Archives for Chemistry Experiments of Isoxazolidine hydrochloride

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Synthesis and antimicrobial activity of 4H-4-oxoquinolizine derivatives: Consequences of structural modification at the C-8 position

The antibacterial 4H-4-oxoquinolizines were introduced recently to overcome bacterial resistance to fluoroquinolones. They exhibit potent antibacterial activity against Gram-positive, Gram-negative, and anaerobic organisms and are highly active against some quinolone-resistant bacteria including quinolone-resistant MRSA. Preliminary studies indicated that oxoquinolizines possess distinct activity and toxicity profiles as compared with their parent quinolones. In order to develop a potent antibacterial agent with the desired spectrum of activity, good tolerability, and balanced pharmacokinetic profile, we synthesized and evaluated a series of oxoquinolizines with various substituents at the C-8 position. Most compounds tested in this study demonstrated better activity against Gram-positive bacteria than ciprofloxacin and exhibited good susceptibility against ciprofloxacin- and methicillin-resistant S. aureus. While maintaining potent in vitro activity, several compounds showed improved in vivo efficacy over ABT-719 as indicated by the mouse protection test. As an example, the oral ED50 values for the cis-3-amino-4-methylpiperidine analogue 3ss against S. aureus NCTC 10649M, S. pneumoniae ATCC 6303, and E. coli JUHL were 0.8, 2.0, and 1.4 mg/kg, compared to 3.0, 10.0, and 8.3 mg/kg for ABT-719. The current study revealed that the steric and electronic environment conformation, and absolute stereochemistry of the C-8 group are very important to the antibacterial profiles. Structural modifications of the C-8 group provide a useful means to improve the antibacterial activities, physicochemical properties, and pharmacokinetic profiles. Manipulation of the C-8 group also allows us to generate analogues with the desired spectrum of activity, such as analogues that are selective against respiratory pathogens.

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THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE

Provided are methods of treating a cancer characterized by the presence of a mutant allele of IDH1/2 comprising administering to a subject in need thereof a compound described here.

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High service temperature, self-mendable thermosets networked by isocyanurate rings

A new mending chemistry exhibiting stability at extreme temperatures and holding mechanical properties as well as mechanical stability comparable to widely used engineering plastics is reported here. This mendable thermoset polymer is synthesized using commodity reactants through the formation of an isocyanurate-oxazolidone network which exhibit a high service temperature as shown by their Tg of 270?C and Td of 365?C. We demonstrate that this network polymer is repeatedly self-mendable in the presence of a macroscopic crack, yielding considerable recovery of the polymer’s strength after thermal annealing. This self-mending behavior is derived from a high density of mechano-responsive isocyanurate rings which are introduced as cross-links in the network. After mechanically initiated cycloreversion, the recovery of isocyanurate rings in a solid state is thermally initiated. This research is the first demonstration of an isocyanurate ring as a repairing moiety. We developed a new class of intrinsic self-mendable polymers withstanding high temperatures, which will greatly impact the application of thermoset polymers in the field of structural laminates and electronics packaging.

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Hepatitis C Virus Inhibitors

The present disclosure is generally directed to antiviral compounds, and more specifically directed to combinations of compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such combinations, and methods for inhibiting the function of the NS5A protein.

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Extended knowledge of (R)-4-Benzyl-2-oxazolidinone

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Total synthesis of (-)-mucocin

An enantioselective total synthesis of (-)-mucocin has been completed. A combination of asymmetric glycolate aldol additions and ring closing metathesis reactions were exploited to construct the C18-C34 and C7-C17 fragments. A selective cross-metathesis reaction was employed as the key step to couple two complex fragments.

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Reinforced isocyanurate/oxazolidone polymers for structural composites application

A new liquid injection system suitable for molding by RIM, RTM and cast techniques is discussed. This material which is based upon an oxazolidone/urethane modified polyisocyanurate is characterized by its ultra low viscosity, low reaction exotherms and a controllable cure time, thus making it ideal for making large and complex structural parts, particularly those requiring high levels of reinforcement. Copyright 1988 Society of Automotive Engineers, Inc.

