• Journal of the Korean Chemical Society
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• v.54 no.6
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• pp.731-736
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• 2010

Several new 5-aryl-3-($\beta$-D-glucopyranosylthio)-1,2,4-triazoles have been synthesized. The structures of these new compounds were confirmed by $^1H$ NMR, $^{13}C$ NMR and elemental analyses.The antibacterial activities of the compounds were also evaluated.

• Archives of Pharmacal Research
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• v.13 no.2
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• pp.142-146
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• 1990

Reaction of ethyl 4-chloro-2-phenylpyrimidine-4-carboxylate (4) with 5-chloro-2-methylthiophenol or 3-aryl-4-phenyl-1, 2, 4-triazole-5 thiol yielded the corresponding thioethers (5) and (8a, b), respectively. Careful alkaline hydrolysis of (5) yielded the corresponding carboxylic acid (6). Reaction of (4) with p-aminoacetophenone yielded compound (10) which was reacted with certain aromatic aldehyde to afford the$\alpha,\beta$-unsaturated ketones (11a-d). Condensation of (11a-d) with malononitrile or phenylhydrazine yielded the 2-amino-3-cyanopyridines (12a-f) or the 2-pyrazolines (13a, b) respectively. Seven representative compounds were tested for their in vitro antimicrobial activity against some pathogenic micro-organisms, some of them were proved to be active.

• Bulletin of the Korean Chemical Society
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• v.31 no.7
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• pp.1843-1847
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• 2010

An efficient method for the preparation of 1,4-disubstituted 1,2,3-triazole compounds is described using polymeric quaternary ammonium salts having azide or alkyne functionality to remove unreacted excess starting molecules (azide/alkyne). Copper metal could easily be removed by simple filtration with a short $Na_2SO_4$/silica cartridge, affording highly regioselective products in high yield and excellent purity without the need for work-up, extraction and chromatographic purification.

• Bulletin of the Korean Chemical Society
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• v.32 no.8
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• pp.2657-2660
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• 2011

1,2,4-Triazoles and quinoxalines were found to display various pharmacological activities. Hence a series of 1-aryl-4-methyl-1,2,4-triazolo[4,3-a]quinoxalines were synthesized. Due to various advantages of organic reactions under solvent-free conditions these compounds were developed using iodobenzene diacetate under solvent-free conditions. The synthesized compounds were characterized by elemental microanalysis, infrared spectroscopy, $^1H$ NMR, $^{13}C$ NMR and HRMS. All the synthesized compounds were investigated for their antitubercular activity and 5g was found to the most active compound.

• Archives of Pharmacal Research
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• v.28 no.4
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• pp.438-442
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• 2005

A series of 3-[1-(4-(2-methylpropyl) phenyl) ethyl]-1,2,4-triazole-5-thione (I) and its bicyclic condensed derivatives 6-benzylidenethiazolo[3,2-b]-1, 2,4-triazole-5(6H)-ones (IIa-IIf) were investigated for the prevention of ethanol-induced oxidative stress in liver and brain of mice. Administration of ethanol (0.1 mL/mice, p.o.) resulted in a drop of total thiol groups (T-SH) and non-protein thiol groups (NP-SH), and an increase in thiobarbituric acid reactive substances (TBARS) in both liver and brain tissue of mice (p<0.001). Among the compounds investigated (at a dose of 200 mg/kg, p.o.), I and IId ameliorated the peroxidative injury in these tissues effectively. Compounds IIa, IIc and IIe improved the peroxidative tissue injury only in brain. These findings suggest that certain condensed thiazolo-triazole compounds may contribute to the control of ethanol-induced oxidative stress in an organ selective manner.

