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The capacity of hydrazone bonds to readily undergo component exchange processes sees their extensive utilization in dynamic combinatorial chemistry. The kinetics of hydrazone exchange are optimal at pH ?4.5, which limits the use of hydrazone-based dynamic combinatorial libraries, particularly for biological targets which are only stable at near-neutral pH values. It would thus be advantageous if hydrazone exchange proceeded with faster rates at pH values closer to neutral. We experimentally and computationally evaluated the hypothesis that hydrazones possessing neighbouring acidic or basic functional groups within the carbonyl-derived moitety of the hydrazone would enhance exchange rates. Our work suggests that judiciously placed N- or O-hydrogen bond acceptors within the carbonyl-derived moiety of the hydrazone stabilize transition states via hydrogen bonding interactions, providing a valuable boost to exchange kinetics at near-neutral pH values. We anticipate these findings will be of interest in dynamic combinatorial chemistry, dynamic covalent polymers/materials, functionalized nanoparticles and interlocked molecules, all of which may benefit from hydrazone exchange processes able to operate at near-neutral pH values.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Isothiocyanate complexes of Zn(II) and Cd(II) with the condensation product of 2,6-diacetylpyridine and trimethylammoniumacetohydrazide (Girard?s T reagent) were synthesized, characterized, and their antimicrobial activities were evaluated. The structures of the complexes were determined by elemental analysis, IR, and NMR spectroscopy. The crystal structure of the Zn(II) complex was also determined. Quantum-chemical calculations of the geometry and total energy of isomers of 2,6-diacetylpyridine-bis(trimethylammoniumacetohydrazone) were performed in vacuum and methanol solution, with the aim to explain conformational behavior and E/Z isomerism of this compound. DFT calculations of the molecular structures and the relative stabilities of linkage isomers of the Cd(II) complex showed that the isomer with N?Cd?N coordination of SCN? is the most stable. Complexes of Zn(II) and Cd(II) exhibited low to moderate activity against the tested microbial strains.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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The isothiocyanato Fe(III) complex with (E)-N,N,N-trimethyl-2-oxo–2-(2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)ethan-1-aminium was synthesized and characterized by elemental analysis, IR spectroscopy and X-ray analysis. The octahedral geometry of the Fe(III) complex consists of the deprotonated form of the hydrazone ligand coordinated through the pyridine nitrogen, azomethine nitrogen and carbonyl oxygen atoms with three isothiocyanato ligands in the remaining coordination places. The measured effective magnetic moment for Fe(III) complex corresponds to high spin Fe(III) ion. The hydrazone ligand and its Fe(III) complex showed lower activity against the tested microbial strains than standard antimicrobial drugs.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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RATIONALE Prostaglandin E2 is an important biomarker in many biological systems. The development of sensitive and reliable analytical methods for monitoring PGE2 contents in various samples is of great interest. Here we developed an improved method for evaluating the enzyme activity and screening COX-2 inhibitors using ultrahigh-performance liquid chromatography/tandem mass spectrometry (UPLC/MS/MS) combined with PGE2 derivatization. METHODS Girard’s reagent-T was used as the derivatization reagent and the reaction conditions were optimized. The established method was performed to screen the COX-2 inhibitors from effective constituents of herbs and detect the concentration of PGE2 in biological tissue samples (liver and kidney). The IC50 values of celecoxib, rofecoxib, sinomenine, bulleyaconitine A, tetrandrine, fangchinoline, berberine hydrochloride and sophocarpidine towards COX-2 were determined. RESULTS This method improves the quantitative ability for PGE2, including the linearly dependent coefficient, linearity range and limit of detection. After derivatization, the derivatized PGE2 could be detected in positive ion mode of electrospray ionization (ESI), which improves the detection sensitivity 10-fold compared to that of the direct detection of underivatized PGE2 in negative ESI mode. Besides the positive control, sinomenine (IC50 = 113 muM) and bulleyaconitine A (IC50 = 53 muM) were found to be potent COX-2 inhibitors. CONCLUSIONS All the results indicate that the present derivatization quantification method of PGE2 could be used as the detection method of COX-2 enzyme activity and as the screening method for COX-2 inhibitors.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Synthesis, characterization and antimicrobial activity of pentagonal-bipyramidal isothiocyanato Co(II) and Ni(II) complexes with 2,6-diacetylpyridine bis(trimethylammoniumacetohydrazone)

