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Ciprofloxacin-induced acute psychosis in a patient with multidrug-resistant tuberculosis

Tuberculosis (TB) increasingly appears in a multidrug-resistant form (MDR-TB) in Europe, too. Treatment remains difficult due to various side effects of the multi-drug-regimens. Ciprofloxacin is widely used as one of the few TB-second-line drugs. We report on the course of a ciprofloxacin-induced acute psychosis in a patient with MDR(isoniazid, streptomycin)-TB which resolved after cessation of ciprofloxacin treatment and introduction of a novel oxazolidone. Careful treatment considerations particularly in patients with additional predisposing factors to neuropsychiatric symptoms are recommended in the potentially dangerous MDR-TB, thus creating an enormous therapeutic challenge.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H864NO – PubChem

 

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Approaches to Obtaining Fluorinated alpha-Amino Acids

Fluorine does not belong to the pool of chemical elements that nature uses to build organic matter. However, chemists have exploited the unique properties of fluorine and produced countless fluoro-organic compounds without which our everyday lives would be unimaginable. The incorporation of fluorine into amino acids established a completely new class of amino acids and their properties, and those of the biopolymers constructed from them are extremely interesting. Increasing interest in this class of amino acids caused the demand for robust and stereoselective synthetic protocols that enable straightforward access to these building blocks. Herein, we present a comprehensive account of the literature in this field going back to 1995. We place special emphasis on a particular fluorination strategy. The four main sections describe fluorinated versions of alkyl, cyclic, aromatic amino acids, and also nickel-complexes to access them. We progress by one carbon unit increments. Special cases of amino acids for which there is no natural counterpart are described at the end of each section. Synthetic access to each of the amino acids is summarized in form of a table at the end of this article with the aim to make the information easily accessible to the reader.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H838NO – PubChem

 

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Copper-catalyzed cross-coupling of amides and potassium alkenyltrifluoroborate salts: A general approach to the synthesis of enamides

Potassium alkenyltrifluoroborate salts undergo coupling with amides to give enamides using a catalytic amount of Cu(OAc)2 under mild oxidative conditions. The air and water stable alkenyltrifluoroborate salts offer a practical alternative to the use of alkenyl halides and alkenylboronic acids as cross-coupling partners. A range of amides participate in the cross-coupling, including heterocyclic amides, imides, carbamates, benzamides, and acetamides. Optimization studies established two sets of conditions, best suited to either high PKa or low PKa amide substrates. Lower PK amide substrates worked best using a dichloromethane solvent system in the presence of 4 A molecular sieves, 10 mol % Cu(OAc)2, and 20 mol % N-methylimidazole. Higher PKa amide substrates worked best using a ligandless protocol using a 1:1 dichloromethane/DMSO solvent system in the presence of 4 A molecular sieves and 10 mol % Cu(OAc)2. The cross-coupling reactions occur stereospecifically with retention of alkene configuration from the alkenyltrifluoroborate salt. The mild reaction conditions employed are tolerant of various functionalities, including nitro, acetals, alkyl and aryl halides, and alpha,beta-unsaturated carbonyls. Finally, the importance of copper sources and the presence of minor impurities were investigated.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H354NO – PubChem

 

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Acidic-functionalized ionic liquid as an efficient, green and reusable catalyst for hetero-Michael addition of nitrogen, sulfur and oxygen nucleophiles to alpha,beta-unsaturated ketones

A series of acidic-functionalized ionic liquids were synthesized and applied to the hetero-Michael addition of nitrogen, sulfur and oxygen nucleophiles to alpha,beta-unsaturated ketones under solvent-free conditions. Notably, 1-methylimidazolium p-toluenesulfonic ([Hmim]OTs) was found to be the most efficient catalyst and could realize “homogeneous catalysis, two-phase separation”. Additionally, the catalytic system has wide substrate scope and good to excellent yields (up to 99%) could be obtained at room temperature.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H585NO – PubChem

 

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Thermal stability and flame retardancy of polyurethanes

