs, and consequently gain an economical advantage, by the application of environmentally benign processes. Examples of industrially important transformations given in this review are grouped by reaction types, e.g. hydrogenation, oxidation and various alkylation, rearrangement, cycloaddition, and esterification reactions.

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Predictive QSAR modeling for the antioxidant activity of natural compounds derivatives based on Monte Carlo method

Abstract: In this research, QSAR modeling was carried out through SMILES of compounds and on the basis of the Monte Carlo method to predict the antioxidant activity of 79 derivatives of pulvinic acid, 23 of coumarine, as well as nine structurally non-related compounds against three radiation sources of Fenton, gamma, and UV. QSAR model was designed through CORAL software, as well as a newer optimizing method well known as the index of ideality correlation. The full set of antioxidant compounds were randomly distributed into four sets, including training, invisible training, validation, and calibration; this division was repeated three times randomly. The optimal descriptors were picked up from a hybrid model by the combination of the hydrogen-suppressed graph and SMILES descriptors based on the objective function. These models? predictability was assessed on the sets of validation. The results of three randomized sets showed that simple, robust, reliable, and predictive models were achieved for training, invisible training, validation, and calibration sets of all three models. The central decrease/increase descriptors were identified. This simple QSAR can be useful to predict antioxidant activity of numerous antioxidants. Graphic abstract: [Figure not available: see fulltext.].

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Synthesis of magnetic hollow mesoporous N-doped silica rods as a basic catalyst for the preparation of some spirooxindole-1,4-dihydropyridine derivatives

In this study, magnetic hollow mesoporous N-doped silica rods were successfully prepared via the in-situ calcination of different amounts of diethanolamine in the presence of silica precursor. Doping of the nitrogen atoms in to silica rod structures was performed through a new method and the structure of obtained composite confirmed by X-ray photo electron spectroscopy (XPS), X-ray diffraction (XRD) analysis, elemental analysis, TEM, FESEM and elemental mapping methods. Comparison of the synthesized N-doped catalyst with the same sample without nitrogen atoms (mesoporous silica) showed the high basic characteristic. Furthermore, the efficiency of the prepared basic catalyst was investigated for the synthesis of some spirooxindole-1,4-dihydropyridine derivatives under green conditions. High efficient heterogeneous catalyst, short reaction times (compare with other reported methods) and green conditions are some advantageous of presented method.

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Facile and clean synthesis of furopyridine derivatives via three-component reaction in aqueous media without catalyst

A series of furo[2?,1?:5,6]pyrido[2,3-d]pyrimidine derivatives were synthesized via the three-component reaction of an aldehyde, tetronic acid, and 6-amino-1,3-dimethyl-pyrimidine-2,4-dione in aqueous media without the use of catalyst. This protocol has the advantages of better yields, less cost, reduced environmental impact, and convenient procedure.

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