53788-34-4Relevant academic research and scientific papers
Tuning the sensitivity towards mercury: Via cooperative binding to d-fructose: Dual fluorescent chemosensor based on 1,8-naphthyridine-boronic acid derivative
Rajadurai, Marina,Reddy, E. Ramanjaneya
, p. 14862 - 14870 (2021/05/19)
A novel fluorescent chemosensor naphthyridine-boronic acid derivative (1.1) was synthesized and its ability to act as a selective chemosensor was examined for various metal ions. Compound 1.1 displayed highly selective fluorescence quenching upon interaction with Hg2+, possibly by means of photo induced electron transfer (PET) mechanism. The binding stoichiometry of the naphthyridine-boronic acid-Hg2+ complex and the association constant was determined. It was found that in the presence of d-fructose at physiological concentration, the sensitivity of chemosensor 1.1 towards Hg2+ improved by at least 7 times, perhaps as a result of the cooperative binding of both d-fructose and mercury ion to the sensor. Till now, the presented dual d-fructose-mercury chemosensor is the first example of utilizing boronic acid-diol complexation for enhancement of the sensor's sensitivity towards a toxic metal ion. The utility of compound 1.1 lays in applications in the food industry, e.g. for detection of mercury contamination of high fructose corn syrup, or in estimation of mercury in polluted biological samples and underground water. This journal is
Naphthyridine-based iridium complexes: Structures and catalytic activity on alkylation of aryl ketones
Chen, Po-Hao,Liu, Yi-Hung,Liu, Shiuh-Tzung
, p. 972 - 981 (2019/05/24)
Iridium(III) complexes containing a designed ligand, 2-amino-7-(2-pyridinyl)-1,8-naphthyridine derivative, were prepared and all complexes were characterized using spectroscopic and crystallographic methods. These new Ir(III) complexes are able to act as catalysts for the C-alkylation of aryl alkyl ketones with the use of alcohols as the alkylating agent. Typically, acetophenone undergoes alkylation with methanol and ethanol to yield isobutyrophenone and butyrophenone, respectively.
Light-driven artificial enzymes for selective oxidation of guanosine triphosphate using water-soluble POSS network polymers
Jeon, Jong-Hwan,Tanaka, Kazuo,Chujo, Yoshiki
, p. 6500 - 6506 (2014/08/18)
The light-driven artificial enzymes were constructed to realize unnatural reactions concerning bio-significant molecules. In this manuscript, the guanosine triphosphate (GTP)-selective oxidation is reported using the network polymers composed of polyhedral oligomeric silsesquioxane (POSS). We synthesized the water-soluble POSS network polymer containing the naphthyridine ligands to capture GTP inside the networks and the ruthenium complexes to oxidize the captured GTP under light irradiation. Initially, the binding affinities of the guanosine nucleosides to the naphthyridine ligand inside the POSS network polymer were evaluated from the emission quenching experiments. Accordingly, it was observed that the naphthyridine ligand can form the stable complex only with GTP (Ka = 5.5 × 106 M-1). These results indicate that only GTP can be captured by the network polymer. Next, the photo-catalytic activity of the ruthenium complex-modified POSS network polymer was investigated. Finally, it was revealed that the network polymer can decompose GTP efficiently under light irradiation. This is the first example, to the best of our knowledge, to offer not only the GTP-selective host polymers but also the light-driven artificial enzyme for GTP oxidation. the Partner Organisations 2014.
Synthesis and evaluation of fluorogenic 2-amino-1,8-naphthyridine derivatives for the detection of bacteria
Varadi, Linda,Gray, Mark,Groundwater, Paul W.,Hall, Andrew J.,James, Arthur L.,Orenga, Sylvain,Perry, John D.,Anderson, Rosaleen J.
, p. 2578 - 2589 (2012/04/23)
Several novel fluorogenic N-aminoacylnaphthyridine substrates were synthesized in good yield and tested for their ability to detect pathogenic bacteria in agar-based cell culture. Simple 2-N-(β-alanyl)amino-5,7- dialkylnaphthyridine substrates were selectively hydrolysed by β-alanylaminopeptidase expressing bacteria, but were subject to diffusion in the agar medium. Diffusion was reduced in the 2-N-(β-alanyl)amino-7- alkylnaphthyridine substrates with longer alkyl chains, but inhibition of growth was increased. 2-N-(β-Alanyl)amino-7-octylnaphthyridine inhibited the growth of all species tested, except for strains resistant to colistin/polymyxin, providing a rationale for the development of substrates for the selective detection of drug resistant species in clinical samples. The Royal Society of Chemistry 2012.
Preparation of 2,7-diamino-1,8-naphthyridine: A useful building block for supramolecular chemistry
Park, Taiho,Mayer, Michael F.,Nakashima, Shoji,Zimmerman, Steven C.
, p. 1435 - 1436 (2007/10/03)
A two-step conversion of 2-chloro-7-amido-1,8-naphthyridine to 2,7-diamino-1,8-naphthyridine is described. The process, which involves a nucleophilic aromatic substitution reaction with 4-methoxybenzylamine and subsequent deprotection, can be carried out
Complexation-induced unfolding of heterocyclic ureas. Simple foldamers equilibrate with multiply hydrogen-bonded sheetlike structures
Corbin,Zimmerman,Thiessen,Hawryluk,Murray
, p. 10475 - 10488 (2007/10/03)
The synthesis and conformational studies of heterocyclic ureas (amides) 1-7 and their concentration-dependent unfolding to form multiply hydrogen-bonded complexes are described. Ureas 1 and 7 were prepared by reacting 2-aminopyridine and aminonaphthyridine 25, respectively, with triphosgene and 4-(dimethylamino)-pyridine (DMAP). Amine 25, in turn, was synthesized by a Knorr condensation of 2,6-diaminopyridine and 4,6-nonanedione. Heterocyclic ureas 3, 4, and 16 were prepared by treating their corresponding amino precursors with butylisocyanate, whereas bisureido naphthyridines 6 and 17 were prepared by heating 2,7-diamino-1,8-naphthyridine (13) with butylisocyanate and 3,4,5-tridodecyloxyphenyl isocyanate, respectively. The hydrogen-bonding modules 2 and 5 were synthesized by reacting 13 and 2-amino-1,8-naphthyridine with valeric anhydride. X-ray crystallographic analyses were performed on ureas 1, 3, 16, and 17, indicating that these ureas are intramolecularly hydrogen-bonded in the solid state. Moreover, detailed 1H NMR solution studies of 1, 3, 4, 6, and 7 indicate that similar folded structures form in chloroform. In addition, naphthyridinylureas 3 and 7 unfold and dimerize by forming four hydrogen bonds at high concentrations, and ureas 1 and 4 unfold in the presence of their hydrogen-bonding complements, amides 2 and 5, to form Complexes with three and four hydrogen bonds, respectively. Likewise, the mixing of 6 and 7 results in a mutual unfolding and formation of a robust, sheetlike, sextuply hydrogen-bonded complex. The hydrogen-bonding modules described are useful building blocks for self-assembly, and the unfolding process represents a very primitive mimicry of the helix-to-sheet transition shown by peptides and potentially shown by the hypothetical naphthyridinylurea 8.
Naphthyridine derivatives
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, (2008/06/13)
Compounds of the formula: STR1 wherein one of the symbols =X-- represents =N-- and the other three each represent a group STR2 in which Y represents hydrogen, halogen, alkyl, alkoxy, cyano or nitro, at least two of the symbols representing hydrogen, Z represents hydrogen, halogen, alkyl, alkoxy, trifluoromethyl or nitro, and (i) n represents zero and R represents hydrogen, alkyl, alkenyl, alkynyl, hydroxyalkyl or phenyl, or (ii) n represents 1 and R represents alkyl, hydroxyalkyl or phenyl, are new compounds possessing pharmacological properties; they are particularly active as tranquilizers and anti-convulsant agents.
1,4-Dithiino(2,3-c)pyrrole derivatives
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, (2008/06/13)
New compounds of the formula: SPC1 Wherein A is a phenyl, pyridyl, pyridazinyl, 2-, 3- or 4-quinolyl or naphthyridinyl radical, or a said radical substituted by one or two atoms or radicals selected from halogen, alkyl, alkoxy cyano and nitro, R is alkyl, alkenyl or hydroxyalkyl, and n is zero or 1, possess pharmacological properties and are, in particular, active as tranquilisers, anti-convulsant agents, decontracturants and agents to produce hypnosis.
