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(E)-4-(3-phenylisoxazol-5-yl)but-3-en-2-one

(E)-4-(3-Phenylisoxazol-5-yl)but-3-en-2-one was synthesized via the oxidative ring opening reaction of 2-(5-methylfuran-2-yl)-1-phenylethanone oxime, followed by the iodine mediated isomerization.

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Thermodynamic properties and ideal-gas enthalpies of formation for cyclohexene, phthalan (2,5-dihydrobenzo-3,4-furan), isoxazole, octylamine, dioctylamine, trioctylamine, phenyl isocyanate, and 1,4,5,6-tetrahydropyrimidine

The results of a study aimed at improvement of the group-contribution methodology for estimation of thermodynamic properties of organic substances are reported. Specific weaknesses where particular group-contribution terms were unknown, or estimated because of lack of experimental data, are addressed by experimental studies of enthalpies of combustion in the condensed phase, vapor-pressure measurements, and differential scanning calorimetric (dsc) heat-capacity measurements. Ideal-gas enthalpies of formation of cyclohexene, phthalan (2,5-dihydrobenzo-3,4-furan), isoxazole, octylamine, dioctylamine, trioctylamine, phenyl isocyanate, and 1,4,5,6-tetrahydropyrimidine are reported. Two-phase (liquid + vapor) heat capacities were determined for phthalan, isoxazole, the three octylamines, and phenyl isocyanate. Liquid-phase densities along the saturation line were measured for phthalan and isoxazole in the temperature range 298 K to 425 K. The critical temperature and critical density of octylamine were determined from the dsc results and a critical pressure derived from the fitting procedures. Fitting procedures were used to derive critical temperatures, critical pressures, and critical densities for cyclohexene (pressure and density only), phthalan, isoxazole, dioctylamine, and phenyl isocyanate. Group-additivity parameters or ring-correction terms useful in the application of the Benson group-contribution correlations are derived.

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Synthesis and characterization of some isoxazole derivatives for antimicrobial activity

In the present work, some newer 3,5-substituted diphenyl isoxazole derivatives (compounds 1-10) were synthesised by reaction of hydroxylamine hydrochloride with various freshly synthesised 1-(substituted phenyl)-3-(substituted phenyl)prop-2en-1-one derivatives (compounds. 1A-10A) in the presence of pyridine and catalytic amount of sodium hydroxide. Compounds 2, 4, 5, 10 were found to possess good antibacterial activity and compounds 3 and 10 showed good antifungal activity when compared with standard drugs ciprofloxacin and fluconazole at the concentration 50 mug mL-1. These results suggest that the synthesized isoxazole derivatives exhibit promising activity and this work may pave the way for future development of promising compounds for this purpose.

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Palladium-catalyzed site-selective direct olefination of 6-electron-withdrawing group substituted 3-arylbenzo[: D] isoxazoles

A palladium-catalyzed direct olefination of 6-electron-withdrawing group substituted 3-arylbenzo[d]isoxazoles has been developed with exclusive site-selectivity and excellent E-stereoselectivity. It was found that the olefination occurred at the acidic C-7 position only, overriding a potential directing-group assisted bias. With the wide range of alkene patterns, the protocol allows convenient access to multifarious C-7 olefinated benzo[d]isoxazoles in moderate to good yields.

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Isoquinolinylpyrazoles and pyridylisoxazoles as luminescent materials with sensorial ability towards pollutant toxic metal ions. Experimental and computational studies

The crystal structure and photoluminescence behaviour of two series of azole-based derivatives have been investigated. In the solid state, the compounds form head-to-tail dimers through intermolecular hydrogen bonds and emit bluish light in the range of 340?500 nm. The geometry parameters have been optimised by DFT calculations to analyse the molecular electrostatic potential (MEP) and the charge distribution in order to find the favourable molecular sites for metal interactions. The electronic properties of the frontier orbitals and their energy levels have been also measured. The compounds behave as fluorescent materials in solution and they exhibit sensorial abilities towards Hg2+, Pd2+, Pt4+, Cu2+, Zn2+ and Cd2+ metal ions. The ion sensing properties that the azoles present upon complexation have been followed by spectrophotometric and spectrofluorimetric titrations. Additionally, the stability constants of the complexes formed as well as the detection and quantification limits have been calculated. The best results are obtained for the detection of Zn2+ at concentration lower than 0.3 muM.

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Antibacterial activity, computational analysis and host toxicity study of thymol-sulfonamide conjugates

Methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin resistant Enterococcus faecalis (VRE) are notorious pathogenic multidrug resistant (MDR) bacteria in both hospital and community sectors, and today the first antibacterial drug sulfamethoxazole is ineffective. The monoterpene phenol, thymol was conjugated with seven sulfa drug derivatives individually, adopting the dye-azo synthesis protocol, and conjugates were characterized using spectral analysis techniques such as, UV, FTIR, MS, HPLC, 1H NMR, 13C NMR and SEM. Conjugates were assessed for antibacterial activity in vitro and in silico; the zone of inhibition, MIC and MBC values of each conjugate were determined against isolated MRSA and VRE strains from clinical samples. As 3-dimentional structures of dihydropteroate synthases (DHPSs) of targeted bacteria are not available in protein database, homology models of DHPS enzymes of both bacteria were generated and validated by Ramachandran plots. Seven conjugates were used as ligands in molecular docking against MRSA-DHPS and VRE-DHPS. Additionally bioinformatics tools, PASS prediction, Lipinski rules of five, computational LD50 value, toxicity class, HOMO, LUMO and EPS plots were carried out to assess standard drug-likeliness properties of conjugates. Zone size inhibition of the conjugate, 4b (thymol?+?sulfadiazine) against MRSA and VRE strains on agar plates were 20 and 40?mug/mL as the lowest MIC and MBC values, respectively; while the reference antibiotic ampicillin had the lowest MIC and MBC values at 80 to 180?mug/mL. In vitro host-toxicity testing was carried out with cultured human-lymphocytes from umbilical cord blood, and 4b was broadly non-toxic to human cells at 15,000?mg/L. Thus, 4b could be promoted a newer antibacterial, against gruesome MDR bacteria.

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Structural and Hirshfeld surfaces of thiophene based isoxazole derivatives: 3-(3-Methylthiophen-2-yl)-5-(3,4,5-trimethoxyphenyl)isoxazole and 5-(3-Methylthiophen-2-yl)-3-(3,4,5-trimethoxyphenyl)isoxazole

The title compounds C17H17NO4S (I) and C17H17NO4S(II) crystallized in the monoclinic system with the space group of P21/c. The dihedral angles of 8.88(2)? and 10.54(13)? are observed between their terminal rings for I and II, respectively. Intramolecular hydrogen bonds form a pair of S(6) ring motifs in (I) and three S(6) ring motifs in (II). The crystal structure is stabilized by short intermolecular hydrogen bonds generating ring motifs of the type R2 2(12) (I) and R1 2(5) (II). Overall packing form a 3D supramolecular network in (I) and layer stacking along b axis in (II). The intermolecular interactions and their percentage of contributions were quantified for both the compounds using Hirshfeld surfaces.

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Syntheses and Biological Properties of Pyrido[3,4-b]homotropane (PHT) and its Analogues with Bridged Aza-[n.2.1] Skeletons

The nicotinic acetylcholine receptor (nAChR) is one of the targets for developing drugs for the treatment of central nervous system (CNS) disorders and for control of agricultural pests. Pyrido[3,4-b] homotropane (PHT) was originally designed and synthesized by Kanne and co-workers and showed strong affinity binding to nAChR. PHT has a novel aza-[4.2.1]nonane skeleton. Owing to its excellent biological activities and novel chemical structure, synthetic and medicinal chemists have been attracted by this molecule. Some PHT analogues with bridged aza-[n.2.1] skeletons were also designed and synthesized via different strategies. Herein, we summarize the syntheses of PHT and its analogues. Their biological activity study is also briefly discussed.

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Long-Range 1H-15N Heteronuclear Shift Correlation

The investigation of long-range 1H-15N heteronuclear shift correlation NMR experiments has gone from its inception in 1995 to a robust area of research with numerous studies now reported annually. The area has been reviewed twice, covering the literature through about mid-2000. The present report covers the period from where this author’s previous review stopped in late-1999 through the present. New long-range heteronuclear shift correlation methods that are applicable to long-range 1H-15N 2D heteronuclear shift correlation are discussed followed by a discussion of the impact of long-range 1H-15N data on Computer-Assisted Structure Elucidation methods and then a review of the applications of these techniques reported in the literature.

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Ruthenium(II)- and Copper(II)-Mediated Synthesis of Trisubstituted Pyrroles from Isoxazoles and Acrylate Esters

An efficient ruthenium(II)- and copper(II)-mediated, ?one-pot? synthesis of pyrroles has been reported. The reaction most probably proceeds via a reductive cleavage of isoxazoles. This protocol results in the synergistic formation of new C?C, C?N bonds, which leads to a simple and an efficient method for the synthesis of highly functionalized pyrroles from isoxazoles and acrylate esters.

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