The thermal stability and flame retardancy of polyurethanes is reviewed. Polyurethanes (PUs) are an important class of polymers that have wide application in a number of different industrial sectors. More than 70% of the literature that deals with PUs evaluates their thermal stability or flame retardancy and attempts to provide a structure-property correlation. The importance of studying thermal degradation, understanding the processes occurring during thermal stress as well as the parameters affecting the thermal stability of PUs are essential in order to effectively design polyurethanes having tailor-made properties suitable for the particular environment where they are to be used. A detailed description of TGA, TGA-MS and TGA-FTIR methods for studying the decomposition mechanism and kinetics is also a part of this review. In general, thermal decomposition of PUs begins with the hard segment (HS) and a number of parameters govern a polyurethane’s thermal stability. Detailed description of the parameters such as HS, soft segment (SS) and chain extender (CE) structure and molecular weight, NCO:OH ratio, catalyst nature and crosslink density that affect the nature of PU degradation is given. Descriptions of approaches to improve the thermal stability in PUs such as formation of poly(urethane-isocyanurate), poly(urethane-oxazolidone) and poly(urethane-imide) in addition to other methods such as PUs with an s-triazine ring or increased aromatic ring concentration, azomethane linkages as well as use of hyperbranched polyols as crosslinking agents is given. A part of the review is also concentrated on the improvement of thermal stability via hybrid formation such as the incorporation of appropriate amounts of fillers, e.g., nano-silica; Fe2O3; TiO2; silica grafting; nanocomposite formation using organically modified layered silicates; incorporation of Si-O-Si crosslinked structures via sol-gel processes; and the incorporation of polyhedral oligomeric silsesquioxane (POSS) structures into the PU backbone or side chain. Incorporation of carbon nanotubes (CNT) into PUs and the use of functionalized fullerenes in PUs are also described as these are the newest tools to obtain good thermal stability and flame retardancy. Part of the review also concentrates on the process that occurs during burning of PUs, flame retardant mechanisms and different additives or reactive type flame retardants used in the PU industry. The use and working function of expandable graphite and melamine as additive type flame retardants are shown. Description of the use of different reactive type organophosphorus compounds, cyclotriphosphazenes, aziridinyl curing agents in aqueous polyurethane dispersions (PUDs), organoboron compounds and organosilicon compounds for improving flame retardancy is also given.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H416NO – PubChem

 

Brief introduction of Oxazolidin-2-one

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Hafinium (IV) promoted synthesis of 2,3-unsaturated N- and C-pseudoglycosides via Type I Ferrier Rearrangement

By using Hf(OTf)4as the catalyst, a series of 2,3-N- and C-unsaturated-glucosides have been synthesized from 3,4,6-tri-O-acetyl-D-glucal, 2,4,6-tri-O-benzyl-D-glucal and ((2R,3S)-3-acetoxy-2,3-dihydrofuran-2-yl)methyl acetate under mild reaction conditions in good yields with high anomeric selectivities.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H427NO – PubChem

 

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Enantioselective conjugate addition of hydrazines to alpha,beta- unsaturated imides. Synthesis of chiral pyrazolidinones

This manuscript describes a highly enantioselective conjugate hydrazine addition to alpha,beta-unsaturated imides. The achiral template used has a significant impact on product enantioselectivity. Reactions at lower temperatures provide a protocol to add substituted hydrazines with selectivity resulting in the formation of a single pyrazolidinone product (>98:2 selectivity). A variety of chiral pyrazolidinones with potential as chiral auxiliaries and ligands are accessible through the new conjugate addition methodology. Copyright

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H998NO – PubChem

 

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Structural basis of translation inhibition by cadazolid, a novel quinoxolidinone antibiotic

Oxazolidinones are synthetic antibiotics used for treatment of infections caused by Gram-positive bacteria. They target the bacterial protein synthesis machinery by binding to the peptidyl transferase centre (PTC) of the ribosome and interfering with the peptidyl transferase reaction. Cadazolid is the first member of quinoxolidinone antibiotics, which are characterized by combining the pharmacophores of oxazolidinones and fluoroquinolones, and it is evaluated for treatment of Clostridium difficile gastrointestinal infections that frequently occur in hospitalized patients. In vitro protein synthesis inhibition by cadazolid was shown in Escherichia coli and Staphylococcus aureus, including an isolate resistant against linezolid, the prototypical oxazolidinone antibiotic. To better understand the mechanism of inhibition, we determined a 3.0 A cryo-electron microscopy structure of cadazolid bound to the E. coli ribosome in complex with mRNA and initiator tRNA. Here we show that cadazolid binds with its oxazolidinone moiety in a binding pocket in close vicinity of the PTC as observed previously for linezolid, and that it extends its unique fluoroquinolone moiety towards the A-site of the PTC. In this position, the drug inhibits protein synthesis by interfering with the binding of tRNA to the A-site, suggesting that its chemical features also can enable the inhibition of linezolid-resistant strains.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H961NO – PubChem

 

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Bi(OTf)3-catalyzed three-component synthesis of amidomethylarenes and -heteroarenes

A highly efficient Bi(OTf)3-catalyzed multicomponent synthesis of amidomethylated arenes and heteroarenes from readily available starting materials has been developed. This reaction proceeds under mild conditions, has a broad substrate scope, and in addition water is generated as only side product. Georg Thieme Verlag Stuttgart, New York.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H966NO – PubChem

 

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Complexation of Carbonyl Compounds with an Organic Salt Dominated by Acid-Base Interactions in Dichloromethane

Small neutral carbonyl compounds (2-5) form very stable complexes (Ka’s ranging from 1E3 to 1E5 M-1) with ethyl 2,6-diaminonicotinium tetrakis(3,5-bis(trifluoromethyl)phenyl)borate (1) in dichloromethane.The dominant driving force for complexation between the host and guest.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H345NO – PubChem