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Enamide-benzyne-[2 + 2] cycloaddition: Stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions

Image Presented Benzyne-[2 + 2] cycloadditions with enamides are described. This effort led to the development of a highly stereoselective tandem [2 + 2] cycloaddition-pericyclic ring-opening-intramolecular-N-tethered-[4 + 2] cycloaddition for rapid assembly of nitrogen heterocycles.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H519NO – PubChem

 

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A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides

A copper-catalyzed new C-N bond formation involving a sp-hybridized carbon is described here leading to a facile entry for syntheses of chiral ynamides. This direct N-alkynylation of amides should have a significant impact on the future development of synthetic methodologies employing ynamides. Copyright

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Reference:
Oxazolidine – Wikipedia,
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Design, synthesis, and structure-activity and structure-pharmacokinetic relationship studies of novel [6,6,5] tricyclic fused oxazolidinones leading to the discovery of a potent, selective, and orally bioavailable FXa inhibitor

The blood coagulation enzyme factor Xa (FXa) is a particularly promising target for anticoagulant therapy, and identification of oral small-molecule inhibitors of FXa remains a research focus. On the basis of the X-ray crystal structure of FXa and its inhibitor rivaroxaban, we designed and synthesized a series of conformationally restricted mimics containing a novel [6,6,5] tricyclic fused oxazolidinone scaffold. Intensive structure-activity relationship (SAR) and structure-pharmacokinetic relationship (SPR) studies on this new series led to the discovery of compound 11a: a highly potent, selective, direct, and orally bioavailable FXa inhibitor with excellent in vivo antithrombotic efficacy and preferable pharmacokinetic profiles. Druggability evaluation of compound 11a was undertaken and elicited positive outcomes. All results indicate that compound 11a is a promising drug candidate for the prevention and treatment of thromboembolic diseases in venous and arterial systems.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1158NO – PubChem

 

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Emerging drugs for nosocomial pneumonia

Introduction: Hospital-acquired pneumonia (HAP) is one of the leading nosocomial infections worldwide and is associated with an elevated morbidity and mortality and increased hospital costs. Nevertheless, prompt and adequate antimicrobial treatment is mandatory following VAP development, especially in the face of multidrug resistant pathogens. Areas covered: We searched Pubmed and ClinicalTrials.gov site reports in English language of phase III clinical trials, between 2000?2016 referring to the antibiotic treatment of nosocomial pneumonia. We provide a summary of latest approved drugs for HAP and emerging drugs with potential indication nosocomial pneumonia. Expert opinion: There are several promising compounds on their way, as tedizolid-a new oxazolidone, iclaprim-a novel drug, related to trimethoprim, plazomicin-a new aminoglycoside and two combinations of ceftazidime/avibactam and ceftolozane/tazobactam against MDR bacteria, especially against MRSA and Gram-negative ESBL bacteria.

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Oxazolidine – Wikipedia,
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Glucosinolates: Molecular structure, breakdown, genetic, bioavailability, properties and healthy and adverse effects

Glucosinolates are a large group of plant secondary metabolites with nutritional effects and biologically active compounds. Glucosinolates are mainly found in cruciferous plants such as Brassicaceae family, including common edible plants such as broccoli (Brassica oleracea var. italica), cabbage (B. oleracea var. capitata f. alba), cauliflower (B. oleracea var. botrytis), rapeseed (Brassica napus), mustard (Brassica nigra), and horseradish (Armoracia rusticana). If cruciferous plants are consumed without processing, myrosinase enzyme will hydrolyze the glucosinolates to various metabolites, such as isothiocyanates, nitriles, oxazolidine-2-thiones, and indole-3-carbinols. On the other hand, when cruciferous are cooked before consumption, myrosinase is inactivated and glucosinolates could be partially absorbed in their intact form through the gastrointestinal mucosa. This review paper summarizes the glucosinolate molecular breakdown, their genetic aspects from biosynthesis to precursors, their bioavailability (assimilation, absorption, and elimination of these molecules), their sensory properties, identified healthy and adverse effects, as well as the impact of processing on their bioavailability.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H912NO – PubChem

 

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Direct oxidative allylic and vinylic amination of alkenes through selenium catalysis

Bringing “N” into the game: The direct chemoselective nitrogenation of unactivated alkenes can be achieved through oxidative selenium catalysis (see scheme). This method provides a broad variety of allylic imides in yields of up to 89 % using N-fluorobenzenesulfonimide (NFSI) as the terminal oxidant and nitrogen source. Furthermore, an unprecedented selenium-catalyzed vinylic C(sp2)-H nitrogenation was discovered. Copyright

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AN OXAZOLIDONE RING CONTAINING VINYL ESTER RESIN AND PRODUCTS THEREFROM

A process comprising contacting a) an epoxy resin; b) an adduct comprising at least one oxazolidone ring prepared from a multifunctional epoxy resin and an isocyanate compound; and c) an unsaturated acid to form a vinyl ester, is disclosed.

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Glucosinolate turnover in Brassicales species to an oxazolidin-2-one, formed via the 2-thione and without formation of thioamide

Glucosinolates are found in plants of the order Brassicales and hydrolyzed to different breakdown products, particularly after tissue damage. In Barbarea vulgaris R.Br. (Brassicaceae), the dominant glucosinolate in the investigated ?G-type? is glucobarbarin, (S)-2-hydroxy-2-phenylethylglucosinolate. Formation of the nitrile from glucobarbarin was observed in vitro, while a previously suggested thioamide (synonym thionamide) was not confirmed. Resedine (5-phenyl-1,3-oxazolidin-2-one) was detected after glucobarbarin hydrolysis in crushed B. vulgaris leaves and siliques, but not in intact parts. The abundance increased for several hours after completion of hydrolysis. The corresponding 1,3-oxazolidine-2-thione (OAT), with the common name barbarin, was also formed, and appeared to be the precursor of resedine. Addition of each of two non-endogenous OATs, (S)-5-ethyl-5-methylOAT and (R)-5-vinylOAT (R-goitrin), to a leaf homogenate resulted in formation of the corresponding 1,3-oxazolidin-2-ones (OAOs), confirming the metabolic connection of OAT to OAO. Formation of OAOs was inhibited by prior brief heating of the homogenate, suggesting enzyme involvement. We suggest the conversion of OATs to OAOs to be catalyzed by an enzyme (?oxazolidinethionase?) responsible for turnover of OAT formed in intact plants. Resedine had been reported as an alkaloid from another species – Reseda luteola L. (Resedaceae) – naturally containing the glucosinolate glucobarbarin. However, resedine was not detected in intact R. luteola plants, but formed after tissue damage. The formation of resedine in two families suggests a broad distribution of putative OATases in the Brassicales; potentially involved in glucosinolate turnover that needs myrosinase activity as the committed step. In agreement with the proposed function of OATase, several candidate genes for myrosinases in glucosinolate turnover in intact plants were discovered in the B. vulgaris genome. We also suggest that biotechnological conversion of OATs to OAOs might improve the nutritional value of Brassicales protein. HPLC-MS/MS methods for detection of these glucobarbarin products are described.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H273NO – PubChem

 

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Methods of inhibiting and treating biofilms using glycopeptide antibiotics

The present invention is directed to methods of inhibition, delay of formation, treatment, prophylaxis and/or prevention of infections caused by bacteria that exhibit tolerance to antimicrobial agents, including slow growing, stationary-phase and biofilm forming bacteria, through the use of glycopeptide antibiotics, such as oritavancin.

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Copper-catalyzed carboarylation of alkynes via vinyl cations

Copper-catalyzed arylation of electron rich alkynes reveals stabilized trisubstituted vinyl cation equivalents that react with pendant arene nucleophiles to form all carbon tetrasubstituted alkenes. The new process streamlines the synthesis of important medicinally relevant molecules.

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Oxazolidine – Wikipedia,
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