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1H NMR Spectroscopic Studies on the Reactions of Haloalkylamines with Bicarbonate Ions: Formation of N-Carbamates and 2-Oxazolidones in Cell Culture Media and Blood Plasma

1H NMR spectroscopic methods have been applied to compare the in vitro reactivity of the renal papillary nephrotoxin 2-bromoethanamine (BEA) with those of selected halide-substituted nephrotoxic analogues, 2-chloroethanamine (CEA), 2-fluoroethanamine (FEA), and 1-phenyl-2-iodoethanamine (PIEA). The primary 1H NMR-detectable transformation during a 24 h incubation of confluent Madin Darby canine kidney (MDCK) cells with BEA, CEA, and FEA (at concentrations up to the IC50 determined by neutral red uptake) was the appearance in cell culture media of 2-oxazolidone (OX). Additional novel signals assigned as FEA carbamate (N-carbanoyl-2-fluoroethanamine) were observed in media collected following incubation of cells with FEA. We propose that N-carbamate intermediates are formed from the spontaneous reaction of these haloalkylamines with HCO3–buffered growth media and that OX is formed from the carbamate via elimination of the hydrogen halide. Further 1H NMR experiments, conducted for up to 8 h at 25 deg C on 5 mM solutions of BEA, CEA, and FEA in (2)H2O containing a 20-fold excess of HCO3- at pH 7.6, demonstrated a time-dependent decrease in the concentration of the free haloalkylamines accompanied by the production of N-carbamate intermediates and OX. Under these pseudo-first-order reaction conditions, the formation of OX from BEA was complete within approximately 6 h. In similar reaction conditions OX formation from CEA (24 h after initiation) had reached 54 percent of its final equilibrium concentration. Equivalent experiments demonstrated that PIEA was almost completely converted to 4-phenyl-2-oxazolidinone (PHOX) within 2 h. These observations reveal the strong disposition of this series of haloalkylamines toward reaction with HCO3- and indicate that the compounds in this family may exist only transiently as free amines in vivo, where there will virtually always be excess HCO3-. The physiological relevance of the in vitro findings is further indicated by the NMR-detectable conversion of BEA to OX and also an alkylating aziridine (AZ) moiety in rat plasma containing BEA. The ability to form carbamoylated species and OX (or PHOX) may mediate the toxicity of this series of haloalkylamines and hence is potentially of considerable significance.

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The stereoselective total synthesis of (-)-dihydrotetrabenazine

A highly stereoselective synthesis of (-)-dihydrotetrabenazine has been accomplished using (R)-tert-butanesulfinamide as a chiral source. The synthesis involves the allylation of chiral N-sulfinyl imine followed by ring closure of the resulting secondary amide with a tethered halide and the Evans-Aldol reaction as key steps.

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Modular Synthesis of Diverse Natural Product-Like Macrocycles: Discovery of Hits with Antimycobacterial Activity

A modular synthetic approach was developed in which variation of the triplets of building blocks used enabled systematic variation of the macrocyclic scaffolds prepared. The approach was demonstrated in the synthesis of 17 diverse natural product-like macrocyclic scaffolds of varied (12?20-membered) ring size. The biological relevance of the chemical space explored was demonstrated through the discovery of a series of macrocycles with significant antimycobacterial activity.

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Heat-Resistant Polymers and Composites on the Basis of Epoxy?Isocyanate Binding Agents

Abstract: The polymerization reaction of bi- and trifunctional epoxy resins with di- and polyisocyanates with different structures is studied via differential scanning calorimetry and IR spectroscopy. Polymers and composite materials (organic plastics) with high values of glass transition point, modulus of elasticity, and strength are obtained.

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