• Bulletin of the Korean Chemical Society
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• v.29 no.8
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• pp.1561-1564
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• 2008

Although the use of Cu(II) salts as catalysts without reductants is limited in the cycloaddition of acetylenes with azides, the catalytic system employing average 10 nm CuO(II) nanoparticles in the absence of reductants shows good catalytic activity to form 1,4-disubstituted 1,2,3-triazoles even in wet THF as well as water. It is also noticeable that CuO(II) nanoparticle catalysts can be recycled with consistent activity. A range of alkynes and azides were subject to the optimized CuO(II) nanoparticle-catalyzed cycloaddition reaction conditions to afford the desired products in good yields.

• Journal of the Korean Chemical Society
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• v.32 no.4
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• pp.301-310
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• 1988

Reaction rates for mononuclear heterocyclic rearrangement of N-(5-phenyl-1,2,4-oxadiazol-3-yl)-N'-arylformamidines into 3-acylamino-1-aryl-1,2,4-triazoles were determined spectrophotometrically in dioxane/water (50 : 50, v/v). There are two different reaction paths according to pH. One is pH-independent path, the other is pH-dependent one. In pH-independent path, the result of substituent effect by IYT equation show that N-H bond breaking as well as new N-N bond formation controls the reaction rate. In pH-dependent path, concave-upward Hammett plot was observed. It can be concluded that new N-N bond formation is more advanced than N-H bond breaking in transition state for electron-donating substituents, but N-H bond breaking is more advanced than new N-N bond formation for electron-withdrawing substituents.

• Bulletin of the Korean Chemical Society
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• v.33 no.8
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• pp.2603-2608
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• 2012

A novel mononuclear supramolecule of copper(II) has been synthesized with Ippyt ligand (Ippyt=3-(4'-imidazole phenyl)-5-(pyrid-2''-yl)-1,2,4-triazole) (1). Compound 1, namely [$Cu(Ippyt)_2(H_2O)_2$], has been characterized by single-crystal X-ray diffraction, IR spectrum, elemental analysis and thermogravimetric analysis. Structure determination reveals that the elongated-octahedral geometry is formed in the vicinity of the copper (II) atom being coordinated by four nitrogen atoms from two Ippyt ligands occupying the equatorial position and two oxygen atoms from two coordinated water molecules in the axial position, which together form the $N_4O_2$ donor set. Hydrogen bonding interactions between nitrogen and oxygen atoms result in the set up of a supramolecular network architecture. Biological properties including antibacterial activity and superoxide dismutase (SOD) mimetic activity of compound 1 have been investigated by agar diffusion method and the modified Marklund method, respectively. The results indicate that compound 1 exhibits a stronger antibacterial efficiency than the parent ligand and it also has a certain radical-scavenging activity.

• Archives of Pharmacal Research
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• v.29 no.10
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• pp.826-833
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• 2006

Previously, we synthesized and evaluated several benzofuran derivatives containing heterocyclic ring substituents linked to the benzofuran nucleus at C-2 by a two- to four-atom spacer as potential anti-HIV-1, anticancer and antimicrobial agents. Among these derivatives, NSC 725612 and NSC 725716 exhibited interesting anti-HIV-1 activity. To further investigate the structure-activity relationship, we synthesized several new benzofuran derivatives derived from 2-acetylbenzofuran (2, 3a-c) and 2-bromoacetylbenzofuran (6; 7a,b; 8a,b). The compounds were designed to comprise the heterocyclic substituents directly linked to the benzofuran nucleus at C-2. Moreover, various related benzimidazoles derived from 2-acetylbenzimidazole and from 2-cyanomethylbenzimidazole (12a,b; 13a,b; 15; 16a,b) were also prepared as isosteres. The synthesized compounds were preliminarily evaluated for their in vitro anti-HIV-1, anticancer and antimicrobial activity. Compounds 2, 3a, 3b, and 12b showed weak anti-HIV-1 activity. Compound 6 exhibited mild activity against S. aureus, while compound 15 had mild activity towards S. aureus and C. albicans. However, no significant anticancer activity was observed with any of the tested compounds. From these results, we conclude that the presence of the spacer between the heterocyclic substituent and the benzofuran nucleus may be essential for the biological activity.