Pentagonal-bipyramidal isothiocyanato Co(II) and Ni(II) complexes with condensation product of 2,6-diacetylpyridine and trimethylammoniumacetohydrazide (Girards T reagent) were synthesized and characterized by elemental analyses, IR and UV-vis spectra, molar conductivity, and magnetic susceptibility. Crystal structures of the Co(II) and Ni(II) complexes were also determined. Antimicrobial activities of the ligand and metal complexes were examined.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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AZULENYL NITRONE SPIN TRAPPING AGENTS, METHODS OF MAKING AND USING SAME

The present invention provides azulenyl nitrones, such as those having the following general formula: (I) compositions comprising the same and methods of their use for the treatment or prevention of oxidative, ischemic, ischemia/reperfusion-related and chemokine-mediated conditions.

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Metal catalyst and ligand design,
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1-chloroacetyloxindole(isatin) in reactions with some N-nucleophiles. Unexpetedly easy cleavage of chloroacetyl group

Reactions of 1-chloroacetyloxindole and 1-chloroacetylisatin with some secondary amines, Girard?s reagent T and thiourea were studied. All investigated reactions proceeded via cleavage of the acyl group to form 3-substituted isatin or oxindole derivatives.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Electron-deficient DNA-intercalating agents as antitumor drugs: Aza analogues of the experimental clinical agent N-[2- (dimethylamino)ethyl]acridine-4-carboxamide

A series of azaacridine (benzonaphthyridine) analogues of the drug N-[2- (dimethylamino)ethyl]acridine-4-carboxamide (DACA) (currently in clinical trial) were synthesized. These compounds showed DNA binding affinities similar to that of DACA, as determined by the fluorometric ethidium displacement assay, but were generally less potent cytotoxins against P388 leukemia in vitro. The only compounds showing higher cytotoxicity than DACA were analogues with nitro substituents at the (acridine) 1-position; by analogy with the 1-nitroacridine nitracrine, these compounds probably undergo reductive metabolism. The only azaacridine to show significant in vivo antileukemic activity was benzo[b] [1,5]nephthyridine-6-carboxamide. A possible reason for the unexpectedly low activity of these compounds (given the wide acceptability of substituents in DACA) may be their much lower lipophilicities, which are likely to result in lower rates of cell uptake.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Synthesis and NMR and mass spectrometric study of ammonioacetohydrazones of formylphenylboronic acids as novel ionic prospective sugar receptors

Novel sugar-sensing, soluble in aqueous media, boronic acid derivatives designed for easy analysis through MALDI mass spectrometry have been synthesized in a high yield through a mild and efficient procedure. The synthesized compounds are based on formylphenylboronic acids, which can bind through the formyl group with acid hydrazides to form the respective hydrazones. As hydrazide substrates, Girard reagents T and P were chosen, which possess precharged ammonium and pyridinium moieties, respectively. Nuclear magnetic resonance spectroscopy (1H, 13C, HSQC, HMBC, and NOESY) and mass spectrometry were employed to study their structure, conformational equilibrium and interaction with selected sugars and other diols. Our study shows that the ammonioacetohydrazones of formylphenylboronic acids are present in DMSO solution in the form of cis/trans amide conformers and the effectiveness of their interaction with sugars depends on the situation of the substituent in relation to the boronic acid group. Introducing an ionic group to the receptor molecule improves the sensitivity for conjugate detection when analyzed by MS with matrix-assisted laser desorption/ionization (MALDI) in the positive-ion mode.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI